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3%% This page has been alphabetized. Please add new examples in the correct order. Thanks!
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7->'''Lily:''' Barney, how can you be in love and still be sleeping with anything that moves?\
8'''Barney:''' I'm sorry, I don't follow you. That's like saying, "How can an ant carry twenty times its body weight, but root beer floats are still delicious?" Are the two even related?
9-->-- ''Series/HowIMetYourMother''
10
11TheCasanova has scored dozens of women, [[ConfirmedBachelor never showing any real affection]] for any of them. However, maybe one of the girls, for whatever reason, is [[ILoveYouBecauseICantControlYou immune to his charms]]. Maybe he [[DefrostingIceQueen initially hates the girl, but then comes to appreciate her]]. Or maybe he's beginning to [[RelationshipUpgrade develop romantic feelings]] for a [[JustFriends female friend of his]].
12
13Basically, the man([[LovableSexManiac whore]]) ''genuinely'' [[CharacterDevelopment falls in love]].
14
15It can be played for quite a lot of angst -- how will the HandsomeLech convince his LoveInterest that he's being genuine? Usually, this trope either [[JerkWithAHeartOfGold humanizes]] or [[BadassDecay defangs]] the character. A staple for RomanticComedy. Nine of ten male protagonists in Hispanic ''[[SoapOpera Telenovelas]]'' follow this trope and if the lead character of a ChickFlick is a man, you ''will'' see this in action.
16
17A common effect is that the charming ways that made these guys such winners with the ladies fall apart under the pressure of really wanting to charm her: fluent flirtation turns to GibberishOfLove and/or CanNotSpitItOut.
18
19Most of the time, the characters give up their perverted ways for love; however, it's becoming more common for them to maintain their flirtatiousness (for the most part), but have it toned down for the sake of their love interests.
20
21Compare InconvenientAttraction, ReformedRakes, LookingForLoveInAllTheWrongPlaces. CantActPervertedTowardALoveInterest can result from this, and if combined with MadonnaWhoreComplex, the Casanova themselves may be the one who SleepsWithEveryoneButYou. See also MoreExperiencedChasesTheInnocent, which often involves a ladykiller pursuing a sexually and/or romantically inexperienced person and eventually falling in love with them.
22----
23!!Examples:
24
25[[foldercontrol]]
26
27[[folder:Anime & Manga]]
28* Roybea Roy of ''Anime/AfterWarGundamX'' is nicer than most Casanovas in that he genuinely cares for all of his girlfriends even though they are numerous and temporary, but he carries a torch for Sala for quite a while. She views him as a good guy but has a SubordinateExcuse for Captain Jamil and Roybea is quite aware of that. [[spoiler:Eventually, after she turns him down for good and he decides to respect such a decision, he switches his affections to Ennil El instead, and they're still together in the epilogue.]]
29* Sayoko Mishima of ''Manga/AhMyGoddess'' is a gender-flipped version. She's beautiful, rich, and has all the men in the Nekomi Institute fawning over her, until [[MagicalGirlfriend Belldandy]] shows up and unwittingly steals her spotlight. She then takes to make advances on Keiichi (despite having previously rejected him when he tried to ask her out) just to spite Belldandy, which leads her to know him better, [[UnrequitedLoveSwitcheroo and before she realizes she ends up falling for him.]]
30* Go Katou from ''Manga/AiShiteNight'' has quite the [[TheCasanova ladykiller]] fame, but when he develops feelings for GirlNextDoor Yakko, he falls ''hard'' for her.
31* Raphael from ''Manga/AngelSanctuary.'' Of course, [[LoveHurts it ends badly]].
32* Apparently, both [[spoiler:Antonio Fabiani AND Leonardo Cardinale]] of ''Anime/AshitaNoNadja'', in regards to the same girl: [[spoiler:Julietta Satori]].
33* In some ''Manga/BoysOverFlowers'' continuities, the F4's resident Casanova Soujiro falls for Tsukushi's best friend Yuki.
34* Ryo Saeba, the protagonist of ''Manga/CityHunter'', is a notorious and successful Casanova in spite of his job as a ProfessionalKiller, and is in love with his partner Kaori, even if he doesn't want to admit it.
35* Sho Naruse from ''Manga/CheekyBrat'' has swarms of girls obsessing over him, but he himself is very committed to his relationship with Yuki.
36* Ian is this in ''Manga/ACruelGodReigns'', although it stinks for him that Jeremy is his ForbiddenFruit.
37* A villainous example with Sateriasis Venomania of ''Literature/TheLunacyOfDukeVenomania'', who is a Casanova of the type that [[QuestionableConsent brainwashes women into loving him and joining his harem.]] He claims to love all the women he brainwashes and doesn't see the point of just picking one; this trope is played more straight in that he has a real affection for his childhood friend, Gumina Glassred, one of the women brainwashed. It doesn't turn out well, of course.
38* ''Literature/TheFamiliarOfZero'':
39** Guiche is in love with Montmorency, but he is still a conceited playboy who makes a habit out of flirting with any beautiful girl that catches his eye.
40** Kirche may be a female version since it's strongly implied in the anime that she ReallyGetsAround -- or at least used to, before falling for Saito and, after, Mr. Colbert.
41* Indications are that this is the case for ''Literature/FullMetalPanic'''s LovableSexManiac Kurz Weber with regards to Melissa Mao, but they're not past the "slap" stage of SlapSlapKiss in the anime. [[spoiler:They finally end up together in the novels.]]
42* In ''Manga/FutariEcchi'', Matsuzaki's crush on [[LikesOlderWomen several years older]] Kyouko, where he mistakes her bossy and aloof attitude for her being experienced in sex, not knowing that she is actually a virgin.
43* Yuki from ''Manga/{{Gravitation}}'' reportedly had numerous one-night stands with women before meeting Shuichi. There's also the fact that he was reluctant to let himself love again after [[spoiler:his first love Kitazawa set him up to be gang-raped and he shot him dead in self-defense]] until Shuichi helps him overcome it.
44* In ''Manga/HappyYarouWedding'', former "King of the Night" Akira Todou falls in love with his housekeeper/nanny.
45%%* Chizuru for Azumi in ''Hen''.
46* ''Manga/HatsukoiZombie'''s Haran Koigaura fulfills the standard version of this trope in manga, except he thinks it's a gay crush, since the object of his newfound affections is [[{{Bishounen}} Ibusuki]]. He's utterly convinced he's a girl though ([[{{Bifauxnen}} he's right]]), so it's a bit complicated.
47* ''Literature/TheHeroicLegendOfArslan'' has Gieve, smooth-talking [[TheCasanova Casanova]], falling head over heels for LadyOfWar Farangis who ignores his advances.
48* Canon-wise, Greece from ''Webcomic/HetaliaAxisPowers'' might be this toward Japan, although his promiscuity isn't really his main character trait (apparently you can still be an all-around NiceGuy even if you have the honor of being at the top of sex frequency charts).
49* In ''Manga/HotGimmick'', Hatsumi's younger sister Akane is known as the 'easiest' girl around in school, to the point where when she [[MistakenForPregnant thinks that she's pregnant]], she can't decide ''which'' one of her boyfriends could have knocked her up. Later on, however, she finds herself falling for Hatsumi's sweet and unassuming friend Subaru, decides to GiveGeeksAChance, and the two end up as the series' BetaCouple.
50* ''Manga/InTheClearMoonlitDusk'': Ichimura makes it clear that despite his [[TheCasanova wealth of dating experience]], he's never really felt as attached and fixated on a girl as he does with Yoi. At first he tries to avoid it and downplay his feelings, but soon even he has to admit that he's behaving differently towards her than anyone else. It's his friends that point out he likely fell in LoveAtFirstSight.
51* [[ChivalrousPervert Miroku]] from ''Manga/InuYasha'' falls hard for [[ActionGirl Sango]]. He still hits on anything in a skirt, though. [[spoiler:They marry anyway, and he did at least stop asking other women to "bear his children" after they got engaged.]]
52* Both Tomoe and Kurama from ''Manga/KamisamaKiss'' end up falling for the heroine, Nanami.
53* WholesomeCrossdresser Kuranosuke from ''Manga/PrincessJellyfish'' towards [[LovableNerd Tsukimi]], though he's in denial at first. Tsukimi is rather [[ObliviousToLove clueless]] and ends up falling for his brother.
54* ''Manga/MonthlyGirlsNozakiKun'''s {{Bifauxnen}} Kashima Yuu is a minor example. She's a proud ChickMagnet, but in the meantime, she's constantly trying to get her drama club president and beloved upperclassman Hori's attention and worries whenever it seems like her self-proclaimed status as his "beloved kohai" is threatened.
55-->'''Kashima:''' ''(asking about the male lead of a shoujo manga she's reading)'' So I'm supposed to admire this guy like the protagonist? And he's handsome, smart, great at sports, and kind, isn't that right?
56-->'''Mikoshiba:''' Well, yeah...
57-->'''Kashima:''' ''Then why doesn't Senpai like me?! I don't get it!''
58* Katarina in ''Literature/MyNextLifeAsAVillainessAllRoutesLeadToDoom'' made sure to tell her little brother to treat girls kindly because she knew otherwise he might become a playboy. He grows into a perfect gentleman but is even more popular for it than he'd be as a shallow flirt. At one point he's heard getting frustrated that despite so many girls being into him the only one he cares about sees him as a brother and no more.
59* Never outright stated, but it's implied that Jiraiya of ''Manga/{{Naruto}}'' was [[UnrequitedLoveLastsForever in love with Tsunade, who always rejected him]]. One of his dying regrets was that he never managed to woo her.
60%%* Mariko Nakasu from ''Manga/NeighborhoodStory''.
61* In ''Manga/OnePiece'', ChivalrousPervert Sanji falls rather hard for his [[ArrangedMarriage parentally-decided spouse]] Charlotte Pudding. [[spoiler: Too bad she was a mix of HoneyTrap, WoobieDestroyerOfWorlds, and BrokenBird who counted on it.]] [[spoiler: But later she ''does'' fall for him.]]
62* Tamaki of ''Manga/OuranHighSchoolHostClub'' towards Haruhi.
63* George Koizumi in ''Manga/ParadiseKiss'', with a twist: [[spoiler:it's towards ''Kaori'' and not Yukari.]]
64* Kairi from ''Manga/PeachGirl'', toward the female lead Momo.
65* Kanba Takakura from ''Anime/{{Penguindrum}}''... towards [[BrotherSisterIncest his sister]] Himari.
66* Kail Mursili from ''Manga/RedRiver1995'', for the {{time travel}}ling lead girl Yuri. EveryoneCanSeeIt, too. And it's actually a plot point since Yuri happens to ''also'' be the one who fits the best to become Kail's NumberTwo, which makes her even more of a target from the BigBad Nakia.
67* Touga from ''Anime/RevolutionaryGirlUtena'' towards Utena. Also a {{Deconstruction}}. His love for Utena doesn't keep him from trying to control her anyway, and in the end, she doesn't love him back.
68* ''Manga/SPYxFamily'': Twilight, currently known by the name Loid Forger, is a professional spy who as a MasterActor and MasterOfDisguise has learned how to charm women for the sake of his mission and dumps them with no remorse whatsoever. Then he meets Yor, and when they end up agreeing to have [[MarriageOfConvenience a fake marriage for convenience]], he finds himself confused and trying to rationalize his growing feelings for her as being for the sake of his mission. It gets to the point that a fellow female spy who is in love with him quickly takes notice that Yor is the first and only person who [[WhenHeSmiles can make him smile genuinely]].
69* ''Anime/SuperDimensionCavalrySouthernCross'', has former 15th squad commander and notorious player, Charles de Etouard, falling madly in love with AcePilot Mary Angel.
70* ''Anime/TekkamanBlade II'' has David Kruegel, a known player who's in love with a woman he can never have: Aki Kisaragi, Takaya/D-Boy's girlfriend.
71* ''Maybe'', [[HandsomeLech Shuutarou Mendou]] from ''Manga/UruseiYatsura'' -- after he meets his rival's beautiful little sister, [[ShrinkingViolet Asuka Mizunokuji]].
72* In ''Manga/VirginLove'', Daigo becomes this after meeting [[IfItsYouItsOkay Kaoru]]. Kaoru also qualifies as a mankiller (maneater?) in love when he finally comes around.
73* In ''Manga/TheWallflower'' manga, womanizer Ranmaru is very clearly falling in love with his [[PerfectlyArrangedMarriage arranged fiancee]] Tamao (a commitment he originally tried to get out of), even if he hasn't fully realized it yet.
74* Jae-ha in ''Manga/YonaOfTheDawn'' struggles a bit with this. He's not sure if it's genuine affection for Yona or a side effect of the reincarnated Ryokuryuu's intense loyalty to Hiryuu.
75[[/folder]]
76
77[[folder:Comic Books]]
78* Believe it or not, WesternAnimation/DonaldDuck used to be a rather successful Casanova before falling for Daisy and is still good at (unwittingly) attracting ladies in spite of being completely faithful to Daisy.
79* ''ComicBook/TheFlash'': ComicBook/WallyWest, the third Flash, is probably one of the best examples of this in DC Comics. After graduating from his Kid Flash identity, Wally was characterised as being a player and constant flirt, with a large number of short-term love interests. Then in comes Linda Park; at first she's a reporter who he initially disliked, but developed into VitriolicBestBuds with, soaked in UnresolvedSexualTension. Eventually, they made it official, after which he became so devoted to her that their love was enough to overpower the pull of the Speed Force, making him both a more effective hero and showing he'd give up heaven for her. Notably, years later, Linda would seemingly be killed by the Black Flash, and later still erased from existence by Abra Kadabra, and in both scenarios, he's depicted as completely ignoring Jesse Quick (his DistaffCounterpart who had unrequited feelings for him and a healthy dose of ShipTease) because he'd loved Linda so much he'd developed SingleTargetSexuality, even when he didn't ''remember'' her.
80* ''ComicBook/GreenArrow'' and ''ComicBook/BlackCanary'' are ''both'' an example (Canary being a gender-flipped version of this). Both Oliver and Dinah are typically depicted as being fairly active daters when they're not together, and flashbacks nowadays tend to present her as being the one to make the first move while Ollie is depicted as having once been a playboy. When they're written by a writer who likes both of them, their relationship tends to be presented as loving, mutually supportive, and very dedicated, but when they're ''not'' together they tend to have no issue playing the field.
81** Oliver's former sidekick Roy Harper, former Speedy and now Arsenal, is even worse than Oliver when it comes to chasing women, to the point that, when the Titans reform and decide to nominate some new members, pretty much ''everyone'' insists on approaching their female nominees rather than risk Roy scaring them off or just asking them out and forgetting to actually ask them to join. Still, it's no question that he is still ''deeply'' hung up on Cheshire, the mother of his daughter, which has ruined any other serious relationship he's had.
82* ''ComicBook/{{Nightwing}}'' is kind of a serial example of this; despite Dick Grayson having a reputation for being a ladies' man and being arguably the biggest MrFanservice in comics, when he falls for a woman he falls ''hard''. Barbara Gordon and Koriand'r are his two biggest loves, but he and ThirdOptionLoveInterest Shawn Tsang were also explicitly ''deeply'' in love.
83* In college, ComicBook/ScottPilgrim used to be a successful casanova, with [[TheFriendNobodyLikes Julie]] warning her roommate against dating him by calling him a ladykiller to his face and providing examples. Said roommate was Envy Adams, the one who would make Scott fall for him... Making more tragic [[TheOneThatGotAway their eventual and devastating break-up]].
84* ComicBook/{{Gambit}} and ComicBook/{{Rogue}} of ''ComicBook/XMen'' are a little different than the standard -- she accepts that he has genuine feelings for her, but since her powers mean they [[CantHaveSexEver can't touch each other ever]], she wishes he'd stop pursuing her and reminding her of what she can't have. There have been some hints of the two trying therapy to get around this problem, but, [[RuleOfDrama naturally]], it hasn't worked -- "Bizarre Love Triangle" is an excellent example, where despite Emma Frost's psychic therapy sessions, an attempted make-out session nearly kills Gambit. In the late 2010s though, they finally got around this, and now the two are a HappilyMarried BattleCouple.
85[[/folder]]
86
87[[folder:Fan Works]]
88* Commander Hurricane in ''Fanfic/ABriefHistoryOfEquestria'' is historically famous for his [[ReallyGetsAround sexual]] [[TheCasanova appetite]] but fell in love with General Wind Whistler and later married Clover the Clever.
89* Piercing Gaze, the hero of ''Fanfic/ALongNightAtTheHippodrome'', is a ChivalrousPervert who can't get his mind off TheOneThatGotAway, the Great and Powerful Trixie Lulamoon. It's been almost a year since he's seen her, too.
90* ''Fanfic/PonyPOVSeries'': Thunderchild is an outrageous flirt, but acts unusually shy and chivalrous around Fluttershy.
91* ''Fanfic/{{Rules}}'': Light Yagami has had many girlfriends over the years and fully admits that, back home in Japan, he could literally have any girl he'd want, fawning over him and obeying his every whim. [[spoiler:The American Charlie, however, never falls for his charms. She constantly fights with him and infuriates him more than anyone besides Elijah/L -- and is the only girl that has ever ''connected'' with him. Light is distressed to realize that the only girl he has ever wanted might be the only girl to never want ''him'', and is rather relieved and elated when he's proven wrong]].
92* ''Fanfic/TheBlackEmperor'' has an unusual mutual example of this. [[ChivalrousPervert Lelouch]] and Milly are truly, deeply in love with each other, but that doesn't stop either of them from sleeping with other girls.
93* The ''Manga/RanmaOneHalf''/''Manga/FutabaKunChange'' story ''[[https://www.fanfiction.net/s/312018/1/Golden-Linings Golden Linings]]'' has infamous philanderer Futana finding herself falling for Ranma (currently in disguise as the girl "Yoiko Hibiki), being forced to takes things more chastely than usual for fear of Ranma's violent wrath towards perverted men. It comes to a head when Ranma's father gets attacked and needs a rare blood type that the Shimeru family happens to have. Futana realizes that this could be her way in, but [[IJustWantMyBelovedToBeHappy she can't bring herself to force anything onto Ranma]]. It does have an eventual happy if somewhat rough ending, when Ranma and Futana eventually get together, though they have to struggle with Ranma's insecurities about the idea of having sex with a guy, even if that guy is also Futana.
94* The fic ''Fanfic/HowStormerGotHerGrooveBack'' and especially its sequel involve the flirtatious rock-star Riot falling for Stormer.
95* In the ''One Piece'' fanfic ''[[Fanfic/NewGamePlusOnePiece New Game Plus]]'', Sanji is genuinely in love with Nami but refuses to act on it because he will forever flirt with everything in a skirt.
96* In ''Literature/ASongOfIceAndFire'' fanfic ''[[https://archiveofourown.org/series/968967 The Cloak of Snow]]'', ChivalrousPervert Addam Marbrand, ready to hit on any woman in sight, falls in love with Dacey Mormont. At first he is only intrigued when she rejects his advances, but after spending several weeks as JustFriends with her he realizes his feelings are less shallow this time. Dacey is attracted to him but hesitates to take new steps in their relationship, fearing he is only so interested in her because of her initial refusal.
97* [[Franchise/HarryPotter Sirius Black]] from ''Fanfic/TheBlackSheepDogSeries'' is a well-known [[TheCasanova Casanova]] who had dated pretty much every pretty girl in Hogwarts throughout his school years, then spends several years after picking up girls in bars for a one-night stand. However, he ends up falling in love with Collette Battancourt, a visiting French witch staying with his parents. He treats her with utmost courtesy and respect, to his brother's surprise and bemusement, and is offended by the notion that she's anything like his past flings.
98* ''[[https://archiveofourown.org/works/30275454/chapters/74614986 Arcadia]]'': Coco Adel is a lesbian example. She has had affairs with many women in her time, but the only girl she is genuinely in love with is her best friend Velvet. Unfortunately Coco cannot act on these affections because [[IncompatibleOrientation Velvet is straight.]] Normally this [[SituationalSexuality would not]] [[ClosetKey be a huge problem]] for Coco, except for two factors: 1. Her affection for Coco means she cannot just seduce her the way she did her past conquests and leave her when she's bored and 2. Velvet is crushing hard on [[TheHero Jaune]] [[ChickMagnet Arc.]]
99* ''Fanfic/ReturningWelshDragon'': Issei, HaremSeeker extraordinaire, ends up falling for Ritsuka to such a degree that it borders on SingleTargetSexuality - one of the tags on Questionable Questing for the story is "monogamous Issei". Especially funny once you consider that Ritsuka's number of love interests reaches memetic proportions.
100* ''Fanfic/TheStoryOfApolloDaphneAndLucaAnItalianTragedy'': [[spoiler: Resident hearthrob Vincenzo falls genuinely in love for the first time ever with Luca]].
101[[/folder]]
102
103[[folder:Films -- Animated]]
104* ''WesternAnimation/AsterixAndTheVikings'': Justforkix is apparently TheCasanova as he's hitting on the village girls during the banquet given in his honor. And his father assures that his son is used to go to "girls hunting". Yet, Justforkix will meet, then fall in love with the viking [[TheChiefsDaughter chief's daughter]] Abba, that he marries in the end.
105* ''WesternAnimation/LadyAndTheTramp'': Despite Tramp's escapades with several other dogs -- Lulu, Fifi, and Trixie, and [[OverlyLongName Rosita Chiquita Juanita]] Chihuahua -- he eventually falls for Lady.
106* ''WesternAnimation/ThePrincessAndTheFrog'': Prince Naveen makes the mistake of mentioning that he's dated ''[[ReallyGetsAround thousands of women]]'' while [[DiggingYourselfDeeper attempting]] to [[spoiler: propose to Tiana]]. A deleted scene has him discuss the trope with Ray:
107-->'''Naveen:''' I am having troubles.\
108'''Ray:''' Ya got that right, bro. You in love.\
109'''Naveen:''' I know. It is horrible!\
110'''Ray:''' But it's the good kind of horrible.\
111'''Naveen:''' I have courted many thousands of the most beautiful women in all of the world. But this girl, Tiana, she has taken my heart and... and...\
112'''Ray:''' Yeah, that's love, all right.
113* ''{{WesternAnimation/Tangled}}'': It doesn't come up in the movie itself, but [[WesternAnimation/TangledTheSeries the series]] implies that Flynn [[ReallyGetsAround Really Got Around]] before he met Rapunzel; "The Return of Strongbow" implies -- as much as a family-friendly work can imply it -- that he once had a threesome with [[TwinThreesomeFantasy a warlord's twin daughters]], and "Beyond the Corona Walls" reveals that he once left a crime boss's daughter at the altar. On top of that, he even mentions having gone on multiple dates. After falling in love with Rapunzel though, he's completely comfortable with the idea of settling down with her and no other woman could ever change his mind.
114[[/folder]]
115
116[[folder:Films -- Live-Action]]
117* Creator/AdamSandler's character in ''Film/FiftyFirstDates'' lives a life of one-night stands, then falls for an amnesiac girl who forgets each day when it's finished. Made extra ironic by the fact that this is the first girl he's ''wanted'' a real relationship with and all he can have with her is a single day at a time.
118* A plot point in ''Film/TheATeam'' movie is that Face and Lt. Sosa are former lovers. We find out later that she dumped him because he finally wanted a real relationship and she didn't.
119-->'''Face:''' You knew I was a player, and you wanted to play. Then I wanted to get serious and you couldn't handle it.
120* The '70s Australian sex comedy ''Film/AlvinPurple''. The title character is irresistible to women but falls in love with the one woman who's immune to his charms.
121* In ''Film/BlondeSavage'', Steve Blake describes himself as being the 'kiss and run type', but he falls immediately in love with "the blonde package of TNT" that is the JunglePrincess Meelah.
122* The whole plot point of the movie ''{{Film/Boomerang|1992}}'' starring Creator/EddieMurphy. He falls in love with the one woman he thinks is his equal. [[spoiler: But soon finds out that she's an even more ruthless player than he is.]]
123%%* This is the plot for the Heath Ledger version of ''Film/{{Casanova}}''.
124* ''Film/CrazyStupidLove'': Jacob is introduced as a womanizer who's only interested in one-night stands who teaches the movie's protagonist the art of seducing woman. However, over the course of the movie he falls hard for Hannah, a woman who seemingly resists his advances. At the end of the movie, they become a couple with Jacob trying to become more like the movie's protagonist Cal.
125%%* Also done in ''Film/CruelIntentions'', the modern-day adaptation of ''Literature/DangerousLiaisons''. Neither ended well.
126* Valmont from ''Film/DangerousLiaisons''. [[spoiler:However, it's arguably Deconstructed -- he continues to sleep around and ultimately leaves the woman when asked to by his partner in UnholyMatrimony. He comes to regret it and instead of making things better, he decides to get himself killed.]]
127* Subverted in ''Film/DonJon''. Jon wants to believe that this is true of his relationship with Barbara, but he really objectifies her just as much as his other sexual partners.
128* ''Film/{{Don Juan|1926}}'': Don Juan is a libertine who is so busy bedding women that he has a written schedule. But he falls in love with beautiful young Adriana and leaves his womanizing behind.
129%%* In ''Film/DonJuanDeMarco'', this is the title character's problem throughout the film.
130* Ewan [=McGregor=]'s character in the '60s rom-com pastiche ''Film/DownWithLove'' is a womanizing journalist (or "Lady's man, man's man, man-about-town") who ends up falling in love with Barbara (Renee Zellweger), the independent, modern-minded author of the eponymous [[StrawFeminist feminist manifesto]] who ''seemingly'' wants nothing to do with him.
131* Wes from ''Film/TheDuff'' was a notorious womanizer [[spoiler:until he predictably falls for his childhood friend Bianca towards the end of the film]].
132%%* Justin Long's character on ''Film/HesJustNotThatIntoYou''.
133* Averted in ''Film/{{Hitch}}'', where the eponymous character ''can'' be a [[TheCasanova [=ladykiller=]]], but he is actually very much pro-love. His job involves being the icebreaker for shy guys who want to engage in a long-term relationship. A memorable scene involves a guy who just wants Hitch's help in getting a one-night stand, so Hitch simply leaves after nearly breaking the guy's arm. Unfortunately for Hitch, his LoveInterest assumes he really does help guys get one-night stands and ends up ruining his career.
134* This happens to Film/JamesBond three times, in ''Film/OnHerMajestysSecretService'', ''Film/CasinoRoyale2006''. and ''Film/{{Spectre}}''[=/=]''Film/NoTimeToDie''. [[DownerEnding It ends badly]] in all cases. For the first two, the subsequent Bond films imply that he became a [[TheCasanova [=ladykiller=]]] (or only sought out shallow meaningless flings all the more) because he had his heart broken, which makes it happening again in the latter two all the more wrenching because he finally took a chance on a SecondLove, only for [[spoiler: HIM to die.]]
135** It's downplayed with Creator/PierceBrosnan's 007 because he wasn't given a romance that was explored as deeply as Tracy di Vicenzo or Vesper Lynd, but his character is nonetheless unique in the original continuity because he falls in love with ''two'' women (Paris Carver and Elektra King). [[spoiler:Their deaths -- the latter was even [[KillTheOnesYouLove executed by his own hand]]]] -- haunt him.
136* In ''Film/LoveAffair'', notorious playboy Michel Marnet, whose love life and women are [[WorstNewsJudgmentEver internationally famous]], falls hard for nightclub singer Terry [=McKay=].
137%%* This is the driving force behind ''Film/LoveAndOtherDrugs''.
138* ''Franchise/MarvelCinematicUniverse'':
139** In ''Film/IronMan1'', Tony Stark is a filthy rich, brilliant, narcissistic Casanova who is clearly in love with his long-time (and much beleaguered) assistant Pepper Potts - though they only start dating once he makes her CEO. While he was dying at the time and making preparations to ensure his legacy was in safe hands [[PoorCommunicationKills (and, naturally, not telling anyone about it)]] as he points out, she'd been doing the job anyway. After, the issues are less related to his playboy history, and more his inability to permanently give up being Iron Man (and his associated self-destructive streak), leading to an on-and-off romance. Even when it's off, all he does is half-heartedly hit on May Parker, and he is clearly head over heels in love. They eventually come to an accommodation over Iron Man and get married.
140** Tony's father Howard is also established to have been a playboy drawn to one-night stands in ''Film/CaptainAmericaTheFirstAvenger'' and it's spin-off series ''Series/AgentCarter'', before appearantly settling down with Maria which whom he would later have Tony.
141** In ''Film/GuardiansOfTheGalaxy2014'', Peter Quill/Star-Lord is hinted to have bedded many women previously, and his initial attempt to seduce Gamora gets him her knife to his throat. In the second movie, it's obvious that he has truly fallen in love with her. Their unofficial love theme is "Fooled Around and Fell In Love" by Elvin Bishop, all about how the singer has finally fallen in love with a woman after leaving a trail of broken hearts up to this point.
142%%* ''Film/{{Ninotchka}}''.
143* ''Franchise/PiratesOfTheCaribbean'': Jack Sparrow has undoubtedly had a lot of companions over the years. Yet he admits to having only ever loved one: [[NewOldFlame Angelica]]. This being Jack, it unsurprisingly doesn't stop him from ditching her.
144%%* Done in Creator/MartinLawrence's film, ''A Thin Line Between Love and Hate''.
145* ''Film/TheSexTrip'': Eddie normally just goes for girls that he can get into bed with quickly, and discards those girls just as quickly. When he gets to know Jess as a friend, though, he gets really attached and begins to gush about how intelligent and compassionate she is while complaining that Jess is falling for a scumbag like Matt. He even admits that Jess isn't like the girls he usually sleeps with, and admits that for once, he might be thinking about settling down into a long-term relationship -- something Steve scoffs at.
146* ''Film/TopGun'': Oh, Pete "Maverick" Mitchell. AcePilot, hotshot flyboy, and womanizer extraordinaire... who, in ''Film/TopGunMaverick'', is revealed to have been in a ''decades''-long on-again, off-again relationship with [[TheGeneralsDaughter admiral's daughter]] Penny Benjamin, with whom he is clearly head over heels in love. They go [[RidingIntoTheSunset flying into the sunset]] together in his own personal [[CoolPlane P-51 Mustang]] at the end.
147-->'''Pete''': I mean it. I'm never gonna leave you again.
148%%* The Vince Vaughn character (and to a degree the Owen Wilson character) in ''Film/WeddingCrashers''.
149[[/folder]]
150
151[[folder:Literature]]
152* Spider in ''Literature/AnansiBoys'' has godlike powers he uses to seduce women by the dozens. However, when he falls in love with Rosie while impersonating his brother Charlie, he realizes that he doesn't want to force her to love him; he wants her to love him as he is, which means admitting to her who he really is.
153* ''Literature/AnneOfGreenGables'' series:
154** Gilbert Blythe, who was wont to tease and play with the affections of the girls in his class. However, after he tries his usual tricks on Anne Shirley and gets a slate smashed over his head for his trouble, [[LoveAtFirstPunch he falls head over heels for her]]. From then on, to the other girls' massive frustration, [[SingleTargetSexuality he has eyes for no one else]].
155** Kenneth Ford, the LoveInterest of Anne and Gilbert's youngest child Rilla, is this too, though it's not as clear.
156* In ''Literature/CaptainVorpatrilsAlliance'', Ivan Vorpatril is sent by an acquaintance to pick up a girl, marries her to get cops [[spoiler:who are being manipulated by the DiscOneFinalBoss]] [[ItMakesSenseInContext off her back]], and then falls in love with her.
157* ''Literature/TheDaevabadTrilogy'' has [[MrViceGuy Muntadhir]], who ReallyGetsAround and has apparently slept with most of his social circle, falling deeply in love with honourable, straight-laced Jamshid, [[BodyguardCrush the captain of his guard]]. Causes serious problems in that the information gained during his trysts is a necessary political tool, and he's in an ArrangedMarriage to somebody ''else''.
158* Happens a lot in many literary incarnations of the Don Juan legend, the OlderThanSteam UrExample.
159* In ''Literature/FiftyShadesOfGrey'', Christian Grey starts as a successful businessman who doesn't do romance; he's only interested in dominant/submissive relationships. However, after proposing such a contract with the protagonist Anastasia Steele, he's willing to commit himself to a "vanilla relationship" with her.
160* ''Literature/FujimiOrchestra'': The gay version, with Kei, as he'd had no trouble getting men before falling for Yuuki, a man who doesn't really want him.
161%%* Sebastian in ''Literature/TheGardellaVampireChronicles''.
162* In ''Literature/GoneWithTheWind'', Scarlett takes great pleasure in flirting with any man that crosses her path, even ones who are already taken, but she has her heart set firmly on Ashley. It later turns out that the man she truly loved was [[LovingAShadow not Ashley]] but ''Rhett'' (who is also this trope towards her), but she [[LoveEpiphany realizes this]] [[BittersweetEnding a little too late]].
163* Romeo in the ''Literature/{{Hashtag}}'' book series, never hides the fact that until he met Rimmel, he was quite happy to be with any woman who showed interest. He initially tries to seduce Rimmel to win a bet and gain entry into the number one frat on campus. It's only after she lets down her walls around him and he starts to see her for who she truly is that he falls in love with her.
164* In ''Literature/HowlsMovingCastle'', Howl is a vain and [[spoiler:literally]] heartless flirt, pursuing women passionately and then losing interest after they give in. Sophie does notice when this behavior starts to change; she just totally fails to realize that she's the reason.
165%%* ''Literature/TheHungerGames'': Finnick Odair with Annie.
166* ''Literature/IsItWrongToTryToPickUpGirlsInADungeon:'' Protagonist Bell Cranel initially sought to become an adventurer in order to [[HaremSeeker win the hearts of cute girls]]... but when he gets [[RescueRomance saved by the swordsmistress]] Ains Wallenstein, he instantly forgets all about that and becomes focused exclusively on trying to win her heart alone. Ironically, not only does he fall for a girl who is ObliviousToLove, but [[UnwantedHarem a bunch of other girls start actively chasing him then]].
167* Literature/KateDaniels' love interest Curran runs into this problem when trying to court the heroine. The fact that he's had a "parade" of girlfriends doesn't help his case at all, nor does the fact that he has an ego and hates to hear the word "no".
168--> '''Kate''': And be girlfriend number twenty-three soon to be dumped in favor of girlfriend number twenty-four who has slightly bigger boobs? I don't think so.
169** Same with her best friend Andrea and her love interest Raphael.
170* HandsomeLech Sergeant Jim Chopin in the ''Literature/KateShugak'' novels. A serial philanderer, he ends up falling hard for Kate. It takes several novels for him to realise how deeply in love with her he is, and several more for him to convince her of his seriousness.
171* It's part of the initial setup for ''Literature/LastSongBeforeNight'' that the formerly womanising young musician Darien has fallen in love with young noblewoman Rianna. They're already making plans for how they'll be able to marry. Then the real plot starts and things get a lot more complicated.
172* ''[[Literature/LastHeraldMageTrilogy Magic's Price]]'' provides a QueerRomance variant when hedonistic, promiscuous young Bard Stefen falls hopelessly in love with a brooding near-celibate fellow twice his age by the name of Vanyel Ashekevron. [[spoiler: It's also ReincarnationRomance with a touch of soulmates mixed up into it.]]
173* Henry Crawford of ''Literature/MansfieldPark'' claims to be this. [[IntentionalHeartbreaker He flirts with both Bertram sisters at once without intending to marry either]], and when they leave the neighborhood he sets his sights on Fanny, who is decidedly cool towards him. He determines to make her fall in love with him because he just can't stand the thought of any woman not being so, but her continued indifference coupled with her mild good nature makes ''him'' fall for ''her'' and he's soon trying to figure out various ways to make her accept his proposal of marriage -- something he had always determined against. Unfortunately, his ego gets the better of him when he realizes Maria Bertram (now Maria Rushworth) dislikes him now... which is another challenge to overcome, and things go FromBadToWorse.
174* Marcus of ''Literature/TheMarkOfTheLion'' has a reputation as TheCasanova, but [[CuriosityCausesConversion is intrigued by]] his sister’s [[InterclassRomance slave girl]] who seems to be made of IncorruptiblePurePureness despite [[ButIWouldReallyEnjoyIt liking him too]], and eventually falls in love with her. The RelationshipUpgrade is a [[StarCrossedLovers long time in coming]], however.
175* ''Literature/MermaidMoon'': After [[ReallyGetsAround seducing countless peasant girls]], Baron Peder falls in love for the first time with protagonist Sanna. Unfortunately, his feelings aren't returned at all, and Sanna spends most of the book trying to find a way out of their ArrangedMarriage.
176* In ''Literature/TheMister'' Maxim has had ''many'' lovers though he doesn't have an emotional connection to any of them (possibly because of how his parents' marriage ended up; his mother married his father for his wealth, divorced him after getting bored and his heartbroken father died a few years later). He then finds himself genuinely falling for Alessia, which initially confuses him.
177* ''Literature/ANecklaceOfFallenStars'': Alar of "The Player and the Knave" is the local heartthrob and he genuinely falls for Tantia.
178* In ''Literature/OfFearAndFaith'', Aiden, who is known to sleep with literally every attractive woman that crosses his path, falls in love with Lilac at first sight and doesn’t know how to deal with it. He goes from shameless flirting to awkwardly distancing himself from her to genuine concern for her happiness and safety back to shameless flirting. Obviously, he CannotSpitItOut.
179* Dex is eventually this for Emma in ''Literature/OneDay'' though it takes him a fair few years and many failed relationships to realise it.
180* The first ''Literature/RedDwarf'' novel establishes that Dave Lister is perfectly comfortable with going out and seducing women as long as he's not ''too'' keen on them. When he is keen he has "the wit, charm, and self-possession of an Alsatian dog after a head-swap operation". As in the TV show, he falls in love with the out-of-his-league officer Kristine Kochanksi and promptly forgets all about any of his previous relationships.
181* ''Literature/{{Rubbernecker}}'' has a female example. Tracy is shallow and uncaring and considers an evening wasted without a quick shag. She sets out to seduce Mr Deal partly because he's attractive and partly because [[GoldDigger he's rich]]. But after they begin their relationship, she loses interest in casual sex and finds that she sometimes gets as much pleasure from sharing small moments with Mr Deal as she used to get from sex. Being with him makes her so happy that even work starts to seem almost rewarding. [[spoiler:Too bad Mr Deal is a murderer.]]
182* ''Literature/SenseAndSensibility'' has Willoughby. Near the end, he admits that his flirtation with Marianne had ''started'' as idle because he needed a wealthy wife to maintain his lifestyle, but he quickly fell as much in love with her as she was with him. His caddish ways caught up with him ''just'' as he was ready to propose when his aunt discovered that he'd seduced and abandoned their neighbor's foster daughter and subsequently disinherited him.
183* ''Literature/TheSilerianTrilogy'': Zimran, TheCasanova, falls hard for Elelar, who is [[LikeGoesWithLike very similar to him]] in terms of her sexual habits (yet with [[FemmeFataleSpy different motives]]). He wants to be committed to her, unlike all the previous women he'd been with. Zimran even fantasizes about Elelar having his baby, while before he avoided paternity like the plague, and abandoned one woman he apparently got pregnant who begged him to marry her.
184%%* Joe Morelli in the ''Literature/StephaniePlum'' series of novels.
185* ''Literature/TheStormlightArchive'': All throughout [[Literature/TheWayOfKings2010 the first book]], we see Adolin Kholin courting one woman after another (usually, though he occasionally winds up courting two or three at the same time) with an average turnover of about three days. Early in the second book, ''Literature/WordsOfRadiance'', a preliminary betrothal is formed between him and fellow protagonist Shallan Davar, and they are fairly solidly in love before the book ends.
186* Pufftail from ''Literature/{{Stray}}'' is a tomcat with likely hundreds of kittens. He's wooed many females throughout his life but spends, at most, only a few days with them before moving on and forgetting them. This all changed when he met Tammy and fell in LoveAtFirstSight with her. However, [[spoiler:Tammy died and Pufftail returned to his casanova ways to numb the pain]].
187* In ''Literature/TalesOfTheFrogPrincess'', [[FriendlyNeighborhoodVampire Prince]] [[JerkWithAHeartOfGold Garrid]], who's been described as a ladies' man, two-times [[NaiveEverygirl Li'l]] and [[AlphaBitch Princess]] [[RichBitch Hazel]] (Li'l is the more sympathetic of the two since she genuinely falls for him) by courting Hazel, but meeting Li'l, and "forgetting" to mention it. When Li'l finds out she (rightfully) leaves him. He shows up later, admitting to having fallen in love with her.
188* Kalten in the ''Literature/TheTamuli'' series by Creator/DavidEddings. Particularly funny is that he can't seem to realize the girl he likes is in love with him. Of course, what with this being a Creator/DavidEddings series, as soon as said girl finds out, she clears ''that'' right up. Expressively.
189* In ''Literature/TollTheHounds'', book eight of the ''Literature/MalazanBookOfTheFallen'', the High Priestess of Darkness is not even remotely subtle about the fact that she's interested in Spinnock Durav and He's already a regular intercourse partner due to supposedly ritualistic reasons, but Spinnock falls in love with the human priestess Salind, who seems less than thrilled about it. This doesn't keep him from trying, though. This is reinforced by the way his youth is portrayed in ''Literature/TheKharkanasTrilogy'' where he had the attention of every woman (and dragon) in sight but wasn't especially interested in any of those.
190* Adrian Ivashkov from ''Literature/VampireAcademy'' is a serial womanizer who fell hard for Rose Hathaway.
191* Mat from the ''[[Literature/TheWheelOfTime Wheel of Time]]'', he's such a ChivalrousPervert that him falling in love with [[LadyOfWar Tuon]] and marrying her was one of the signs of the apocalypse. [[NotHyperbole Literally; it's part of prophecy and everything]].
192** Don't let the marriage fool you though, he fully intends to keep drinking and gambling. His... insistence on reminding everyone of that fact is succinctly put by the [[TheStoic ever stoically]] [[DeadpanSnarker hilarious]] Talmanes:
193--> "So I believe you've told me," Talmanes said. "Three or four times so far. I half believe that if I were to peek into your tent at night, I'd find you mumbling it in your sleep. 'I'm going to keep bloody gambling! Bloody, bloody gambling and drinking! Where's my bloody drink? Anyone want to gamble for it?'"
194[[/folder]]
195
196[[folder:Live-Action TV]]
197* ''Series/{{Andor}}'' hints that the titular character feels this way about his ex-girlfriend Bix as he risks everything to get back to Ferrix to rescue her from the Empire. He's had many flings since they broke up, but he still clearly cares about her.
198* At first, Danny from ''Series/BabyDaddy'' seems like the typical hockey player who ReallyGetsAround, but backstory reveals that he's been in love with Riley since high school, even when she was still "Fat Pants".
199* ''Series/BettyEnNY'':
200** Armando is a well-known casanova, that flirted left and right with the models and other beautiful women he encountered, which he stopped after getting engaged to Marcela. However, the trope won't enter in full effect until he falls in love with Betty.
201** PlayedWith in the case of Ricardo, who was an even bigger casanova than Armando (and cared even less about feelings), and for a time he thought himself to be in love with [[spoiler: Marcela]], but the relationship went nowhere and he ended up bitter about it falling back into his old habits.
202* Happens twice with Shawn Hunter on ''Series/BoyMeetsWorld''. In Season 3, Shawn falls for a "nice girl" who doesn't want to spend all their time kissing and doesn't see him as boyfriend material. He spends the episode angsting about it until he realizes all he needed to do was listen and be honest about his feelings with her. Two seasons later he falls in love with Angela, who's also a serial dater and just as afraid of commitment and being hurt as he is. [[spoiler:Even that one didn't pan out in the end]].
203* ''Series/{{Bridgerton}}'': The leading romantic male characters of both seasons 1 and 2, Simon Basset and Anthony Bridgerton, were notorious rakes who slept around with many women before they eventually meet and fall in love with their main love interests Daphne Bridgerton and Kate Sharma.
204* Over the course of two seasons and roughly forty episodes, Rick Series/{{Castle|2009}} has fallen so hard for Kate Beckett that a) he has asked her to take care of his daughter should something happen to him, b) without hesitation, he calmly informed her that she was coming to live with him when her apartment [[spoiler:got blown up]], and c) the very ''sight'' of her kissing another man brought a look to his face that was so brokenhearted, fangirls cried. Yup, the guy's arse over teakettle, all right. For context, his EstablishingCharacterMoment was autographing a woman's chest, he's been married at least twice, and he commands a decent price in celebrity bachelor auctions.
205* ''Series/{{Cheers}}''. Sam Malone is the TropeCodifier, for five years with Diane. Even after Diane leaves, and even after his {{Flanderization}} as a sex maniac, he realizes he has Don Juan Syndrome and starts having ''friendships'' with pretty girls (namely, Rebecca).
206* Simon from ''Series/CombatHospital'' grew to have quite serious feelings for Rebecca in the first season after starting off as DrJerk TheCasanova with a GirlOfTheWeek or two.
207* Patrick, when he starts seeing Sally in later seasons of ''Series/{{Coupling}}''.
208* ''Series/Daredevil2015'':
209** Matt begins dating Karen Page partway through Season 2. It's strongly implied that Karen is the first woman that Matt has ever seriously dated since his nasty breakup with Elektra in college. Especially considering that before he found out the truth about what Matt did at night, Foggy always assumed that Matt was having lots of sexual conquests (even thinking that Matt's burner phone was for calling up girls).
210** Foggy himself is implied to be a bit of a lady's man, with a ton of one-night stands to his credit. But following Nelson & Murdock's breakup at the end of Season 2, he ends up at Hogarth Chao & Benowitz and working alongside his ex-girlfriend [[LovableAlphaBitch Marci Stahl]], who had helped Foggy and Matt with uncovering some critical information that allowed them to take down Wilson Fisk. By the time of ''The Defenders'', Foggy and Marci are back to dating full-time, and by Season 3, they're back to living together.
211* Declan of ''Series/DegrassiTheNextGeneration'', known for flirting with other girls, falls hard for Holly J, who initially rejects his advances.
212* Jack Harkness counts as this -- beginning as a character in ''Series/DoctorWho'', he was pretty much a con artist who flirted with anything. Then he gets picked up by Rose and the Doctor, falls head over heels for the latter, and ends up waiting for him to show up again for over ''one hundred years'' after they're separated. In the meantime he reworks the Torchwood Foundation from the ground up, removing a lot of the evil "in the Doctor's honour". He also gets madly flustered when trying to ask Ianto on a date in ''Series/{{Torchwood}}'' and was married at some point.
213* ''Series/{{ER}}'':
214** The {{Pilot}} establishes Doug Ross as a grade-A womanizer... who is desperately in love with Carol Hathaway. When the series wraps fifteen years later, [[EarnYourHappyEnding nothing has changed]].
215** Ray Barnett hooks up with groupies and "hot" women and claims to like them, but he proves time and again that he doesn't really care about any of them. Midway through Season 12, though, he realizes he's genuinely fallen in love with [[FromRoommatesToRomance his roommate]] Neela Rasgotra. They also eventually become an OfficialCouple.
216** Simon Brenner's first episode establishes his womanizing ways, given that [[AThreesomeIsHot he wakes up in bed with two women]], but he also falls in love with Neela. Unfortunately for him, she already chose Ray at the end of Season 13, long before he came along, and despite briefly dating, [[DidNotGetTheGirl she ultimately leaves him to reunite with Ray in Baton Rouge]].
217** Archie Morris is something of a party animal... who finds himself falling head over heels in love with police detective Claudia Diaz. While they aren't engaged by the time the series ends, Archie makes it clear that that's where he sees their relationship going, and Claudia agrees with him.
218* ''Series/{{Frasier}}'': Bulldog falls in love in the episode "Love Bites Dog" only to end up heartbroken when the woman dumps him on the phone as he himself does with many of his one-night stands.
219** A few years later, Bulldog falls for Roz who also rejects him.
220* Joey on ''Series/{{Friends}}'' had a brief thing for Rachel. However, it really started back when the girls practically threw one of his girls of the week at him and he realized what the rewards of a relationship could be.
221* Santana from ''Series/{{Glee}}''. After a lot of sleeping around, including with Brittany, she realizes that Brittany is all she really wants.
222** In "Duets", Artie breaks off his pairing with Brittany when he thinks she seduced him just so he would sing with her. Turns out her affection was genuine after all.
223** Noah "Puck" Puckerman, having dated Quinn, Rachel, Mercedes, Santana, and half the Cougars in Lima, finds himself falling head over heels, to the point of joining Celibacy Club because he wants to be less of an "I'm a Man I can't help it" type guy, for Lauren Zizes, President of the AV club and only girl on the school's wrestling team, because she's as much of a badass as him. She initially, despite being attracted to him, tells him they'll have to be JustFriends at first because "she needs to be wooed." And Puck -- who formerly couldn't even get through an evening with Quinn without sexting Santana -- is okay with this arrangement. In short -- we have one Casanova who's found a love match!
224* A RareFemaleExample in ''Series/GoodWitch.'' Abigail can almost always wrap a guy around her finger with little to no trouble, so she gets incredibly nervous when she actually starts falling for one in earnest. Cassie gently lampshades this trope.
225* Happened to Chuck on ''Series/GossipGirl'', who fell in love with Blair. When she denied him he found himself unable to perform with other women (thus deciding to use her as "sexual Drano" which didn't go so well). He bounced back and started sleeping around again until he and Blair actually became a couple.
226* Alex Karev of ''Series/GreysAnatomy'' is a contender for the long-term record. After eight seasons of bedding a different girl literally every week, he resolves to become a responsible, homeowner, resident doctor-type and stop seducing his interns. He promptly gets his heart broken by the next intern, who wants to be best buddies only.
227* ''Series/{{Hightown}}'': Jackie starts out as a [[TheCasanova lesbian casanova]] in Season 1. During Season 2 though she gets into a committed relationship with Leslie, though it doesn't last.
228* Brendan Brady prides himself on not getting too invested in his conquests, but that all changes when he falls hard in love with Ste Hay on ''Series/{{Hollyoaks}}''.
229* Barney Stinson, quoted above from ''Series/HowIMetYourMother''. Sort of a subversion since he doesn't tone down his promiscuity at all (although he tries) for the sake of his newfound love (at least until they actually [[DeconfirmedBachelor get together)]].
230* In ''Series/KamenRiderKiva'', Otoya falls in love with Yuri. However, he ultimately falls in love with Maya, and Yuri ends up marrying another man off-screen.
231* The titular character of ''Series/{{Lucifer|2016}}'' is shown to have multiple flings (with men and women) over the course of the show. This changes when he falls in love with Detective Chloe Decker, described in the episode "Who's da New King of Hell?" [[spoiler:as the Devil’s first love]].
232* Shane from ''Series/TheLWord''. Multiple times, as it never lasts.
233* Don Draper from ''Series/MadMen'' in the Season 4 finale and all of Season 5.
234* Though not part of the main storyline, this is the story of [[BumblingDad Hal]] and [[MyBelovedSmother Lois]] in ''Series/MalcolmInTheMiddle''. It's really one of the most adorable things: it has been established that Hal was a HUGE player before meeting Lois, and yet afterwards he is so completely in love with and devoted to her that Lois actually feels guilty because she's unable to love him as much as he loves her... and he tells her if she loved him as much as he loved her, they would never leave the bedroom. Though it has led to the UnfortunateImplications that due to his complete devotion to her, erratic personality changes when she is gone for a long period of time, and that he was dating Lois' sister before meeting her that she brainwashed him.
235* Phryne Fisher of ''Series/MissFishersMurderMysteries'' has quite happily shagged her way across several continents, but after an [[DomesticAbuse abusive relationship]] had no intention of falling in love with anyone ever again until she met stoic, quietly snarky, morally upright Detective Inspector Jack Robinson, who quietly won her heart almost before she even knew he was doing it.
236* In Season 4 of ''Series/{{NCIS}}'', Tony [=DiNozzo=] finds himself in this position with Jeanne Benoit, with the added complication that [[spoiler:he initiated the relationship as part of an undercover operation and was never supposed to actually fall in love with her]].
237* Done in the GrandFinale of ''Series/NightCourt'', where Dan vows to give up his KavorkaMan ways and earnestly pursue his dream woman, Christine. (It should be noted that Dan confesses this to Harry, not Christine.) While they don't get together, the revival reveals that he did end up genuinely HappilyMarried to another woman and is still in mourning several years after her death.
238* Similar to the above example, Ricky of ''Series/NoahsArc'' once he falls in love with Junito (he considers breaking his promiscuous ways, but it never pans out for long).
239* In the Japanese drama ''Series/NodameCantabile'', DirtyOldMan Stresemann had fallen in love with the school's principal when they were younger. But they decided to remain JustFriends after she was struck with an illness that stopped her from playing piano. Years later, visiting her and coming to the academy as a guest instructor, he chose to conduct her favourite song before he left Japan. His feelings for her had never changed.
240* Don Eppes of ''Series/{{NUMB3RS}}'' becomes this when he falls in love with Robin. Though the "Ladykiller" part is more of an InformedAttribute than anything.
241* Nathan on ''Series/OneTreeHill'' started as a JerkJock who'd do anyone. Then he fell in love with Haley, so in love that he not only reformed his ways but he married her in high school. Years later they're still married.
242* One episode of ''Series/{{Psych}}'' features Clive Prescott, a self-proclaimed "cad and deceiver" who has written books and teaches a class on the subject of ladykilling. He's believed to be romancing a rich widow to gain access to her money, until he reveals that he's romancing her because, to everyone's surprise, not the least ''his own'', he has genuinely fallen in love with her.
243* Inverted by ''Series/QuantumLeap''. It's established early on that Al is a ChivalrousPervert who eyes any woman he sees and has been married multiple times. Then in the episode "M.I.A.", he outright admits that his first wife Beth[[note]]Who he "lost" because he was a POW for four years and she remarried in the meantime[[/note]] was the only woman he ever truly loved, and that he chases skirt in the hopes of finding someone who can mean as much to him. [[spoiler:In the final episode Sam uses his "one free leap" to tell Beth not to give up on Al, which she does, and the closing text tells us that they're still HappilyMarried in 1999 and have had four daughters.]]
244* Titus Pullo from ''Series/{{Rome}}'' is a ChivalrousPervert who sleeps with anything that moves, yet falls hard for the beautiful slave girl Eirene, even going so far as to free her so he can marry her. [[spoiler: Sadly, it [[MurderTheHypotenuse doesn't]] [[KillTheCutie end well]] for the poor girl.]]
245* Parodied on ''Series/SaturdayNightLive'' (of course) in a Ladies Man sketch in which Leon announces that he is in love and off the market. It turns out that his dream woman is an undercover cop... played by The Rock... who is, even in-universe, very and obviously male (much to Leon's obliviousness).
246** Played straight in TheMovie where Leon falls for a woman and ends the story married with a child, but still doing his radio show.
247* Lee Stetson/Scarecrow of ''Series/ScarecrowAndMrsKing'' gradually abandons his womanizing ways over the course of the series as he falls for (and eventually marries) Amanda King.
248* ''Series/{{Seinfeld}}'''s Kramer, generally confident in his ability to charm any woman, falls ''hard'' for Jerry's GirlOfTheWeek in the episode "The Soul Mate," becoming so tongue-tied around her that he has to recruit Newman to hide behind a shelf at the bookstore where she's working and feed him lines.
249* Samantha on ''Series/SexAndTheCity'' has fallen in love a few times over the series run. In the first season, it was with James but she was dismayed when he had [[TeenyWeenie a really small penis]]; second time was with Richard who she finds herself actually wanting a monogamous relationship with (she complains to her friends "I think I caught monogamy! I must've gotten it from YOU people!"); and finally with Smith who broke through more of her emotional barriers than any other guy she fell in love with.
250* ''[[Series/TheSuiteLifeOfZackAndCody The Suite Life on Deck]]'' has a {{Kidanova}} example in Zack Martin, who early in Season 3 fell head-over-heels for the new girl Maya, and vowed to reform his womanizing ways for her sake.
251* A Season 1 episode of ''Series/{{Supernatural}}'' introduces us to [[TheCasanova Dean]] [[TheCharmer Winchester's]] NewOldFlame Cassie. We get a glimpse of what Dean looks like in love, and it turns out he's kind of a sap. Sam has fun needling him about it until he realizes who dumped whom and why, and how badly [[TheWoobie Dean]] actually got hurt.
252* ''Series/{{Thanks}}'': Burnaby is a world-traveling merchant who's been with countless women. When he meets Grammy, he wants to settle down with her.
253* [[MagnificentBastard Steven Hyde]] of ''Series/That70sShow'' when he falls in love with [[{{Tsundere}} Jackie Burkhart]]. Prior to this he had been sleeping around and was proud of never having formed any real attachments (even when he ''did'' have a thing for Donna). They maintain the relationship throughout several seasons, despite many setbacks involving Jackie's ex (and Hyde's best friend) Michael Kelso, and even [[BelligerentSexualTension break up several times]] due to Jackie's desire to get married one day. They finally find a resolution when [[spoiler:Jackie is offered a job in Chicago, so she gives Hyde an ultimatum to propose or she will leave. He initially says no, so she leaves for Chicago, but Hyde follows her, another example of his actually being in love with her. When he gets there he finds Kelso already there with her and dressed only in a towel. This ends their relationship and Hyde goes back to sleeping around]].
254* Jack of ''Series/ThreesCompany'' never fails to show up with a GirlOfTheWeek, until the series finale where he's shown to settle down with his newest girlfriend Vicky. His friend Larry was also shown to seriously consider marrying one of his Girls Of The Week in one episode until Jack successfully talked him out of it (after discovering that said girl was actually a StalkerWithACrush for ''him'').
255* Owen Harper of ''Series/{{Torchwood}}'', the series' KavorkaMan, falls for a 1950s aviatrix who slips through a rift in time and, after a week-long affair and Owen's stumbling confession of love, flies right back through the rift and out of his life.
256* ''Series/{{Trace}}'': In "Don Juan's Daughter-in-Law", after sleeping with dozens of women over many years, Artyom falls really in love for the first time. Unfortunately, [[spoiler:the woman is much younger than him and very impulsive and he realizes she might come to regret their relationship]]. Even more unfortunately, [[spoiler:she is engaged to his son]]. He attempts to BreakHerHeartToSaveHer, and, when that fails, [[ScrewThisImOuttaHere plans to move to another city several thousand miles away]]. [[spoiler:However, before he can do so, his son catches them together and [[{{Patricide}} murders him]]]].
257* ''Series/{{Turn}}'' plays this trope for drama and tragedy with [[TheCasanova Major]] [[TheChessmaster John]] [[ManipulativeBastard Andre]], the head of British military intelligence. He likes to use his charm and good looks (as well as sexual liaisons) to turn women into agents and sources, and that's what he plans to do with gorgeous young [[WorldsMostBeautifulWoman Peggy Shippen]] in Philadelphia -- he convinces her to begin communicating with Benedict Arnold in order to turn him to the British side. However, Andre falls in love with Peggy and plans to elope with her in New York, until he realizes that leaving her in rebel-occupied Philadelphia would help his cause. Unfortunately, Peggy eventually marries Arnold, while Andre obsesses over turning Arnold in order to get her back. This leads to his getting caught behind enemy lines and being hanged as a spy.
258* Daniel on ''Series/UglyBetty'', at least once a season.
259** Also Armando Mendoza, his equivalent in the original ''Series/YoSoyBettyLaFea''.
260* Damon Salvatore with Elena/used to be Katherine in ''Series/TheVampireDiaries''.
261* ''Series/{{Velvet}}'': Mateo works to give up his ladykiller ways once he genuinely falls for Clara. His difficulty adjusting to monogamy partially fuels the SlapSlapKiss nature of their relationship.
262* ''Series/VeronicaMars'': Logan Echolls, who ReallyGetsAround, refers to most of his conquests as "playmates" or a variation thereof -- but admits to genuinely loving [[PosthumousCharacter Lilly Kane]] and [[SecondLove Veronica Mars]] (and, with the latter, manages to not even slightly fall into adulterous behaviour).
263* Kojo in ''Series/ZekeAndLuther'' developed feelings for Zeke's cousin Mia in the episode "Sludge".
264* Logan Reese, from ''Series/{{Zoey 101}}'' seems to act like this after he starts dating Quinn, as he is not shown flirting with other girls after their FirstKiss.
265[[/folder]]
266
267[[folder:Manhua]]
268* Invoked in ''Manhua/GoddessCreationSystem''. Xiaxi knows that Mingyi bores of anything he obtains easily, so she deliberately resists his advances. Not used to having women not fall to his charms, he pays more and more attention to her and becomes fixated on winning her over until he eventually falls in love.
269[[/folder]]
270
271[[folder:Music]]
272* ''Assassin'' by John Mayer is about a ladykiller who falls for one of his many conquests. Unfortunately for him, she is only interested in a one-night stand. "I was a killer was the best they've ever seen. I'd steal your heart before you ever heard a thing... LittleDidIKnow that girl was an assassin too."
273* A musical example would be "Conquest" by Patti Page (later covered by the White Stripes).
274* Music/{{Mecano}}'s song ''La fuerza del destino'' ("The strength of Fate") depicts how a Casanova is at first peeved that his date denied him a kiss on the first date, but as time passes he comes to develop feelings for her.
275* "Fooled Around And Fell In Love" by Elvin Bishop, used to a tee for the aforementioned ''[[Film/GuardiansOfTheGalaxy2014 Guardians of the Galaxy]]''.
276* ''Stealing My Heart'' by Music/{{The Rolling Stones|Band}} is all about this, containing lyrics like: "I was just out there to have me some fun / but it's easier said than done," and "I thought you were dinner, but you were the shark."
277* A common interpretation of Ryuusei-P's [[Music/{{Vocaloid}} Kagamine Len]] song "Spice!". The song itself declares that the singer sleeps around because he's scared of approaching emotional vulnerability and intimacy, but a few notable [=PVs=] have it so Len falls in love with one of his lays and doesn't know how to handle his feelings.
278* Music/RoxyMusic's songs often fall into this trope.
279* Brooks & Dunn's "Brand New Man"
280* Gender-inverted with Music/TheGoGos' (being an all-female band) "Lust to Love".
281* Gender-inverted with "Maneater" by Blue Eyed Blondes. It... [[ImAHumanitarian doesn't]] [[{{Yandere}} end]] [[AxCrazy well]].
282* [[https://youtu.be/2ghj8_DpDfU Brains Out]] by Kim Cesarion is about a promiscuous man who falls for a woman.
283* The ''Music/StudioKillers'' song "Grand Finale" is about a woman in this situation after she falls in love with another woman:
284-->I've been a dirty bastard but I will clean my act up.
285-->I wanna stop doing bad.
286-->I wanna meet your mom and dad.
287* The Marshall Tucker Band's "Heard It In A Love Song".
288* Defied and gender-inverted in "This Woman" by K.T. Oslin in which the protagonist is [[EthicalSlut a playgirl who's letting a guy know]] that she's not into long-term monogamous relationships:
289-->This woman's in love with you baby
290-->This woman don't think you can do no wrong
291-->But I think it's only fair to warn you
292-->This woman don't stay in love for long
293* ''Music/ConfessionExecutiveCommitteeLoveSeries''' "Mean Encounter" covers the school playboy, Ken Shibasaki, meeting the one girl in school who won't give him the satisfaction of dating her. Through his attempts to win her over, he genuinely falls in love, only to set himself up for failure when he breaks off engagements with other girls. Though it's implied he's liked her for a long time, given that he looked out for her from afar in middle school ("Assertion of the Heart").
294* Hunters and Collectors' "Ladykiller" is about a ladykiller who desperately wishes to be a ladykiller in love
295* Billy Ocean's "Red Light Spells Danger" is about a ladykiller who always hoped to defy this trope but is starting to notice the danger signs.
296* Music/DemiLovato's "Heart Attack" is a GenderInvertedTrope example.
297--> When I don't care I can play 'em like a Ken doll
298-->Won't wash my hair, then make 'em bounce like a basketball
299-->But you make me wanna act like a girl
300-->Paint my nails and wear high heels
301-->Yes, you make me so nervous that I just can't hold your hand
302[[/folder]]
303
304[[folder:New Media]]
305* Liam of ''Website/GaiaOnline'' eventually develops real feelings for Sam, as opposed to meaningless flirting.
306[[/folder]]
307
308[[folder:Newspaper Comics]]
309* Lois on ''ComicStrip/DykesToWatchOutFor'' falls ''hard'' for Emma, and eventually enters into an uneasy triad relationship with her, but eventually tires of playing second fiddle to Emma's primary partner Dorothy.
310[[/folder]]
311
312[[folder:Theatre]]
313* In ''Theatre/CactusFlower'', after one year with Toni, Julian realizes that he no longer enjoys his old habit of taking "a different girl every night," much as he's tried to fight his feelings for her by dating other women. Having known at first sight that he could get too emotionally involved with her, he lied to her that he already had a wife and three children, but that didn't prevent her from developing strong feelings for him.
314* Sky Masterson in ''Theatre/GuysAndDolls'' after he takes Miss Sarah Brown to Havana. He initially claims "if I wish to take a doll with me to Havana, there is a large assortment available."
315* In ''Theatre/TheHunchbackOfNotreDame'', both Phoebus and Jehan are this towards, respectively, Esmeralda and Florika, as part of Jehan's AdaptationalHeroism.
316* ''Theatre/{{Hamilton}}'': Both Alexander Hamilton and Aaron Burr, in one of the few things they have in common, are both "reliable with the ladies", and Hamilton explicitly was so infamous that Martha Washington named her tomcat after him ("[[TruthInTelevision It's true!]]"), but both men end up falling deeply in love, Hamilton with Eliza Schuyler, Burr with a woman named Theodosia, who dies offscreen, and rather than move on, Burr apparently focuses on raising his daughter, whom he named after her. Somewhat deconstructing this trope, though Hamilton and Eliza remain HappilyMarried at first, his workaholic nature means they spend much time separated, and he ends up cheating on her, never mind the heavily implied attraction he had to her sister Angelica.
317* Harold Hill in ''Theatre/TheMusicMan'' finds himself too attached to Marian to make the timely getaway from River City he had originally planned.
318-->"For the first time, I got my foot caught in the door."
319* Maureen from ''Theatre/{{Rent}}'' is a female, bisexual example. She'll sleep with ''anyone'', but has strong feelings for Joanne.
320* Fiyero from ''Theatre/{{Wicked}}'' is a handsome and charming prince who can (and does) have any girl he wants in the palm of his hand -- any girl...except Elphaba. Guess who he ends up falling genuinely and deeply in love with.
321* Valentine in Creator/GeorgeBernardShaw's ''You Never Can Tell'' is a particularly meta example: a Ladykiller whose shtick is to ''pretend'' to be a Ladykiller In Love, who for the first time falls genuinely in love. Once Gloria learns that all his protestations of love are rehearsed lines, it becomes especially hard for him to convince her that this time, he means them.
322[[/folder]]
323
324[[folder:Video Games]]
325* Vico's romance arc in ''VideoGame/ADanceWithRogues''. Also possibly gender-flipped with the player character.
326* Deconstructed by [[VampiresAreSexGods Astarion's]] romance in ''VideoGame/BaldursGateIII''. He depicts himself early on as a frivolous player who will pretty much make a pass at every single person at camp, including the player, who he flirts with shamelessly on pretty much every occasion. If romanced, however, he'll actually reveal in his Act 2 LoveConfession that [[spoiler:he'd been falling back on his past instincts as a seductive lure for his [[IHateYouVampireDad abusive master Cazador]] and purposely seducing them in order to gain their loyalty and protection. He'll admit that his "plan" quickly fell apart when he fell in love with them for real, and he began to feel guilty in continuing the relationship without them knowing his original intentions.]]
327* Part of the backstory of The Rogue, Lyndon, in ''VideoGame/DiabloIII''. Exactly how much SUCCESS he has with women is anybody's guess, but he's definitely eager to flirt with anything in a skirt... or a FurBikini... or a skimpy mage-robe... he's not picky, really, and doesn't even wince at being shot down. If you chastise him for his womanizing, he claims that he's only ever met one woman 'worth keeping'. Further digging into his past reveals that he originally [[StartOfDarkness turned to crime]] in order to fund his attempts to woo her and that she was so displeased that she ended up marrying his NiceGuy [[DifferentAsNightAndDay brother]] instead. The pain in his voice is audible whenever she comes up in conversation, turning his otherwise LoveableRogue demeanor bitter in a split second...
328* A possible outcome in ''VideoGame/DragonAgeOrigins'' for the DepravedBisexual elf Zevran, if the PC (male or female) can get Zevran's approval meter high enough. Zevran gets it so bad, in fact, that should [[spoiler:[[HeroicSacrifice the Warden perish]] during the FinalBattle]], Zevran is unable to love anyone ever again in his life.
329** Isabela, the sexy pirate queen you can recruit for a threesome in ''[[VideoGame/DragonAgeOrigins Origins]]'', has much deeper feelings for Hawke in ''VideoGame/DragonAgeII'' than she's initially willing to let on. Likewise, Anders--who flirts with more or less everybody in ''Awakening'' -- gets dead serious for Hawke ([[SanitySlippage though he also just]] [[WellIntentionedExtremist gets dead serious in general]]).
330* In ''VideoGame/EnsembleStars'', Kaoru starts off as a flirt who decided to become an idol solely so he'd be able to meet a lot of girls, and is excited to meet the AudienceSurrogate just because it'd be nice to have a girl to flirt with at school amongst [[OneGenderSchool all the guys]]. By the end of the year, he's one of the few characters to have explicitly and clearly fallen in love with her and ultimately promises to meet up with her again someday and win her over properly.
331* ''VideoGame/FarCry3'' has Dennis Rogers, a Liberian man welcomed into the [[ProudWarriorRace Rakyat tribe]] who [[MagicalNegro serves as a mentor to Jason Brody]]. Dennis apparently was a womanizer before joining the Rakyat, and he proudly shows some of the native women to Jason, saying that he could have any one of them if he felt like it, but his heart is set on Citra, the JunglePrincess and leader of the Rakyat. [[spoiler:Sadly, Citra is more interested in [[MightyWhitey Jason]] than him, and as the game goes on, Dennis becomes increasingly jealous. Eventually, if you pick the "Save Your Friends" ending, and have Jason refuse to kill his friends and cut all ties with the outside world, Dennis furiously tries stabbing him to death, only for Citra to shield Jason [[TakingTheBullet at the cost of her life]]. Dennis has a MyGodWhatHaveIDone reaction. According to game director Jeffrey Yohalem, when asked about Dennis' fate after that ending, "Dennis is a hardcore gamer. He'll find another game."]]
332* Zidane Tribal, the protagonist of ''VideoGame/FinalFantasyIX'', has this as a major part of his CharacterDevelopment. He starts out as a fairly open skirt chaser (at the age of [[ArtisticAge 16]], no less), but then he falls for Garnet/Dagger, causing some emo-ness to ensue. Of course, in his case, it's made worse by the fact that Garnet's a princess, therefore supposedly not "reachable" for him even if he changes his ways. [[spoiler: Doesn't stop them from getting together in the end, though.]]
333* ''Franchise/FireEmblem'':
334** Sain in ''VideoGame/FireEmblemTheBlazingBlade'' is a [[ChivalrousPervert known flirt]] who usually shakes off women's rejection with a sad sigh and a [[DoggedNiceGuy continued effort to win them over]]. But in his supports with WhiteMagicianGirl [[TheOjou Priscilla]], when she gently tells him that [[StarCrossedLovers a relationship between them wouldn't work out]] [[UptownGirl due to social status and location]], he seems genuinely crushed by the revelation and even breaks down crying for his "Princess".
335*** In a variation, his supports with his [[BashBrothers best friend and long-time partner]] [[SugarAndIcePersonality Kent]] show that he also may have feelings for their common lady of liege, Lyndis. However, he realizes that [[LoveTriangle Kent also]] [[BodyguardCrush is in love with Lyn]] ''and'' his feelings might be deeper than Sain's own, so [[MatchmakerCrush decides to support a relationship between them instead of pursuing Lyndis himself]].
336*** It's not only with Priscilla, either. His supports with Fiora have him [[DeclarationOfProtection trying to protect her]] [[SickEpisode despite being afflicted with a severe fever]], and she takes care of him despite not having really believed his claims. If they reach the max support level, they get married.
337** In ''VideoGame/FireEmblemGenealogyOfTheHolyWar'', Alec is another ChivalrousPervert who is pretty flirty towards the ladies in Sigurd's army. When he ''is'' paired up, though, he becomes quite loyal to [[BattleCouple his lover and partner]].
338** In ''VideoGame/FireEmblemAwakening'', Virion is a ChivalrousPervert who is ''heavily implied'' to sleep around with either maids or noblewomen in his supports with his NinjaMaid Cherche, but he fits in here if he's romanced by any of the girls.
339*** Played with in regards to Inigo [[spoiler: who can be potentially fathered by Virion]]. He's a HandsomeLech and flirts around quite a bit in canon [[RunningGag and gets turned down every time]], so when he pledges his affection to the girls, they tend to not believe him. (And sometimes he doesn't help his own case). He ''does'' seem to fully mean it [[TimeTravelRomance if romanced by the female Avatar]], though:
340---->“I used to say this to all the ladies, but you're truly the only one for me.”
341*** Also implied in regards to Gaius. [[spoiler: Who ''also'' can be the dad of Inigo]]
342---->"You're not the first to fall for me, but you're the only one I've cared about back."
343** ''VideoGame/FireEmblemFates'' has Laslow, an Inigo {{expy}} who just like the original, flirts around quite a bit and is turned down either on-screen or off-screen, but when he falls in love he ''does'' stay loyal to his wife, who sometimes will not believe him when he gives her a LoveConfession. [[spoiler: Completely justified: Laslow isn't an Inigo {{expy}}... he actually '''is''' an OlderAndWiser Inigo]]. Funnily enough, this will become a double example if he's paired with [[GoldDigger Charlotte]] and the two will agree to an open relationship.
344** The tradition is continued in ''VideoGame/FireEmblemThreeHouses'' with Sylvain, who's notorious for chasing anything in a skirt (to the point a female [[PlayerCharacter Byleth]] can make him switch Houses with no struggle at all). All four of his endings paired with women have elements of this, [[spoiler:but it's actually a subversion. Sylvain holds the women he flirts with in contempt because they're all [[GoldDigger after his Crest and noble lineage]]. In order for him to fall in love, a woman has to see through the ladykiller act and relate to him properly, not just flirt. Once he falls for a girl who does this, there's no indication he's anything but completely faithful.]]
345* ''VideoGame/HarvestMoonDS Cute'': If you choose to go for Skye, a playboy thief. His lines get cheesier with each heart event.
346* ''VideoGame/NeverwinterNights2'': Mask of the Betrayer has Gannayev, an abnormally handsome hagspawn Casanova. As you get to know him better, it is revealed that he is unsatisfied with such an existence and is actually looking for "a dream that truly touched" him. Moreover, his cocky over-the-top attitude, as well as the Casanova ways, are a shield he puts up to mask his inner insecurity and fear of showing people who he really is. Needless to say, given the right treatment he strips away his pretensions and adapts a worshipping lovebird attitude toward the protagonist.
347* Daeran from ''VideoGame/PathfinderWrathOfTheRighteous'' is a spoiled, sarcastic hedonist who will sleep with practically anything or anyone, if only once for the novelty, and his romance begins out as him seducing you partially for the fun of the chase (and because dating TheChosenOne will annoy his cousin, the queen of Mendev). Stick with him past the halfpoint of the game and especially during chapter 4 and he will begin to catch actual feelings for the Knight-Commander, [[spoiler:which is a huge problem for him because the EldritchAbomination that is [[DemonicPossession possessing him]] has a tendency of [[HeKnowsTooMuch tearing the heads off anyone who it suspects knows of its existence, which includes anyone who gets close enough to Daeran to actually care for him as a person]]. Consequently Daeran will resist any attempt to get closer to him unless you're able to help him with his possession]]. Even before then, thanks to EvenEvilHasStandards, he considers it below him to cheat or double-time (he is accepting of {{Polyamory}}, but he is also the only LoveInterest to do so so it's a moot point anyway) and will remain faithful to the Knight-Commander if romanced. [[spoiler:If the Knight-Commander sacrifices themselves to seal the Worldwound, the WhereAreTheyNow epilogue for a romanced Daeran reveals he mourned them for the rest of his life.]]
348* Ryoji Mochizuki from ''VideoGame/Persona3'' if you pursue a romantic relationship with him. Despite the fact he's a constant flirt, he tells the female protagonist that she's the only girl he's ever loved after his S link is maxed.
349* Pretty much the whole deal behind [[ChivalrousPervert Yuushi]] [[TallDarkAndHandsome Oshitari's]] paths in ''Manga/ThePrinceOfTennis'' {{Dating Sim}}s. Especially in ''Gakuensai no Oujisama'', where the main girl Shizuka even gets to see him get bitchslapped by an old girlfriend.
350* In ''VideoGame/StarWarsTheOldRepublic'', this is a possible outcome of Doc's romance arc with a female Jedi Knight.
351** Played with for Andronikos Revel's romance with a female Sith Inquisitor. (While he's not a ladykiller per se, Andronikos does have a long string of short-lived relationships behind him due to his CommitmentIssues. If things progress well enough, he eventually overcomes these to remain with the female Sith Inquisitor.
352* ''VideoGame/TeamFortress2'': Most of this plays out in the supplementary materials and {{Fanon}}, but it's pretty heavily implied that the relationship between the RED Spy and the BLU Scout's mother is this trope (his rival, BLU Spy, took a bunch of pictures of them on a date and then having steamy sex with each other, but the RED Spy only claimed one of them back for himself: the one showing him and his "petit cho-fleur" holding hands).
353** as of [[http://www.teamfortress.com/tf03_cold_day_in_hell/ A Cold Day In Hell,]] [[spoiler: [[http://www.teamfortress.com/tf03_cold_day_in_hell/#f=55 Scout ]] [[http://www.teamfortress.com/tf03_cold_day_in_hell/#f=56 towards ]] [[http://www.teamfortress.com/tf03_cold_day_in_hell/#f=59 Miss Pauling ]] ]]
354[[/folder]]
355
356[[folder:Visual Novels]]
357%%* In ''VisualNovel/DoubleHomework'', if the player makes at least reasonable decisions, the protagonist becomes this by the end of the story.
358* Koujaku from ''VisualNovel/DramaticalMurder'' is known to be TheCharmer who has a tendency to sleep with many different women, much to Aoba's annoyance. Taking Koujaku's route reveals he's always had feelings for Aoba since [[ChildhoodFriendRomance they were children]], and Koujaku stops picking up other women completely in his good ending.
359* Heo Ae-Jeong from ''VisualNovel/HatePlus'' was a famous actress who would regularly take female fans of hers to bed, eventually moving on to the next one. She was in all likelihood planning the same with Mae Jin-a, a bubbly and cute florist, when Jin-a revealed a subtle wit when calling out Ae-Jeong's costar for putting her down, and Ae-Jeong fell in love. [[spoiler:Unfortunately, due to increasingly restrictive laws and societal opinions, Ae-Jeong felt obligated to become the concubine of a wealthy man from the Ryu family in order to secure her future. When Jin-a objected and seemed unable to move on, Ae-Jeong suddenly dumped her, coldly claiming she never really loved her in the first place. Jin-a presumably got married off after that, becoming very bitter towards Ae-Jeong. However, in a conversation with an unrelated person, Ae-Jeong referred to the hairpin Jin-a gave her as being given to her by her "first love", indicating that she ''did'' have genuine feelings for Jin-a, and it's heavily implied Ae-Jeong managed to convince Ryu to shelter Jin-a with her at some point between the failed rebellion and the coronation of Emperor Taijo by pretending that Jin-a was her little sister.]]
360* Tara Bryck from ''VisualNovel/HeartOfTheWoods'' has hooked up with many girls in the past (many of them fans of hers) and ends up doing the same with Morgan, but over the course of the game, it becomes increasingly clear that she's in denial of the fact that she's genuinely falling for her.
361* ''VisualNovel/IkemenSengoku'':
362** Hideyoshi has numerous fangirls and past lovers, but on his route, he realizes that his feelings for the main character run deeper than any relationship he's had with another woman in the past.
363** Shingen has reportedly never failed to seduce a woman in the four years Sasuke's known him, but he's always kept things casual with other women because of [[spoiler:him slowly dying of an illness]] until he finds himself opening up to the main character in a way that he's never done with anyone else.
364* Derek in ''VisualNovel/REAlistair'', if you get his ending. He gets bonus points for [[spoiler:initially flirting with Merui solely to play with and emotionally string her along, only to admit [[BecomingTheMask developing genuine feelings for her]] when she confronts him about this]].
365* ''VisualNovel/StarryFlowers'': The [[ReallyGetsAround notoriously thirsty]] Periwinkle finds himself growing more attached to Pastille than to any of his previous dates, to the point where he becomes unable to enjoy casual relationships with anyone else anymore.
366[[/folder]]
367
368[[folder:Web Animation]]
369* A one-shot character in ''Animation/{{Pucca}}'' is rich, famous, handsome, and has all the Sooga ladies falling for him. He goes after the title character, who is already obsessively in love with Garu. As it always does for anyone getting in Pucca's way of Garu, it does not end well for the ladykiller.
370[[/folder]]
371
372[[folder:Webcomics]]
373* The protagonist of ''[[Webcomic/Alfie2010 Alfie (2010)]]'' is a downplayed example. She has few notches on her proverbial bedpost; but she has solidly internalized the belief that romantic commitment is shorthand for heartbreak, bitterness, and[=/=]or hypocrisy while growing quite comfortable indulging in mutually enjoyable casual romps with her friends. As a few scratched-out entries in her journal indicate, she is rapidly developing deeper feelings for Ozge than "like" or "regard as hot" and is not comfortable about them at ''all''.
374* Gannet from ''Webcomic/{{Avialae}}'' viewed love and relationships as too messy to deal with due to seeing his parents and uncle's relationships fall apart and was content to just sleep around as much as possible. Until he met Bailey and realized that he wanted to do the actual work of maintaining a relationship for the first time in his life.
375* Fox from ''Webcomic/BoyMeetsBoy'' and ''Webcomic/FriendlyHostility'' flirts with everyone until he develops a serious interest in his best friend Collin. Collin, fully aware of Fox's lecherous nature, initially refuses to play into his "game" until Fox bluntly tells him, "I'm not kidding around anymore, Collin." The two wind up in a stable and loving relationship that lasts for years, and Fox [[spoiler:is genuinely heartbroken when Collin eventually breaks up with him]].
376* The eponymous [[ManicPixieDreamGirl Roomie]] of ''Webcomic/GoGetARoomie'' doesn't mean to be a ladykiller -- she maintains that she loves everybody equally and is dismayed whenever her FriendsWithBenefits inevitably fall for her. And then Roomie meets Lillian, who fits [[ILoveYouBecauseICantControlYou basically]] [[DefrostingIceQueen every]] [[JustFriends trope]] mentioned on this page.
377* In ''Webcomic/TheGreenhouse'', Liv is very used to flirting and seducing, but actually falling for Mica is more than she knows what to do with.
378* [[TheGoomba Bogey]] of ''Webcomic/KidRadd''. Sure, he always hits on her (and everyone else) because she's hot, but late into the comic, he realizes he's actually fallen for [[spoiler:Sheena]], but only adds to his feelings of utter uselessness because he can plainly see that [[spoiler:she and Radd are meant to be]].
379* A rare gender-inversion with [[{{Tsundere}} Mora]] towards [[ThePhilosopher Minos]] in ''Webcomic/LasLindas''. [[spoiler: They do get together.]]
380* ''Webcomic/MagickChicks'': Faith has got it bad, for Tiffany.
381** She's the most sought-after girl at [[AllGirlSchool Artemis Academy]], to such an extent that [[ThePornomancer even her enemies lust after her.]] As such, she has no shortage of willing partners. Yet [[http://www.magickchicks.com/strips-mc/enjoying_the_perks it's Tiffany who has her heart.]] Faith has even said she'd stop seeing other girls, [[http://www.magickchicks.com/strips-mc/take_things_slow if Tiffany asked her to.]]
382** For a time, the readers doubted her sincerity (and some still do), because [[ReallyGetsAround she continues to sleep around.]] Nor is she bothered by the fact that her boyfriend, Ash, sees other people behind her back. Just as [[http://www.magickchicks.com/strips-mc/a_little_forward_-_ec_crossover_strip she was unfazed]] by the sight of Melissa kissing girl-Kade. Yet she became jealous, for the first time ever, when she saw [[spoiler: [[http://www.magickchicks.com/strips-mc/forces_of_darkness Amelia kiss Tiffany]]]].
383* Zii, the resident gleefully bisexual [[HandsomeLech Cute Lech]] (or [[DepravedBisexual amorally perverted sex criminal]], depending on who you ask) from ''Webcomic/MenageA3'', [[http://www.menagea3.net/strips-ma3/giggling_schoolgirl wound up heading down this road]]... [[http://www.menagea3.net/strips-ma3/like_any_other without brakes]]. [[spoiler: Unfortunately a combination of [[ButLiquorIsQuicker excess]] [[InVinoVeritas alcohol]], a seductive ex-lover, a willing (and hot) roomie, and horribly bad timing led to much crashing and burning (strip #749, May 31, 2013, NSFW). In fact, that strip may prove that Zii is equally in love with [=DiDi=], in a slightly different way -- depending on your definition of "love" and your view of [=DiDi's=] apparently supernatural sex appeal.]]
384** Matt, who's also bisexual, and goes through men and women like tissue paper, eventually falls for Kiley. [[spoiler:He goes through a rough patch when they break up.]]
385* The [[UnholyMatrimony relationship between]] [[SuccubiAndIncubi Sabine]] and [[EvilTwin Nale]] in ''Webcomic/TheOrderOfTheStick'' is strongly implied to be a gender-inverted example, although Sabine can't and doesn't try to deny her sex-demonic nature. Then again, as Nale is committed to Evil, he doesn't seem to care about what she does so much as ''how'' she does it (read: 4 flings in 3 hours, plus errands to run).
386* ''Webcomic/OutThere'':
387** Rod is genuinely in love with [[LipstickLesbian Ari]]. You'd think it'd be a straight IncompatibleOrientation, but it's… much more complicated. He's still sleeping around but has made it perfectly clear that [[ReformedRake he'd give it up in a heartbeat if she ever decides she wants him.]] [[http://outthere.keenspot.com/d/20090328.html]]
388** Wally's philandering ways began well [[http://outthere.keenspot.com/d/20060913.html before]] his marriage to Rebecca, and continued [[http://outthere.keenspot.com/d/20070427.html after they were wed]]; when he quit playing around, however, it seems he [[http://outthere.keenspot.com/d/20100126.html quit for good]].
389** Steven fell in love with Sherry, and later, Miriam, [[http://outthere.keenspot.com/d/20090605.html]], but was unable to maintain fidelity to either of them [[http://outthere.keenspot.com/d/20090220.html]] [[http://outthere.keenspot.com/d/20090815.html]].
390* Sven from ''Webcomic/QuestionableContent'' is an interesting example. He appears to give up his womanizing ways because of his friendship with [[{{Tsundere}} Faye]]. Then [[http://www.questionablecontent.net/view.php?comic=1079 then]] they start [[http://www.questionablecontent.net/view.php?comic=1198 sleeping together;]] it's not a serious, monogamous relationship, but Faye makes it clear that if she finds out he's been sleeping around, [[http://www.questionablecontent.net/view.php?comic=1307 she'll leave him in an instant.]] [[spoiler: [[http://www.questionablecontent.net/view.php?comic=1334 He then has a one-night-stand]], instantly regrets it, and [[http://www.questionablecontent.net/view.php?comic=1341 confesses to Faye]] -- and she leaves him in an instant. The incident makes [[http://www.questionablecontent.net/view.php?comic=1343 both]] [[http://www.questionablecontent.net/view.php?comic=1372 of them]] feel worse than they expected, and [[http://www.questionablecontent.net/view.php?comic=1650 hundreds of strips later, Sven is almost unrecognizable compared to his pre-Faye appearances.]]]]
391* ''Webcomic/{{Sinfest}}'':
392** Slick shows genuine love for Monique but is unable to express it properly. Of course, he isn't a real ladykiller, but since he fancies himself one and still pursues the status, it qualifies.
393** Also, Fuchsia is a seductress devil who is showing deep feelings for Criminy.
394* [[WholesomeCrossdresser Tip Wilkin]] of ''Webcomic/SkinHorse'' has this happen to him in a story arc in which he meets MadScientist Tigerlily Jones. He loses his superpower ability to make any woman fall into his bed, and even loses the ability to pick handcuffs with a bobby pin. Don't ask why he would need to.
395* Eric of ''Webcomic/VenusEnvy'' well and truly qualifies. In spite of the creepiness of TheCasanova being front and center, he's shown himself to be AboveTheInfluence. He's also [[UnsettlingGenderReveal not in possession of all the relevant facts]].
396* Joe Rosenthal of the Webcomic/{{Walkyverse}} comics, whose defining trait is his blatant sexism and sexual magnetism, falls into this after finding love on an Internet forum and eventually settling into his first monogamous relationship with his crush. Said crush goes missing, however, and to cope with the loss he regresses deep into his old habits.
397[[/folder]]
398
399[[folder:Web Original]]
400* ''WebVideo/CriticalRole'':
401** A female example, with Vex. She's a bit of a flirt and a MsFanservice, but she falls hard for [[spoiler: [[TheSmartGuy Percy]]]] after he [[spoiler: gives her a noble title]], and afterwards she acts like more of an awkward mess around him.
402** Scanlan, from the same series, declares his love for [[TheHeart Pike]] from day one, but eventually realizes that [[LovingAShadow he's only been idealizing her]]. He apologizes to her and decides to get to know her as a person before making any further advances. [[spoiler:They do get together in the epilogue, and when she tells him she'll "give [him] freedom", he tells her "The most free I've ever been is with you"]].
403* ''Literature/TheQuestportChronicles'': [[SerialRomeo The Lord of Angels and Demons]], to the [[ActionGirl Queen of Rogues and Robbers]].
404[[/folder]]
405
406[[folder:Western Animation]]
407* ''WesternAnimation/{{Archer}}'':
408** Archer with Katya Kasanova in "Double Trouble" [[spoiler:and "Skin Game".]] Cyril initially assumes that it's just another passing fancy; only [[OOCIsSeriousBusiness after finding out that Archer quit drinking for her does he realize that he really does care about her]].
409** Implied throughout the series [[spoiler:and confirmed in "Sea Tunt"]] that Archer really does love Lana, but he doesn't know how to say it.
410* ''Franchise/AvatarTheLastAirbender'':
411** This is revealed to be part of Avatar Kuruk's BackStory. Unfortunately, the spirits (well, one particularly creepy one) decided he changed his ways just a little too late. Tragedy ensues.
412** Bolin in ''WesternAnimation/TheLegendOfKorra'' has an eye for the ladies while being a genuine NiceGuy and pretty much falls in love with the main character [[LoveAtFirstSight at first sight]]. Unfortunately, Korra only has an interest in his brooding brother Mako and drama ensues when Korra goes on a NotADate with Bolin then kisses Mako (unknowingly) in front of him. After the triangle is resolved, Bolin continues looking for love in Season 2 (with some literally painful results with Korra's cousin and his costar in "movers") before [[spoiler: meeting Opal in Season 3 and finally getting a good girl of his own]].
413* ''WesternAnimation/FamilyGuy'' pairs this with WeWantOurJerkBack in the episode where Quagmire falls in love with the Griffins' temporary housekeeper, Joan.
414** "Jerome is the New Black" reveals that Quagmire became a heartless sex hound because the one woman he truly loved (Cheryl Tiegs) dumped him, which plays this trope for drama and provides a FreudianExcuse as to why Quagmire is the way he is. A later episode, "Tiegs for Two" got more in-depth with this.
415* ''WesternAnimation/{{Jem}}'':
416** Riot is a flirtatious musician who attracts women like bees to honey. There is only one woman he is genuinely interested in: Jem, who he sees as his perfect match. Unfortunately for him, Jem doesn't like him back. Or at least she doesn't in ''most'' episodes (a few, like "Riot's Hope" and "The Day The Music Died", imply otherwise).
417** Gender-swapped with Riot's bandmate Minx. As her nickname suggests, she's known for her seductive ways. She's attracted to Rio precisely because he's the one guy who [[AbhorrentAdmirer turns down her advances]]. A late episode also [[ShipTease implies]] she and Techrat, [[HatesBeingTouched of all guys]], could have a thing together someday.
418* Boomhauer from ''WesternAnimation/KingOfTheHill''. He manages to get women crawling all over him, even if they have only just seen him, and actively avoids getting into a serious relationship. But when he does actually fall in love, he gets a cruel and ironic backlash when the woman in question turns out to be using him even more cruelly than he ever used any other woman: she can't get his name right, can't understand half of what he's saying, and tells him, while he's kneeling on her doorstep after ''proposing'' to her, that "Actually, whenever you talk, I'm usually just nodding and smiling while waiting for your pants to come off." Can you say "Ouch"?
419* As revealed in the prequel novel ''Literature/ANewDawn'', rogue Jedi Kanan Jarrus of ''WesternAnimation/StarWarsRebels'' was a serious womanizer before falling completely head-over-heels in love with Hera Syndulla. After years of a loving partnership, [[spoiler:he gives his own life to save her, their crew...and their unborn son]].
420* Alejandro from ''WesternAnimation/TotalDrama''. He flirted with almost all the female contestants during the third season but ended up falling for [[spoiler:Heather]].
421* Brock Samson from ''WesternAnimation/TheVentureBrothers'' has a freakish ability to bed anyone who comes near him, but "the only woman he ever loved" was Molotov Cocktease, a badass Russian assassin who wears a chastity belt. He freely has sex with other women in spite of Molotov though, since even though he loves her, they can't enter into a relationship together. They have a history of personal vendettas which always leads to them both trying to kill one another. The fact she never puts out also might have something to do with it.
422[[/folder]]
423
424[[folder:Real Life]]
425* Creator/WarrenBeatty, A.K.A. "Warren Beauty," and his wife Creator/AnnetteBening, who managed to do what women like Julie Christie, Diane Keaton, Carly Simon, and ''{{Music/Madonna}}'' could not. They've been married for going on thirty years and have four kids: Stephen, Benjamin, Isabel, and Ella.
426* Gene Simmons from Music/{{KISS}} had a reputation for having sex with thousands of women but is deeply in love with his current companion Shannon Tweed. They even have a pretty stable family with a couple of kids, and finally tied the knot on October 1st, 2011.
427* [[http://en.wikipedia.org/wiki/Julio_Iglesias Julio Iglesias]] was known as a jet-set man ever since his divorce from Filipina Isabel Preysler. However, he met the model Miranda Rijnsburger in TheEighties, and they've remained together. They eventually got married in 2010.
428* This is how the media treated perpetual bachelor Creator/GeorgeClooney when he eventually got engaged and tied the knot in 2014.
429* Wrestling/CMPunk is notorious for the numerous relationships he's had in wrestling ''alone''. The actual list would probably boggle the mind, so a lot of fans were genuinely surprised when he got engaged to sweet, geeky Wrestling/AJLee. They were even more stunned when, even after walking out on the WWE, the engagement lasted and he ''married'' her, by all accounts indicating this trope.
430* UsefulNotes/JulieDAubigny was almost as famous for leaving a trail of broken hearts, male and female alike, all over France, as she was for her opera career and brushes with the law. However, in the last few years of her career, she was the mistress to Marquise de Florensac, and by all accounts, Julie was truly in love with her. So much so, that after the woman died, Julie was completely inconsolable, retiring from the opera and from public life. Where, exactly, she went is unclear, but most people agree she probably went to a convent, where she likely [[DeathByDespair died of a broken heart]].
431* The dashing and extremely handsome Luftwaffe AcePilot Hans-Joachim Marseille was a notorious womanizer with a long and impressive list of conquests which allegedly included a German general's wife, a Hungarian countess, singer Nilla Pizzi, and actress Zarah Leander. While stationed in France, he stole his commanding officer's car several times to drive into town and pick up girls. His womanizing was so extensive that it affected his career, and his superior officer finally had enough and transferred him to North Africa to keep him away from the French ladies. Taking all of this into account, everybody was surprised when Marseille announced his engagement to a Berlin teacher by the name of Hanne-Lies Küpper. Sadly, he would never get to marry her as he died the same year, at the young age of twenty-two.
432[[/folder]]

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