->'''Lily''': Barney, how can you be in love and still be sleeping with anything that moves?\\
'''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?
-->-- ''Series/HowIMetYourMother''

TheCasanova 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]].

Basically, [[LovableSexManiac the]] man(whore) ''genuinely'' [[CharacterDevelopment falls in love]].

It 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.

A common effect is that the charming ways that made them such winners with the ladies fall apart under the pressure of really wanting to charm her: fluent flirtation turns to GibberishOfLove and/or CanNotSpitItOut.

Most of the time, the character gives 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 interest.

Compare LookingForLoveInAllTheWrongPlaces. CantActPervertedTowardALoveInterest can result from this, and if combined with MadonnaWhoreComplex, the Casanova themselves may be the one who SleepsWithEveryoneButYou.


[[folder:Anime and Manga]]
* 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.]]
* Go Katou from ''Manga/AiShiteNight'' has quite the ladykiller fame, but when he develops feelings for GirlNextDoor Yakko, he falls ''hard'' for her.
* Kail Mursili from ''Manga/AnatoliaStory'', 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.
* Raphael from ''Manga/AngelSanctuary.'' Of course, [[LoveHurts it ends badly]].
* Apparently, both [[spoiler:Antonio Fabiani AND Leonardo Cardinale]] of ''Anime/AshitaNoNadja'', in regards to the same girl: [[spoiler:Julietta Satori]].
* Canon-wise, Greece from ''Webcomic/AxisPowersHetalia'' 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).
* 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.
* Ian is this in ''Manga/ACruelGodReigns'', although it stinks for him the Jeremy is his ForbiddenFruit.
* In the ''Franchise/EvilliousChronicles'' there's a villainous example with Sateriasis Venomania of ''LightNovel/TheLunacyOfDukeVenomania'', who is a Casanova of the type that [[Webcomic/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.
* ''LightNovel/TheFamiliarOfZero''
** 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.
** 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.
* Indications are that this is the case for ''Lightnovel/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.]]
* 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.
%%* Mariko Nakasu from ''Manga/GokinjoMonogatari''.
* 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 gangraped and he shot him dead in self-defense]], until Shuichi helps him overcome it.
* In some ''Manga/HanaYoriDango'' continuities, the F4's resident Casanova Soujiro falls for Tsukushi's best friend Yuki.
* In ''Manga/HappyYarouWedding'', former "King of the Night" Akira Todou falls in love with his housekeeper/nanny.
%%* Chizuru for Azumi in ''Hen''.
* ''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.
* ''Literature/TheHeroicLegendOfArslan'' has Gieve, smooth-talking [[TheCasanova Casanova]], falling head over heels for LadyOfWar Farangis who ignores his advances.
* 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.
* [[ChivalrousPervert Miroku]] from ''Manga/InuYasha'' falls hard for [[ActionGirl Sango]]. He still hits on anything in a skirt, though. [[spoiler:They marry anyway.]]
* Both Tomoe and Kurama from ''Manga/KamisamaKiss'' and both end up falling for the heroine, Nanami.
* 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.
* Kanba Takakura from ''Anime/MawaruPenguindrum''... towards [[BrotherSisterIncest his sister]] Himari.
* ''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.
-->'''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?
-->'''Mikoshiba:''' Well, yeah...
-->'''Kashima:''' ''Then why doesn't Senpai like me?! I don't get it!''
* 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.
* In ''Manga/OnePiece'', ChivalrousPervert Sanji falls rather hard for the local pigtailed girl 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.]]
* Tamaki of ''Manga/OuranHighSchoolHostClub'' towards Haruhi.
* George Koizumi in ''Manga/ParadiseKiss'', with a twist: [[spoiler:it's towards ''Kaori'' and not Yukari.]]
* Kairi from ''Manga/PeachGirl'', toward the female lead Momo.
* 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.
* ''Anime/SuperDimensionCavalrySouthernCross'', has former 15th squad commander and notorious player, Charles de Etouard, falling madly in love with AcePilot Mary Angel.
* ''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.
* ''Maybe'', [[HandsomeLech Shuutarou Mendou]] from ''Manga/UruseiYatsura'' - after he meets his rival's beautiful little sister, [[ShrinkingViolet Asuka]] [[ExtraordinarilyEmpoweredGirl Mizunokuji]].
* In ''Manga/VirginLove'', Daigo becomes this after meeting [[IfItsYouItsOkay Kaoru]]. Kaoru also qualifies as a mankiller (maneater?) in love when he finally comes around.
* 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.
* 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.

[[folder:Comic Books]]
* 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 makeout session nearly kills Gambit.
* 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.

[[folder: Fan Works]]
* 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.
* 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.
* ''Fanfic/PonyPOVSeries'': Thunderchild is an outrageous flirt, but acts unusually shy and chivalrous around Fluttershy.
* ''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]].
* ''[[https://www.fanfiction.net/s/12290311/1/The-Black-Emperor The Black Emperor]]'' has an unusual mutual example of this. [[ChivalrousPervert Lelouch]] and [[AnythingThatMoves Milly]] are truly, deeply in love with each other, but that doesn't stop either of them from sleeping with other girls.
* The [[RanmaOneHalf Ranma]]/FutabaKunChange story ''[[https://www.fanfiction.net/s/312018/1/Golden-Linings Golden Linings]]'' has infamous philanderer Futana finding herself falling for Ranma, with the latter loathing the former due to [[GenderBender Futana's]] lecherous advances on [[GenderBender her]], and Futana doesn't know what to do to overcome her history. It comes to a head when Ranma's father gets attacked and needs a rare bloodtype 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 have to struggle with Ranma's upbringing and Futana's past.

[[folder:Film -- Animated]]
* Prince Naveen from ''Disney/ThePrincessAndTheFrog''. He 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:
-->'''Naveen''': I am having troubles.\\
'''Ray''': Ya got that right, bro. You in love.\\
'''Naveen''': I know. It is horrible!\\
'''Ray''': But it's the good kind of horrible.\\
'''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...\\
'''Ray''': Yeah, that's love, all right.
* Despite Tramp's escapades with Lulu and Fifi and Trixie--not to mention Rosita Chiquita Juanita Chihuahua--he eventually falls for Lady in ''Disney/LadyAndTheTramp''.

[[folder:{{Film}} -- Live Action]]
* 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.
-->'''Face''': You knew I was a player, and you wanted to play. Then I wanted to get serious and you couldn't handle it.
* The 70's 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.
* This is the plot for the Heath Ledger version of ''Film/{{Casanova}}''.
%%* ''Film/CrazyStupidLove'': Jacob for Hannah.
* Also done in ''Film/CruelIntentions'', the modern-day adaptation of ''Literature/DangerousLiaisons''. Neither end well.
* 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.]]
* In ''Film/DonJuanDeMarco'', this is the title character's problem throughout the film.
* 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.
* 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.
* Wes from ''Film/TheDuff'' was a notorious womanizer [[spoiler:until he predictably falls for his childhood friend Bianca towards the end of the film]].
* 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.
* Averted in ''Film/{{Hitch}}'', where the eponymous character ''can'' be a 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.
* Tony Stark from ''Film/IronMan'' is a filthy rich, brilliant, narcissistic Casanova who is clearly in love with his long-time (and much beleaguered) assistant Pepper Potts.
* Peter Quill/Star-Lord from the ''Film/GuardiansOfTheGalaxy'' films. He 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.
* This happens to Film/JamesBond twice, in ''Film/OnHerMajestysSecretService'' and ''Film/CasinoRoyale2006''. [[DownerEnding It ends badly]] in both cases, and the other Bond films imply that he became a ladykiller (or only sought out shallow meaningless flings all the more) because he had his heart broken.
** It's downplayed with Creator/PierceBrosnan's 007 because he wasn't given a romance which 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.
* In ''Film/LoveAffair'', notorious playboy Michel Marnet, whose love life and women are [[WorstNewsJudgmentEver internationally famous]], falls hard for nightclub singer Terry [=McKay=].
* This is the driving force behind ''Film/LoveAndOtherDrugs''.
* ''Loveless in Los Angeles'' has a guy get fed up with pining over a JustFriends women in college after she gets engaged to someone else when he was about to do his LoveConfession. This gives him a FreudianExcuse to become a LadyKiller, but then his old flame re-enters the picture, freshly divorced.
%%* ''Film/{{Ninotchka}}''.
* ''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.
* Done in Creator/MartinLawrence's film, ''A Thin Line Between Love and Hate''.
* The Vince Vaughn character (and to a degree the Owen Wilson character) in ''Film/WeddingCrashers''.
* Justin Long's character on ''Film/{{Hes Just Not That Into You}}''.
* 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.]]

* 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.
* Joe Morelli in the ''Literature/StephaniePlum'' series of novels.
* 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.
* Sebastian in ''Literature/TheGardellaVampireChronicles''.
* 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".
--> '''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.
** Same with her best friend Andrea and her love interest Raphael.
* 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]].
** 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:
--> "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?'"
* Henry Crawford of ''Literature/MansfieldPark'' claims to be this. 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.
* ''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.
* Happens a lot in many literary incarnations of the Don Juan legend, the OlderThanSteam UrExample.
* 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]].
* 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 have fallen in love with her.
* 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.
* ''Literature/AnneOfGreenGables'' series:
** 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, he falls head over heels for her. From then on, to the other girls' massive frustration, he has eyes for no one else.
** Kenneth Ford, the LoveInterest of Anne and Gilbert's youngest child, Rilla, is this, too, though it's not as clear.
* 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.
* Dex is eventually this for Emma in ''Literature/OneDay'' though it takes him a fair few years and many failed relationships to realise it.
* 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.
* 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.
%% * ''Literature/TheMortalInstruments'': Jace Wayland with Clary Fray, naturally.
* 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.
* ''Literature/TheStormlightArchive'': All throughout [[Literature/TheWayOfKings 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.
* 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.
* Adrian Ivashkov from ''Literature/VampireAcademy'' is a serial womanizer who fell hard for Rose Hathaway.
* 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.
* Romeo in the #Hashtag book series, never hides that 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.
* ''Literature/TheHungerGames'': Finnick Odair with Annie.
* 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.
* ''[[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.]]

[[folder:Live Action TV]]
* [[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 [[HeroesWantRedheads 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 initally 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]].
* 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".
* 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]].
* Over the course of two seasons and roughly forty episodes, Rick Series/{{Castle}} 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.
* ''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).
* Simon from ''Series/CombatHospital'' who grew to have quite serious feelings for Rebecca in the first season after starting off as DrJerk TheCasanova with a GirlOfTheWeek or two.
* Patrick, when he starts seeing Sally in later seasons of ''Series/{{Coupling}}''.
* Declan of ''Series/{{Degrassi}}'', known for flirting with other girls, falls hard for Holly J, who initially rejects his advances.
* 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.
* ''Series/{{ER}}'''s Doug Ross was established from the first episode as a grade-A womanizer... who was desperately in love with [[HelloNurse Carol Hathaway]].
* ''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 like he himself does with many of his one-night stands.
** A few years later, Bulldog falls for Roz who also rejects him.
* 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.
* Santana from ''Series/{{Glee}}''. After a lot of sleeping around, including with Brittany, she realizes that Brittany is all she really wants.
** 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.
** 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!
* 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.
* 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, home-owner, 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.
* Brendan Brady prides himself on not getting to invested in his conquests, but that all changes when he falls hard in love with Ste Hay on ''Series/{{Hollyoaks}}''.
* 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 new found love (at least until they actually [[DeconfirmedBachelor get together)]].
* 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.
* Shane from ''Series/TheLWord''. Multiple times, as it never lasts.
* Don Draper from ''Series/MadMen'' in the Season 4 finale and all of Season 5.
* 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...[[CrowningMomentOfHeartwarming 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 Unfortunate Implication 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.
* In season four 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]].
* 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.)
* 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).
* 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 from Japan. His feelings for her had never changed.
* Nathan on ''Series/OneTreeHill'' started as a JerkJock who'd do AnythingThatMoves. 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.
* 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.
* 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.]]
%%* Brian Kinney in ''Series/QueerAsFolk''.
* 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).
** Played straight in TheMovie where Leon falls for a woman and ends the story married with a child, but still doing his radio show.
* 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
* 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 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 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.
* ''[[Series/TheSuiteLifeOfZackAndCody The Suite Life on Deck]]'' has a {{Kidanova}} example in Zack Martin, who early in season three fell head-over-heels for the new girl Maya, and vowed to reform his womanizing ways for her sake.
* A season one 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.
* 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'').
* 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.
* Daniel on ''Series/UglyBetty'', at least once a season.
** Also Armando Mendoza, his equivalent in the original ''Series/YoSoyBettyLaFea''.
* Damon Salvatore with Elena/used to be Katherine in ''Series/TheVampireDiaries''.
* ''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 YourCheatingHeart behaviour).
* Kojo in ''Series/ZekeAndLuther'' developed feelings for Zeke's cousin Mia in the episode "Sludge".
* 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.
* 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.]]
* ''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 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.

* ''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...little did I know that girl was an assassin too."
* A musical example would be "Conquest" by Patti Page (later covered by the White Stripes).
* 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 in the first date, but as time passes he comes to develop feelings for her.
* "Fooled Around And Fell In Love" by Elvin Bishop.
* ''Stealing My Heart'' by Music/TheRollingStones 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."
* A common interpretation of [[Music/{{Vocaloid}} Kagamine Len's]] ''Spice''
* Music/RoxyMusic's songs often fall into this trope.
* Brooks & Dunn's "Brand New Man"
* Gender-inverted with Music/TheGoGos' (being an all-female band) "Lust to Love".
* Gender-inverted with "Maneater" by Blue Eyed Blondes. It... [[ImAHumanitarian doesn't]] [[{{Yandere}} end]] [[AxCrazy well]].
* "Brains" by Kim Cesarion is about a promiscuous man who falls for a woman.
* The ''Music/StudioKillers'' song "Grand Finale" is about a woman in this situation after she falls in love with another woman:
-->I've been a dirty bastard but I will clean my act up.
-->I wanna stop doing bad.
-->I wanna meet your mom and dad.
* The Marshall Tucker Band's "Heard It In A Love Song".
* 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:
-->This woman's in love with you baby
-->This woman don't think you can do no wrong
-->But I think it's only fair to warn you
-->This woman don't stay in love for long

[[folder:New Media]]
* Liam of ''Website/GaiaOnline'' eventually develops real feelings for Sam, as opposed to meaningless flirting.

[[folder:Newspaper Comics]]
* 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.

* Harold Hill in ''Theatre/TheMusicMan'' finds himself too attached to Marian to make the timely getaway from River City he had originally planned.
-->"For the first time, I got my foot caught in the door."
* 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."
* Maureen from ''Theatre/{{Rent}}'' is a female, bisexual example. She'll sleep with ''anyone'', but has strong feelings for Joanne.
* 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.
* 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.
* 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.

[[folder:Video Games]]
* Sain in ''[[VideoGame/FireEmblemElibe Fire Emblem: Rekka no Ken]]'' 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 [[CryCute even breaks down crying]] for his "Princess".
** 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]].
** 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.
* In ''[[VideoGame/FireEmblemJugdral Fire Emblem: Seisen no Keifu]]'', 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]].
* 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.
** 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:
--->“I used to say this to all the ladies, but you're truly the only one for me.”
** Also implied in regards to Gaius. [[spoiler: Who ''also'' can be the dad of Inigo]]
--->"You're not the first to fall for me, but you're the only one I've cared about back."
* ''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.
* ''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.
* Junpei Iori from ''VideoGame/Persona3'' spends half the game drooling over girls, and, during the game's BeachEpisode, makes comments on the female party members' swimsuits that sends ShrinkingViolet Fuuka running to hide herself behind someone. Once he truly falls in love with [[spoiler: the DarkMagicalGirl Chidori]], though, he turns out to be a ChivalrousPervert who (depending on how the story's allowed to unfold) eventually [[IWantMyBelovedToBeHappy just wants his beloved to be happy]].
** He's also totally devoted to her. In the PSP remake, he's the only male S link the new GenderFlip protagonist can't have a romantic relationship with. Despite the fact that she could finish the S-Link before he even knows of his love interest. Some shippers aren't happy.
** Ryoji Mochizuki also qualifies as one 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.
* Vico's romance arc in ''VideoGame/ADanceWithRogues''. Also possibly gender-flipped with the player character.
* 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.
** 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]]).
* Pretty much the whole deal behind [[ChivalrousPervert Yuushi]] [[TallDarkAndHandsome Oshitari's]] paths in ''Manga/ThePrinceOfTennis'' {{Dating Sim}}s. Specially in ''Gakuensai no Oujisama'', where the main girl Shizuka even gets to see him get bitchslapped by an old girlfriend.
* 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.]]
* 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]].
* ''VideoGame/HarvestMoonDS Cute'': If you choose to go for Skye, a playboy thief. His lines get [[{{Adorkable}} cheesier]] with each heart event.
* ''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).
** 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 ]] ]]
* 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 [[AmazonChaser fur bikini]]... or a [[BareYourMidriff 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...
* In ''VideoGame/StarWarsTheOldRepublic'', this is a possible outcome of Doc's romance arc with a female Jedi Knight.
** 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.)

[[folder:Web Animation]]
* A oneshot 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.

[[folder:Web Comics]]
* 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.
* Sven from ''Webcomic/QuestionableContent'' is an interesting example. He appears to give up his womanzing 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.]]]]
* [[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]].
* 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 posession of all the relevant facts]].
* ''Webcomic/{{Sinfest}}'':
** 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.
** Also, Fuchsia is a seductress devil who is showing deep feelings for Criminy.
* Fox from ''Webcomic/BoyMeetsBoy'' and ''Webcomic/FriendlyHostility'' flirts with AnythingThatMoves, 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]].
* [[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.
* ''Webcomic/OutThere'':
** 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]]
** 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]].
** 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]].
* A rare gender-inversion with [[{{Tsundere}} Mora]] towards [[ThePhilosopher Minos]] in ''Webcomic/LasLindas''. [[spoiler: They do get together.]]
* ''Webcomic/GirlGenius'':
** [[http://www.girlgeniusonline.com/comic.php?date=20050817 Lars.]]
** Gil, given his parisian reputation (even if it's unclear whether it was a cover or not).
* Zii, the resident [[AnythingThatMoves 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.]]
** Matt, who's also BiTheWay, and goes through men and women like tissue paper, eventually falls for Kiley.
* 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.
* ''WebComic/MagickChicks'': Faith has got it bad, for Tiffany.
** 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.]]
** 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]]]].
* The [[UnholyMatrimony relationship between]] [[HornyDevils 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).

[[folder:Web Original]]
* ''Literature/TheQuestportChronicles'': [[SerialRomeo The Lord of Angels and Demons]], to the [[ActionGirl Queen of Rogues and Robbers]].
* ''WebVideo/CriticalRole'':
** A female example, with Vex. She's a bit of a flirt and a MsFanservice to boot, but she falls hard for [[spoiler: [[TheSmartGuy Percy]]]] after he [[spoiler: gives her a noble title]], and afterwards she acts like more of an {{Adorkable}} mess around him.
** Scanlan, from the same series, who declares his love for [[TheHeart Pike]] from day one, but eventually realizes that 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.

[[folder:Western Animation]]
* ''WesternAnimation/{{Archer}}'':
** 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]].
** 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.
* This is revealed to be part of Avatar Kuruk's BackStory on ''WesternAnimation/AvatarTheLastAirbender''. Unfortunately, the spirits (well, at least one particularly creepy one) decided he changed his ways just a little too late. Tragedy ensues.
* ''WesternAnimation/FamilyGuy'' pairs this with WeWantOurJerkBack in the episode where Quagmire falls in love with the Griffins' temporary housekeeper, Joan.
** "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.
* 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"?
* Alejandro from ''WesternAnimation/TotalDramaWorldTour''. He flirted with almost all the female contestants during the third season but ended up falling for Heather.
* 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.


[[folder: Real Life]]
* Creator/WarrenBeatty, aka "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.
* Gene Simmons from Music/{{KISS}} had a reputation of 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.
* [[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.
* This is how the media treated perpetual bachelor Creator/GeorgeClooney when he eventually got engaged and tied the knot in 2014.
* 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.