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Ladykiller in Love

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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?

The Casanova has scored dozens of women, never showing any real affection for any of them. However, maybe one of the girls, for whatever reason, is immune to his charms. Maybe he initially hates the girl, but then comes to appreciate her. Or maybe he's beginning to develop romantic feelings for a female friend of his.

Basically, the man(whore) genuinely falls in love.

It can be played for quite a lot of angst — how will the Handsome Lech convince his Love Interest that he's being genuine? Usually, this trope either humanizes or defangs the character. A staple for Romantic Comedy. Nine of ten male protagonists in Hispanic Telenovelas follow this trope and if the lead character of a Chick Flick is a man, you will see this in action.

A 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 Gibberish of Love and/or Cannot Spit It Out.

Most 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.

Compare Inconvenient Attraction, Reformed Rakes, Looking for Love in All the Wrong Places. Can't Act Perverted Toward a Love Interest can result from this, and if combined with Madonna-Whore Complex, the Casanova themselves may be the one who Sleeps with Everyone but You. See also More Experienced Chases the Innocent, which often involves a ladykiller pursuing a sexually and/or romantically inexperienced person and eventually falling in love with them.


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    Anime & Manga 
  • Roybea Roy of After War Gundam X 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 Subordinate Excuse for Captain Jamil and Roybea is quite aware of that. 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.
  • Sayoko Mishima of Ah! My Goddess is a gender-flipped version. She's beautiful, rich, and has all the men in the Nekomi Institute fawning over her, until 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, and before she realizes she ends up falling for him.
  • Go Katou from Ai Shite Night has quite the ladykiller fame, but when he develops feelings for Girl Next Door Yakko, he falls hard for her.
  • Raphael from Angel Sanctuary. Of course, it ends badly.
  • Apparently, both Antonio Fabiani AND Leonardo Cardinale of Ashita no Nadja, in regards to the same girl: Julietta Satori.
  • In some Boys over Flowers continuities, the F4's resident Casanova Soujiro falls for Tsukushi's best friend Yuki.
  • Ryo Saeba, the protagonist of City Hunter, is a notorious and successful Casanova in spite of his job as a Professional Killer, and is in love with his partner Kaori, even if he doesn't want to admit it.
  • Sho Naruse from Cheeky Brat has swarms of girls obsessing over him, but he himself is very committed to his relationship with Yuki.
  • Ian is this in A Cruel God Reigns, although it stinks for him that Jeremy is his Forbidden Fruit.
  • A villainous example with Sateriasis Venomania of The Lunacy Of Duke Venomania, who is a Casanova of the type that 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.
  • The Familiar of Zero:
    • 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 Really Gets Around — or at least used to, before falling for Saito and, after, Mr. Colbert.
  • Indications are that this is the case for Full Metal Panic!'s Lovable Sex Maniac Kurz Weber with regards to Melissa Mao, but they're not past the "slap" stage of Slap-Slap-Kiss in the anime. They finally end up together in the novels.
  • In Futari Ecchi, Matsuzaki's crush on 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.
  • Yuki from 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 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.
  • In Happy Yarou Wedding, former "King of the Night" Akira Todou falls in love with his housekeeper/nanny.
  • Hatsukoi Zombie'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 Ibusuki. He's utterly convinced he's a girl though (he's right), so it's a bit complicated.
  • The Heroic Legend of Arslan has Gieve, smooth-talking Casanova, falling head over heels for Lady of War Farangis who ignores his advances.
  • Canon-wise, Greece from Hetalia: Axis Powers might be this toward Japan, although his promiscuity isn't really his main character trait (apparently you can still be an all-around Nice Guy even if you have the honor of being at the top of sex frequency charts).
  • In Hot Gimmick, Hatsumi's younger sister Akane is known as the 'easiest' girl around in school, to the point where when she 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 Give Geeks a Chance, and the two end up as the series' Beta Couple.
  • In the Clear Moonlit Dusk: Ichimura makes it clear that despite his 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 Love at First Sight.
  • Miroku from Inuyasha falls hard for Sango. He still hits on anything in a skirt, though. They marry anyway, and he did at least stop asking other women to "bear his children" after they got engaged.
  • Both Tomoe and Kurama from Kamisama Kiss end up falling for the heroine, Nanami.
  • Wholesome Crossdresser Kuranosuke from Princess Jellyfish towards Tsukimi, though he's in denial at first. Tsukimi is rather clueless and ends up falling for his brother.
  • Monthly Girls' Nozaki-kun's Bifauxnen Kashima Yuu is a minor example. She's a proud Chick Magnet, 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!
  • Katarina in My Next Life as a Villainess: All Routes Lead to Doom! 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.
  • Never outright stated, but it's implied that Jiraiya of Naruto was in love with Tsunade, who always rejected him. One of his dying regrets was that he never managed to woo her.

    Comic Books 
  • Believe it or not, Donald Duck 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.
  • The Flash: Wally West, 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 Vitriolic Best Buds with, soaked in Unresolved Sexual Tension. 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 Distaff Counterpart who had unrequited feelings for him and a healthy dose of Ship Tease) because he'd loved Linda so much he'd developed Single-Target Sexuality, even when he didn't remember her.
  • Green Arrow and Black Canary 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.
    • 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.
  • 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 Mr. Fanservice in comics, when he falls for a woman he falls hard. Barbara Gordon and Koriand'r are his two biggest loves, but he and Third-Option Love Interest Shawn Tsang were also explicitly deeply in love.
  • In college, Scott Pilgrim used to be a successful casanova, with 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 their eventual and devastating break-up.
  • Gambit and Rogue of X-Men are a little different than the standard — she accepts that he has genuine feelings for her, but since her powers mean they 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, 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 Happily Married Battle Couple.

    Fan Works 
  • Commander Hurricane in A Brief History of Equestria is historically famous for his sexual appetite but fell in love with General Wind Whistler and later married Clover the Clever.
  • Piercing Gaze, the hero of A Long Night at the Hippodrome, is a Chivalrous Pervert who can't get his mind off The One That Got Away, the Great and Powerful Trixie Lulamoon. It's been almost a year since he's seen her, too.
  • Pony POV Series: Thunderchild is an outrageous flirt, but acts unusually shy and chivalrous around Fluttershy.
  • 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. 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.
  • The Black Emperor has an unusual mutual example of this. Lelouch and Milly are truly, deeply in love with each other, but that doesn't stop either of them from sleeping with other girls.
  • The Ranma ½/Futaba-kun Change! story 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 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.
  • The fic How Stormer Got Her Groove Back and especially its sequel involve the flirtatious rock-star Riot falling for Stormer.
  • In the One Piece fanfic 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.
  • In A Song of Ice and Fire fanfic The Cloak of Snow, Chivalrous Pervert 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 Just Friends 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.
  • Sirius Black from The Black Sheep Dog Series is a well-known 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.
  • 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 Velvet is straight. Normally this would not 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 Jaune Arc.
  • Returning Welsh Dragon: Issei, Harem Seeker extraordinaire, ends up falling for Ritsuka to such a degree that it borders on Single-Target Sexuality - 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.
  • The Story of Apollo, Daphne and Luca: An Italian Tragedy: Resident hearthrob Vincenzo falls genuinely in love for the first time ever with Luca.

    Films — Animated 
  • Asterix and the Vikings: Justforkix is apparently The Casanova 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 chief's daughter Abba, that he marries in the end.
  • Lady and the Tramp: Despite Tramp's escapades with several other dogs — Lulu, Fifi, and Trixie, and Rosita Chiquita Juanita Chihuahua — he eventually falls for Lady.
  • The Princess and the Frog: Prince Naveen makes the mistake of mentioning that he's dated thousands of women while attempting to 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.
  • Tangled: It doesn't come up in the movie itself, but the series implies that Flynn 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 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.

    Films — Live-Action 
  • Adam Sandler's character in 50 First Dates 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.
  • A plot point in The A-Team 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 '70s Australian sex comedy Alvin Purple. The title character is irresistible to women but falls in love with the one woman who's immune to his charms.
  • In Blonde Savage, 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 Jungle Princess Meelah.
  • The whole plot point of the movie Boomerang starring Eddie Murphy. He falls in love with the one woman he thinks is his equal. But soon finds out that she's an even more ruthless player than he is.
  • Crazy, Stupid, Love: 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.
  • Valmont from Dangerous Liaisons. However, it's arguably Deconstructed — he continues to sleep around and ultimately leaves the woman when asked to by his partner in Unholy Matrimony. He comes to regret it and instead of making things better, he decides to get himself killed.
  • Subverted in Don Jon. 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.
  • Don Juan: 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.
  • Ewan McGregor's character in the '60s rom-com pastiche Down with Love 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 feminist manifesto who seemingly wants nothing to do with him.
  • Wes from The Duff was a notorious womanizer until he predictably falls for his childhood friend Bianca towards the end of the film.
  • Averted in 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 Love Interest assumes he really does help guys get one-night stands and ends up ruining his career.
  • This happens to James Bond three times, in On Her Majesty's Secret Service, Casino Royale (2006). and Spectre/No Time to Die. It ends badly in all cases. For the first two, the subsequent Bond films imply that he became a 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 Second Love, only for HIM to die.
    • It's downplayed with Pierce Brosnan'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). Their deaths — the latter was even executed by his own hand — haunt him.
  • In Love Affair, notorious playboy Michel Marnet, whose love life and women are internationally famous, falls hard for nightclub singer Terry McKay.
  • Marvel Cinematic Universe:
    • In Iron Man, 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 (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.
    • Tony's father Howard is also established to have been a playboy drawn to one-night stands in Captain America: The First Avenger and it's spin-off series Agent Carter, before appearantly settling down with Maria which whom he would later have Tony.
    • In Guardians of the Galaxy (2014), 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.
  • Pirates of the Caribbean: Jack Sparrow has undoubtedly had a lot of companions over the years. Yet he admits to having only ever loved one: Angelica. This being Jack, it unsurprisingly doesn't stop him from ditching her.
  • The Sex Trip: 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.
  • Top Gun: Oh, Pete "Maverick" Mitchell. Ace Pilot, hotshot flyboy, and womanizer extraordinaire... who, in Top Gun: Maverick, is revealed to have been in a decades-long on-again, off-again relationship with admiral's daughter Penny Benjamin, with whom he is clearly head over heels in love. They go flying into the sunset together in his own personal P-51 Mustang at the end.
    Pete: I mean it. I'm never gonna leave you again.

  • Spider in Anansi Boys 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.
  • Anne of Green Gables 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 Love Interest of Anne and Gilbert's youngest child Rilla, is this too, though it's not as clear.
  • In Captain Vorpatril's Alliance, Ivan Vorpatril is sent by an acquaintance to pick up a girl, marries her to get cops who are being manipulated by the Disc-One Final Boss off her back, and then falls in love with her.
  • The Daevabad Trilogy has Muntadhir, who Really Gets Around and has apparently slept with most of his social circle, falling deeply in love with honourable, straight-laced Jamshid, 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 Arranged Marriage to somebody else.
  • Happens a lot in many literary incarnations of the Don Juan legend, the Older Than Steam Ur-Example.
  • In Fifty Shades of Grey, 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.
  • Fujimi Orchestra: 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.
  • In Gone with the Wind, 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 not Ashley but Rhett (who is also this trope towards her), but she realizes this a little too late.
  • Romeo in the 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.
  • In Howl's Moving Castle, Howl is a vain and 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.
  • Is It Wrong to Try to Pick Up Girls in a Dungeon?: Protagonist Bell Cranel initially sought to become an adventurer in order to win the hearts of cute girls... but when he gets 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 Oblivious to Love, but a bunch of other girls start actively chasing him then.
  • Kate Daniels' 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.
  • Handsome Lech Sergeant Jim Chopin in the Kate Shugak 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.
  • It's part of the initial setup for Last Song Before Night 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.
  • Magic's Price provides a Queer Romance 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. It's also Reincarnation Romance with a touch of soulmates mixed up into it.
  • Henry Crawford of Mansfield Park 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 From Bad to Worse.
  • Marcus of The Mark of the Lion has a reputation as The Casanova, but is intrigued by his sister’s slave girl who seems to be made of Incorruptible Pure Pureness despite liking him too, and eventually falls in love with her. The Relationship Upgrade is a long time in coming, however.
  • Mermaid Moon: After 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 Arranged Marriage.
  • In The Mister 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.
  • A Necklace of Fallen Stars: Alar of "The Player and the Knave" is the local heartthrob and he genuinely falls for Tantia.
  • In Of Fear and Faith, 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 Cannot Spit It Out.
  • Dex is eventually this for Emma in One Day though it takes him a fair few years and many failed relationships to realise it.
  • The first Red Dwarf 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.
  • 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 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. Too bad Mr Deal is a murderer.
  • Sense and Sensibility 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.
  • The Silerian Trilogy: Zimran, The Casanova, falls hard for Elelar, who is very similar to him in terms of her sexual habits (yet with 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.
  • The Stormlight Archive: All throughout 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, Words of Radiance, a preliminary betrothal is formed between him and fellow protagonist Shallan Davar, and they are fairly solidly in love before the book ends.
  • Pufftail from 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 Love at First Sight with her. However, Tammy died and Pufftail returned to his casanova ways to numb the pain.
  • In Tales of the Frog Princess, Prince Garrid, who's been described as a ladies' man, two-times Li'l and Princess 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.
  • Kalten in the The Tamuli series by David Eddings. 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 David Eddings series, as soon as said girl finds out, she clears that right up. Expressively.
  • In Toll the Hounds, book eight of the Malazan Book of the Fallen, 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 The Kharkanas Trilogy where he had the attention of every woman (and dragon) in sight but wasn't especially interested in any of those.
  • Adrian Ivashkov from Vampire Academy is a serial womanizer who fell hard for Rose Hathaway.
  • Mat from the Wheel of Time, he's such a Chivalrous Pervert that him falling in love with Tuon and marrying her was one of the signs of the apocalypse. 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 ever stoically 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?'"

    Live-Action TV 
  • 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.
  • At first, Danny from Baby Daddy seems like the typical hockey player who Really Gets Around, but backstory reveals that he's been in love with Riley since high school, even when she was still "Fat Pants".
  • Betty en NY:
    • 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.
    • Played With 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 Marcela, but the relationship went nowhere and he ended up bitter about it falling back into his old habits.
  • Happens twice with Shawn Hunter on Boy Meets World. 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. Even that one didn't pan out in the end.
  • 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.
  • Over the course of two seasons and roughly forty episodes, Rick 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 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 Establishing Character Moment was autographing a woman's chest, he's been married at least twice, and he commands a decent price in celebrity bachelor auctions.
  • Cheers. Sam Malone is the Trope Codifier, 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 Combat Hospital grew to have quite serious feelings for Rebecca in the first season after starting off as Dr. Jerk The Casanova with a Girl of the Week or two.
  • Patrick, when he starts seeing Sally in later seasons of Coupling.
  • Daredevil (2015):
    • 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).
    • 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 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.
  • Declan of Degrassi: The Next Generation, 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 Doctor Who, 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 Torchwood and was married at some point.
  • ER:
    • 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, nothing has changed.
    • 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 his roommate Neela Rasgotra. They also eventually become an Official Couple.
    • Simon Brenner's first episode establishes his womanizing ways, given that 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, she ultimately leaves him to reunite with Ray in Baton Rouge.
    • 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.
  • 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.
    • A few years later, Bulldog falls for Roz who also rejects him.
  • Joey on 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 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 Just Friends 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!
  • A Rare Female Example in Good Witch. 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.
  • Happened to Chuck on Gossip Girl, 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 Grey's Anatomy 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.
  • Hightown: Jackie starts out as a lesbian casanova in Season 1. During Season 2 though she gets into a committed relationship with Leslie, though it doesn't last.
  • 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 Hollyoaks.
  • Barney Stinson, quoted above from How I Met Your Mother. 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 get together).
  • In Kamen Rider Kiva, Otoya falls in love with Yuri. However, he ultimately falls in love with Maya, and Yuri ends up marrying another man off-screen.
  • The titular character of Lucifer 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?" as the Devil’s first love.
  • Shane from The L Word. Multiple times, as it never lasts.
  • Don Draper from Mad Men in the Season 4 finale and all of Season 5.
  • Though not part of the main storyline, this is the story of Hal and Lois in Malcolm in the Middle. 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 Unfortunate Implications 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.
  • Phryne Fisher of Miss Fisher's Murder Mysteries has quite happily shagged her way across several continents, but after an 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.
  • In Season 4 of NCIS, Tony DiNozzo finds himself in this position with Jeanne Benoit, with the added complication that he initiated the relationship as part of an undercover operation and was never supposed to actually fall in love with her.
  • Done in the Grand Finale of Night Court, where Dan vows to give up his Kavorka Man 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 Happily Married to another woman and is still in mourning several years after her death.
  • Similar to the above example, Ricky of Noah's Arc once he falls in love with Junito (he considers breaking his promiscuous ways, but it never pans out for long).
  • In the Japanese drama Nodame Cantabile, Dirty Old Man Stresemann had fallen in love with the school's principal when they were younger. But they decided to remain Just Friends 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.
  • Don Eppes of NUMB3RS becomes this when he falls in love with Robin. Though the "Ladykiller" part is more of an Informed Attribute than anything.
  • Nathan on One Tree Hill started as a Jerk Jock 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.
  • One episode of 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 Quantum Leap. It's established early on that Al is a Chivalrous Pervert 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 Bethnote  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. 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 Happily Married in 1999 and have had four daughters.
  • Titus Pullo from Rome is a Chivalrous Pervert 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. Sadly, it doesn't end well for the poor girl.
  • Parodied on Saturday Night Live (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 The Movie where Leon falls for a woman and ends the story married with a child, but still doing his radio show.
  • Lee Stetson/Scarecrow of Scarecrow and Mrs. King gradually abandons his womanizing ways over the course of the series as he falls for (and eventually marries) Amanda King.
  • Seinfeld's Kramer, generally confident in his ability to charm any woman, falls hard for Jerry's Girl of the Week 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.
  • Samantha on Sex and the City 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'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.
  • 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.
  • A Season 1 episode of Supernatural introduces us to Dean Winchester's New Old Flame 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 Dean actually got hurt.
  • Thanks: Burnaby is a world-traveling merchant who's been with countless women. When he meets Grammy, he wants to settle down with her.
  • Steven Hyde of That '70s Show when he falls in love with 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 break up several times due to Jackie's desire to get married one day. They finally find a resolution when 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.
  • Jack of Three's Company never fails to show up with a Girl of the Week, 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 Stalker with a Crush for him).
  • Owen Harper of Torchwood, the series' Kavorka Man, 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.
  • 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, the woman is much younger than him and very impulsive and he realizes she might come to regret their relationship. Even more unfortunately, she is engaged to his son. He attempts to Break Her Heart to Save Her, and, when that fails, plans to move to another city several thousand miles away. However, before he can do so, his son catches them together and murders him.
  • Turn plays this trope for drama and tragedy with Major John 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 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.
  • Daniel on Ugly Betty, at least once a season.
  • Damon Salvatore with Elena/used to be Katherine in The Vampire Diaries.
  • Velvet: Mateo works to give up his ladykiller ways once he genuinely falls for Clara. His difficulty adjusting to monogamy partially fuels the Slap-Slap-Kiss nature of their relationship.
  • Veronica Mars: Logan Echolls, who Really Gets Around, refers to most of his conquests as "playmates" or a variation thereof — but admits to genuinely loving Lilly Kane and Veronica Mars (and, with the latter, manages to not even slightly fall into adulterous behaviour).
  • Kojo in Zeke and Luther developed feelings for Zeke's cousin Mia in the episode "Sludge".
  • Logan Reese, from Zoey 101 seems to act like this after he starts dating Quinn, as he is not shown flirting with other girls after their First Kiss.

  • Invoked in Goddess Creation System. 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.

  • 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 on the first date, but as time passes he comes to develop feelings for her.
  • "Fooled Around And Fell In Love" by Elvin Bishop, used to a tee for the aforementioned Guardians of the Galaxy.
  • Stealing My Heart by The Rolling Stones 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 Ryuusei-P's 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.
  • Roxy Music's songs often fall into this trope.
  • Brooks & Dunn's "Brand New Man"
  • Gender-inverted with The Go-Go's' (being an all-female band) "Lust to Love".
  • Gender-inverted with "Maneater" by Blue Eyed Blondes. It... doesn't end well.
  • Brains Out by Kim Cesarion is about a promiscuous man who falls for a woman.
  • The Studio Killers 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 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
  • Confession Executive Committee ~Love Series~ ' "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").
  • Hunters and Collectors' "Ladykiller" is about a ladykiller who desperately wishes to be a ladykiller in love
  • 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.
  • Demi Lovato's "Heart Attack" is a Gender-Inverted Trope example.
    When I don't care I can play 'em like a Ken doll
    Won't wash my hair, then make 'em bounce like a basketball
    But you make me wanna act like a girl
    Paint my nails and wear high heels
    Yes, you make me so nervous that I just can't hold your hand

    New Media 
  • Liam of Gaia Online eventually develops real feelings for Sam, as opposed to meaningless flirting.

    Newspaper Comics 
  • Lois on Dykes to Watch Out For 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.

  • In Cactus Flower, 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.
  • Sky Masterson in Guys and Dolls 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."
  • In The Hunchback of Notre Dame, both Phoebus and Jehan are this towards, respectively, Esmeralda and Florika, as part of Jehan's Adaptational Heroism.
  • 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 ("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 Happily Married 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.
  • Harold Hill in The Music Man 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."
  • Maureen from RENT is a female, bisexual example. She'll sleep with anyone, but has strong feelings for Joanne.
  • Fiyero from 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.
  • Valentine in George Bernard Shaw'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.

    Video Games 
  • Vico's romance arc in A Dance with Rogues. Also possibly gender-flipped with the player character.
  • Deconstructed by Astarion's romance in Baldur's Gate III. 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 Love Confession that he'd been falling back on his past instincts as a seductive lure for his 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.
  • Part of the backstory of The Rogue, Lyndon, in Diablo III. 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 Fur Bikini... 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 turned to crime in order to fund his attempts to woo her and that she was so displeased that she ended up marrying his Nice Guy brother instead. The pain in his voice is audible whenever she comes up in conversation, turning his otherwise Loveable Rogue demeanor bitter in a split second...
  • A possible outcome in Dragon Age: Origins for the Depraved Bisexual 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 the Warden perish during the Final Battle, Zevran is unable to love anyone ever again in his life.
  • In Ensemble Stars!, 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 Audience Surrogate just because it'd be nice to have a girl to flirt with at school amongst 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.
  • Far Cry 3 has Dennis Rogers, a Liberian man welcomed into the Rakyat tribe who 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 Jungle Princess and leader of the Rakyat. Sadly, Citra is more interested in 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 at the cost of her life. Dennis has a My God, What Have I Done? 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."
  • Zidane Tribal, the protagonist of Final Fantasy IX, has this as a major part of his Character Development. He starts out as a fairly open skirt chaser (at the age of 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. Doesn't stop them from getting together in the end, though.
  • Fire Emblem:
  • Harvest Moon DS Cute: If you choose to go for Skye, a playboy thief. His lines get cheesier with each heart event.
  • Neverwinter Nights 2: 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.
  • Daeran from Pathfinder: Wrath of the Righteous 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 The Chosen One 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, which is a huge problem for him because the Eldritch Abomination that is possessing him has a tendency of 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 Even Evil Has Standards, he considers it below him to cheat or double-time (he is accepting of Polyamory, but he is also the only Love Interest to do so so it's a moot point anyway) and will remain faithful to the Knight-Commander if romanced. If the Knight-Commander sacrifices themselves to seal the Worldwound, the Where Are They Now epilogue for a romanced Daeran reveals he mourned them for the rest of his life.
  • Ryoji Mochizuki from Persona 3 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.
  • Pretty much the whole deal behind Yuushi Oshitari's paths in The Prince of Tennis Dating Sims. Especially in Gakuensai no Oujisama, where the main girl Shizuka even gets to see him get bitchslapped by an old girlfriend.
  • In Star Wars: The Old Republic, 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 Commitment Issues. If things progress well enough, he eventually overcomes these to remain with the female Sith Inquisitor.
  • Team Fortress 2: 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).

    Visual Novels 
  • Koujaku from DRAMAtical Murder is known to be The Charmer 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 they were children, and Koujaku stops picking up other women completely in his good ending.
  • Heo Ae-Jeong from Hate Plus 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. 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.
  • Tara Bryck from Heart of the Woods 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.
  • Ikemen Sengoku:
    • 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.
    • 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 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.
  • Derek in RE: Alistair, if you get his ending. He gets bonus points for initially flirting with Merui solely to play with and emotionally string her along, only to admit developing genuine feelings for her when she confronts him about this.
  • Starry Flowers: The 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.

    Web Animation 
  • A one-shot character in 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.

  • The protagonist of 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.
  • Gannet from 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.
  • Fox from Boy Meets Boy and Friendly Hostility 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 is genuinely heartbroken when Collin eventually breaks up with him.
  • The eponymous Roomie of Go Get a Roomie! doesn't mean to be a ladykiller — she maintains that she loves everybody equally and is dismayed whenever her Friends with Benefits inevitably fall for her. And then Roomie meets Lillian, who fits basically every trope mentioned on this page.
  • In The Greenhouse, Liv is very used to flirting and seducing, but actually falling for Mica is more than she knows what to do with.
  • Bogey of Kid Radd. 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 Sheena, but only adds to his feelings of utter uselessness because he can plainly see that she and Radd are meant to be.
  • A rare gender-inversion with Mora towards Minos in Las Lindas. They do get together.
  • Magick Chicks: Faith has got it bad, for Tiffany.
  • Zii, the resident gleefully bisexual Cute Lech (or amorally perverted sex criminal, depending on who you ask) from Ménage à 3, wound up heading down this road... without brakes. Unfortunately a combination of excess 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 bisexual, and goes through men and women like tissue paper, eventually falls for Kiley. He goes through a rough patch when they break up.
  • The relationship between Sabine and Nale in The Order of the Stick 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).
  • Out There:
  • Sven from Questionable Content is an interesting example. He appears to give up his womanizing ways because of his friendship with Faye. Then then they start sleeping together; it's not a serious, monogamous relationship, but Faye makes it clear that if she finds out he's been sleeping around, she'll leave him in an instant. He then has a one-night-stand, instantly regrets it, and confesses to Faye — and she leaves him in an instant. The incident makes both of them feel worse than they expected, and hundreds of strips later, Sven is almost unrecognizable compared to his pre-Faye appearances.
  • 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.
  • Tip Wilkin of Skin Horse has this happen to him in a story arc in which he meets Mad Scientist 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.
  • Eric of Venus Envy well and truly qualifies. In spite of the creepiness of The Casanova being front and center, he's shown himself to be Above the Influence. He's also not in possession of all the relevant facts.
  • Joe Rosenthal of the 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.

    Web Original 

    Western Animation 
  • Archer:
  • Avatar: The Last Airbender:
    • This is revealed to be part of Avatar Kuruk's Back Story. Unfortunately, the spirits (well, one particularly creepy one) decided he changed his ways just a little too late. Tragedy ensues.
    • Bolin in The Legend of Korra has an eye for the ladies while being a genuine Nice Guy and pretty much falls in love with the main character at first sight. Unfortunately, Korra only has an interest in his brooding brother Mako and drama ensues when Korra goes on a Not a Date 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 meeting Opal in Season 3 and finally getting a good girl of his own.
  • Family Guy pairs this with We Want Our Jerk Back! 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 Freudian Excuse as to why Quagmire is the way he is. A later episode, "Tiegs for Two" got more in-depth with this.
  • Jem:
    • 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).
    • 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 turns down her advances. A late episode also implies she and Techrat, of all guys, could have a thing together someday.
  • Boomhauer from King of the Hill. 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"?
  • As revealed in the prequel novel A New Dawn, rogue Jedi Kanan Jarrus of Star Wars Rebels was a serious womanizer before falling completely head-over-heels in love with Hera Syndulla. After years of a loving partnership, he gives his own life to save her, their crew...and their unborn son.
  • Alejandro from Total Drama. He flirted with almost all the female contestants during the third season but ended up falling for Heather.
  • Brock Samson from The Venture Brothers 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.

    Real Life 
  • Warren Beatty, A.K.A. "Warren Beauty," and his wife Annette Bening, who managed to do what women like Julie Christie, Diane Keaton, Carly Simon, and Madonna could not. They've been married for going on thirty years and have four kids: Stephen, Benjamin, Isabel, and Ella.
  • Gene Simmons from 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.
  • 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 The '80s, and they've remained together. They eventually got married in 2010.
  • This is how the media treated perpetual bachelor George Clooney when he eventually got engaged and tied the knot in 2014.
  • CM Punk 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 A.J. Lee. 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.
  • Julie d'Aubigny 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 died of a broken heart.
  • The dashing and extremely handsome Luftwaffe Ace Pilot 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.