Ladykiller in Love
Lily: Barney, how can you be in love and still be sleeping with anything that moves?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 them 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 Can Not Spit It Out. 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 his girlfriend. Compare Looking for Love in All the Wrong Places. Can't Act Perverted Toward a Love Interest can result from this.
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?
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?
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Anime and Manga
- Kairi from Peach Girl, toward the female lead Momo.
- Guiche in Zero no Tsukaima 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.
- Maybe, Shuutarou Mendou from Urusei Yatsura - after he meets his rival's beautiful little sister, Asuka Mizunokuji.
- Miroku from InuYasha falls hard for Sango. He still hits on anything in a skirt, though. They marry anyway.
- 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.
- George Koizumi in Paradise Kiss, with a twist: it's towards Kaori and not Yukari.
- Mariko Nakasu from Gokinjo Monogatari.
- Apparently, both Antonio Fabiani AND Leonardo Cardinale of Ashita no Nadja, in regards to the same girl: Julietta Satori.
- Canon-wise, Greece from Axis Powers Hetalia 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).
- Fanon-wise, France is often depicted as this in fanworks where he's paired with someone, especially if it's with Canada.
- In The Wallflower manga, womanizer Ranmaru is very clearly falling in love with his arranged fiancee Tamao (a commitment he originally tried to get out of), even if he hasn't fully realized it yet.
- 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.
- Raphael from Angel Sanctuary. Of course, it ends badly.
- 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.
- In some Hana Yori Dango continuities, the F4's resident Casanova Soujiro falls for Tsukushi's best friend Yuki.
- In ...Virgin Love, Daigo becomes this after meeting Kaoru. Kaoru also qualifies as a mankiller (maneater?) in love when he finally comes around.
- 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 gangraped and he shot him dead in self-defense, until Shuichi helps him overcome it.
- Chizuru for Azumi in Hen.
- In Happy Yarou Wedding, former "King of the Night" Akira Todou falls in love with his housekeeper/nanny.
- Kanba Takakura from Mawaru-Penguindrum... towards his sister Himari.
- The Heroic Legend of Arslan has Gieve, smooth-talking The Casanova, falling head over heels for Lady of War Farangis who ignores his advances.
- Touga from Revolutionary Girl Utena 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.
- Tamaki of Ouran High School Host Club towards Haruhi.
- 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.
- 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.
- Kuranosuke from Kuragehime towards Tsukimi, though he's in denial and she's rather clueless.
- Super Dimension Cavalry Southern Cross, has former 15th squad commander and notorious player, Charles de Etouard, falling madly in love with Amazonian Beauty and Ace Pilot Mary Angel.
- Tekkaman Blade II has David Kruegel, a known player who's in love with a woman he can never have in Aki Kisaragi, D-Boy's girlfriend.
- Ian is this in A Cruel God Reigns, although it stinks for him the Jeremy is his Forbidden Fruit.
- Both Tomoe and Kurama from Kamisama Kiss and both end up falling for the heroine, Nanami.
- Kail Mursili from Anatolia Story, for the time travelling lead girl Yuri. Everyone Can See It, too. And it's actually a plot point since Yuri happens to also be the one who fits the best to become Kail's Number Two, which makes her even more of a target from the Big Bad Nakia.
- 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.
- 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.
- In the Evillious Chronicles there's 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.
- Gekkan Shoujo 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!
- 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 makeout session nearly kills Gambit.
- Commander Hurricane in A Brief History of Equestria is historically famous for his sexual appetite 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.
Film — Animated
- Prince Naveen from The Princess and the Frog. He 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, alright.
- Despite Tramp's escapades with Lulu and Fifi and Trixie—not to mention Rosita Chiquita Juanita Chihuahua—he eventually falls for Lady in Lady and the Tramp.
Film — Live Action
- This is the driving force behind Love and Other Drugs.
- This is the plot for the Heath Ledger version of Casanova.
- 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.
- Also done in Cruel Intentions, the modern-day adaptation of Dangerous Liaisons. Neither end well.
- The Vince Vaughn character (and to a degree the Owen Wilson character) in Wedding Crashers.
- 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.
- The 70's 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.
- Tony Stark from Iron Man. A filthy rich, brilliant, narcissistic casanova who is clearly in love with his long-time (and much beleaguered) assistant Pepper Potts.
- 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.
- 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.
- In Don Juan De Marco, this is the title character's problem throughout the film.
- Crazy Stupid Love: Jacob for Hannah.
- 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.
- Loveless In Los Angeles has a guy get fed up with pining over a Just Friends women in college after she gets engaged to someone else when he was about to do his Love Confession. This gives him a Freudian Excuse to become a Lady Killer, but then his old flame re-enters the picture, freshly divorced.
- This happens to James Bond twice, in On Her Majesty's Secret Service and Casino Royale. It ends badly in both cases, and other Bond films imply that he became a ladykiller (or only sought after shallow meaningless flings all the more) because he had his heart broken.
- Done in Martin Lawrence's film, A Thin Line Between Love and Hate.
- 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.
- 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.
- In Love Affair, notorious playboy Michel Marnet, whose love life and women are internationally famous, falls hard for nightclub singer Terry McKay.
- Kalten in 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.
- Joe Morelli in the Stephanie Plum series of novels.
- 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.
- Sebastian in The Gardella Vampire Chronicles.
- 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.
- 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.
"'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 gamling! Bloody, bloody gambling and drinking! Where's my bloody drink? Anyone want to gamble for it?''"
- Don't let the marriage fool you though, he fully intends to keep drinking and gambling. His... insistance on reminding everyone of that fact is succinctly put by the ever stoically hilarious Talmanes:
- Henry Crawford of Mansfield Park claims to be this, but the heroine doesn't trust he can give up his ladykilling ways. She's right.
- Happens a lot in many literary incarnations of the Don Juan legend, the Older Than Steam Ur Example.
- 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.
- 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 have fallen in love with her.
- An entertaining example from a recent installment of The Vorkosigan Saga. Ivan 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 Anne of Green Gables series has 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 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.
- 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.
- 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.
- 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.
- All throughout The Way of Kings, first book of The Stormlight Archive, 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.
- Christian Grey in Fifty Shadesof Grey starts as a successful businessman who doesn't do romance, only interested in dominant/submissive relationships. However after proposing the protagonist Annastasia Steel a contract, he's willing to commit himself in a "vanilla relationship" with her.
- Adrian Ivashkov from Vampire Academy is a serial womanizer who fell hard for Rose Hathaway.
- 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.
Live Action TV
- 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).
- Brian Kinney in Queer as Folk.
- Damon Salvatore with Elena/used to be Katherine in The Vampire Diaries.
- 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).
- 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.
- 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 Your Cheating Heart behaviour).
- 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.
- 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 new found love (at least until they actually get together).
- 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.
- Shane from The L Word. Multiple times, as it never lasts.
- 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.
- Daniel on Ugly Betty, at least once a season.
- Also Armando Mendoza, his equivalent in the original Yo soy Betty, la fea.
- 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.)
- In season four 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.
- 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 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.
- 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 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.
- 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 Hollyoaks.
- Patrick, when he starts seeing Sally in later seasons of Coupling.
- 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.
- 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.
- A season one 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.
- 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 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.
- 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).
- 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.
- Nathan on One Tree Hill started as a Jerk Jock who'd do Anything That Moves. 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.
- 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.
- In the Japanese drama Nodame Cantabile, Dirty Old Man Stresemann had fallen in love with the school's principle 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 from Japan. His feelings for her had never changed.
- Kojo in Zeke and Luther developed feelings for Zeke's cousin Mia in the episode "Sludge".
- Declan of Degrassi, known for flirting with other girls, falls hard for Holly J, who initially rejects his advances.
- 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 Bad Ass 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!
- ER's Doug Ross. Established from the first episode as a grade-A womanizer. . .who was desperately in love with Carol Hathaway.
- Simon from Combat Hospital who 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.
- 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
- 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.
- 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.
- 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".
- Don Draper from Mad Men in the Season 4 finale and all of Season 5.
- 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, 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.
- 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.
- 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.
- 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.
- 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 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 Kagamine Len's Spice
- 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.
- Liam of Gaia Online eventually develops real feelings for Sam, as opposed to meaningless flirting.
- 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.
- 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."
- 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."
- Maureen from RENT is a female, bisexual example. She'll sleep with anyone, but has strong feelings for Joanne.
- 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.
- Sain in Fire Emblem: Rekka no Ken is a known flirt who usually shakes off women's rejection with a sad sigh and a continued effort to win them over. But in his supports with White Magician Girl Priscilla, when she gently tells him that a relationship between them wouldn't work out due to social status and location, he seems genuinely crushed by the revelation and even breaks down crying for his "Princess".
- In a variation, his supports with his best friend and long-time partner Kent show that he also may have feelings for their common lady of liege, Lyndis. However, he realizes that Kent also is in love with Lyn and his feelings might be deeper than Sain's own, so 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 trying to protect her 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 Fire Emblem: Seisen no Keifu, Alec is another Chivalrous Pervert who is pretty flirty towards the ladies in Sigurd's army. When he is paired up, though, he becomes quite loyal to his lover and partner.
- In Fire Emblem Awakening, Virion is a Chivalrous Pervert and fits in here if he's romanced by any of the girls.
“I used to say this to all the ladies, but you're truly the only one for me.”
- Played with in regards to Inigo who can be potentially fathered by Virion. He's a Handsome Lech and flirts around quite a bit in canon 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 if romanced by the female Avatar, though:
"You're not the first to fall for me, but you're the only one I've cared about back."
- Also implied in regards to Gaius. Who also can be the dad of Inigo
- 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.
- Junpei Iori from Persona 3 spends half the game drooling over girls, and, during the game's Beach Episode, makes comments on the female party members' swimsuits that sends Shrinking Violet Fuuka running to hide herself behind someone. Once he truly falls in love with the Dark Magical Girl Chidori, though, he turns out to be a Chivalrous Pervert who (depending on how the story's allowed to unfold) eventually 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 Gender Flip 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 A Dance with Rogues. Also possibly gender-flipped with the player character.
- 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.
- Isabela, the sexy pirate queen you can recruit for a threesome in Origins, has much deeper feelings for Hawke in Dragon Age II than she's initially willing to let on. Likewise, Anders—who flirts with more or less everybody in Awakening—gets dead serious for Hawke (though he also just gets dead serious in general).
- Pretty much the whole deal behind Yuushi Oshitari's paths in the Prince of Tennis Dating Sims. 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 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.
- 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.
- Harvest Moon DS Cute: If you choose to go for Skye, a playboy thief. His lines get cheesier with each heart event.
- 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).
- 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...
- In Star Wars: The Old Republic, this is a possible outcome of Doc's romance arc with a female Jedi Knight.
- Sven from Questionable Content is an interesting example. He appears to give up his womanzing 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.
- 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.
- 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 posession of all the relevant facts.
- 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 Boy Meets Boy and Friendly Hostility flirts with Anything That Moves, 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.
- 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.
- Out There:
- Rod is genuinely in love with Ari. You'd think it'd be a straight Incompatible Orientation, but it's… much more complicated. He's still sleeping around, but has made it perfectly clear that he'd give it up in a heartbeat if she ever decides she wants him. 
- Wally's philandering ways began well before his marriage to Rebecca, and continued after they were wed; when he quit playing around, however, it seems he quit for good.
- Steven fell in love with Sherry, and later, Miriam, , but was unable to maintain fidelity to either of them  .
- A rare gender-inversion with Mora towards Minos in Las Lindas. They do get together.
- Girl Genius:
- Gil, given his parisian reputation (even if it's unclear whether it was a cover or not).
- 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.
- 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.
- Magick Chicks: Faith has got it bad, for Tiffany.
- She's the most sought after girl at Artemis Academy, to such an extent that even her enemies lust after her. As such, she has no shortage of willing partners. Yet it's Tiffany who has her heart. Faith has even said she'd stop seeing other girls, if Tiffany asked her to.
- For a time, the readers doubted her sincerity (and some still do), because she continues to sleep around. Nor is she bothered by the fact that her boyfriend, Ash, sees other people behind her back. Just as she was unfazed by the sight of Melissa kissing girl-Kade. Yet she became jealous, for the first time ever, when she saw Amelia kiss Tiffany.
- 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.
- 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"?
- 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.
- This is revealed to be part of Avatar Kuruk's Back Story on Avatar: The Last Airbender. Unfortunately, the spirits (well, at least one particularly creepy one) decided he changed his ways just a little too late. Tragedy ensues.
- A oneshot 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.
- Brock Samson from The Venture Bros. 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.
- Alejandro from Total Drama World Tour. He flirted with almost all the female contestants during the third season but ended up falling for Heather.
- Real Life case: Warren Beatty, aka "Warren Beauty" and his wife Annette Bening, who managed to do what women like Julie Christie, Diane Keaton, Carly Simon and Madonna could not.
- Gene Simmons from 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.
- Julio Iglesias was known as a jet set man ever since his divorce from Filipina Hot Scoop Isabel Preysler. However, he met the model Miranda Rijnsburger in The Eighties, and they've remained together (though it's only recently that they got Happily Married.)
- This is how the media treated perpetual bachelor George Clooney when he eventually got engaged and tied the knot in 2014.