History Main / LadyKillerInLove

* Believe it or not, WesternAnimation/DonaldDuck used to be a rather successful Casanova before falling for Daisy and is still good at (unwittingly) attracting ladies in spite of being completely faithful to Daisy.
* ''ComicBook/TheFlash'': ComicBook/WallyWest, the third Flash, is probably one of the best examples of this in DC Comics. After graduating from his Kid Flash identity, Wally was characterised as being a player and constant flirt, with a large number of short-term love interests. Then in comes Linda Park; at first she's a reporter who he initially disliked, but developed into VitriolicBestBuds with, soaked in UnresolvedSexualTension. Eventually, they made it official, after which he became so devoted to her that their love was enough to overpower the pull of the Speed Force, making him both a more effective hero and showing he'd give up heaven for her. Notably, years later, Linda would seemingly be killed by the Black Flash, and later still erased from existence by Abra Kadabra, and in both scenarios, he's depicted as completely ignoring Jesse Quick (his DistaffCounterpart who had unrequited feelings for him and a healthy dose of ShipTease) because he'd loved Linda so much he'd developed SingleTargetSexuality, even when he didn't ''remember'' her.
* ''ComicBook/GreenArrow'' and ''ComicBook/BlackCanary'' are ''both'' an example (Canary being a gender-flipped version of this). Both Oliver and Dinah are typically depicted as being fairly active daters when they're not together, and flashbacks nowadays tend to present her as being the one to make the first move while Ollie is depicted as having once been a playboy. When they're written by a writer who likes both of them, their relationship tends to be presented as loving, mutually supportive, and very dedicated, but when they're ''not'' together they tend to have no issue playing the field.

* ''ComicBook/{{Nightwing}}'' is kind of a serial example of this; despite Dick Grayson having a reputation for being a ladies' man and being arguably the biggest MrFanservice in comics, when he falls for a woman he falls ''hard''. Barbara Gordon and Koriand'r are his two biggest loves, but he and ThirdOptionLoveInterest Shawn Tsang were also explicitly ''deeply'' in love.
* In college, ComicBook/ScottPilgrim used to be a successful casanova, with [[TheFriendNobodyLikes Julie]] warning her roommate against dating him by calling him a ladykiller to his face and providing examples. Said roommate was Envy Adams, the one who would make Scott fall for him... Making more tragic [[TheOneThatGotAway their eventual and devastating break-up]].
* ComicBook/{{Gambit}} and ComicBook/{{Rogue}} of ''ComicBook/XMen'' are a little different than the standard -- she accepts that he has genuine feelings for her, but since her powers mean they [[CantHaveSexEver can't touch each other ever]], she wishes he'd stop pursuing her and reminding her of what she can't have. There have been some hints of the two trying therapy to get around this problem, but, [[RuleOfDrama naturally]], it hasn't worked -- "Bizarre Love Triangle" is an excellent example, where despite Emma Frost's psychic therapy sessions, an attempted make-out session nearly kills Gambit. In the late 2010s though, they finally got around this, and now the two are a HappilyMarried BattleCouple.

* The ''Anime/RanmaOneHalf''/''Manga/FutabaKunChange'' story ''[[https://www.fanfiction.net/s/312018/1/Golden-Linings Golden Linings]]'' has infamous philanderer Futana finding herself falling for Ranma (currently in disguise as the girl "Yoiko Hibiki), being forced to takes things more chastely than usual for fear of Ranma's violent wrath towards perverted men. It comes to a head when Ranma's father gets attacked and needs a rare blood type that the Shimeru family happens to have. Futana realizes that this could be her way in, but [[IJustWantMyBelovedToBeHappy she can't bring herself to force anything onto Ranma]]. It does have an eventual happy if somewhat rough ending, when Ranma and Futana eventually get together, though they have to struggle with Ranma's insecurities about the idea of having sex with a guy, even if that guy is also Futana.

** Tony's father Howard is also established to have been a playboy drawn to one-night stands in ''Film/CaptainAmericaTheFirstAvenger'' and it's spin-off series ''Series/AgentCarter'', before appearantly settling down with Maria which whom he would latter have Tony.

* The protagonist of ''Webcomic/{{Alfie}}'' 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''.

* Lee Stetson/Scarecrow of ''Series/ScarecrowAndMrsKing'' gradually abandons his womanizing ways over the course of the series as he falls for (and eventually marries) Amanda King

* Invoked in ''Manhua/GoddessCreationSystem''. Xiaxi knows that Mingyi bores of anything he obtains easily, so she deliberately resists his advances. Not used to having women not fall to his charms, he pays more and more attention to her and becomes fixated on winning her over until he eventually falls in love.

%%* ''Film/CrazyStupidLove'': Jacob for Hannah.

* Daeran from ''VideoGame/PathfinderWrathOfTheRighteous'' is a spoiled, sarcastic hedonist who will sleep with AnythingThatMoves, if only once for the novelty, and his romance begins out as him seducing you partially for the fun of the chase (and because it will annoy his cousin, the queen of Mendev). Stick with him past the halfpoint of the game and especially during chapter 4 and he will begin to catch actual feelings for the Knight-Commander, [[spoiler:which is a huge problem for him because the EldritchAbomination that is [[DemonicPossession possessing him]] has a tendency of [[HeKnowsTooMuch tearing the heads off anyone who it suspects knows of its existence, which includes anyone gets close enough to Daeran to actually care for him as a person]]. Consequently Daeran will resist any attempt to get closer to him unless you're able to help him with his possession]]. Even before then, thanks to EvenEvilHasStandards, he considers it below him to cheat or double-time (he is accepting of {{Polyamory}}, but he is also the only LoveInterest to do so so it's a moot point anyway) and will remain faithful to the Knight-Commander if romanced.

* Deconstructed by [[VampiresAreSexGods Astarion's]] romance in ''VideoGame/BaldursGateIII''. He depicts himself early on as a frivolous player who will pretty much make a pass at every single person at camp, including the player, who he flirts with shamelessly on pretty much every occasion. If romanced, however, he'll actually reveal in his Act 2 LoveConfession that [[spoiler:he'd been falling back on his past instincts as a seductive lure for his [[IHateYouVampireDad abusive master Cazador]] and purposely seducing them in order to gain their loyalty and protection. He'll admit that his "plan" quickly fell apart when he fell in love with them for real.]]