Ladykiller in Love

"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?"

- How I Met Your Mother

The Casanova has scored dozens of women, never showing any real affection for any of them. However, maybe one of the girls is immune to his charms. Maybe he initially hates the girl, but then comes to appreciate her. Or maybe he just starts to see a female friend in a new way.

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 main character of a Chick Flick is male you will see this in action.

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, if 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.

Anime and Manga

 * Kairi from Peach Girl, toward the female lead Momo.
 * Guiche in The Familiar of Zero 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.
 * 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, and as of the novel Semaru Nick of Time,.
 * Fortunately we now know that he
 * George Koizumi in Paradise Kiss, with a twist:
 * Mariko Nakasu from Gokinjo Monogatari.
 * Apparently, both  of Ashita no Nadja, in regards to the same girl:.
 * 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 Tomoe (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 Aishite 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, 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, quite the smooth talking 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.

Comic Books

 * 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.

Film
"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."
 * Prince Naveen from The Princess and the Frog. He makes the mistake of mentioning that he's dated thousands of women while attempting to . A deleted scene has him discuss the trope with Ray:

"Face: You knew I was a player, and you wanted to play. Then I wanted to get serious and you couldn't handle it."
 * 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.
 * 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 the independent, modern-minded author of the eponymous feminist manifesto who seemingly wants nothing to do with him.
 * Keyword: seemingly. (Hey, it's Ewan McGregor, what healthy heterosexual woman (or human with a pulse) WOULDN'T want him?)
 * The 70's Australian sex comedy Alvin Purple. The title character is irresistible to women, but falls in love with the one 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.


 * 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 Demarco, 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 would later be burned) 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.

Literature
"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.""
 * 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".


 * 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.
 * Henry Crawford of Mansfield Park claims to be this, but the heroine doesn't trust he can give up his ladykilling ways.
 * Happens a lot in many literary incarnations of the Don Juan legend, the Older Than Steam Ur Example.
 * "Love-o'-Women" by Rudyard Kipling is about such a case.
 * 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.
 * 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 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.
 * Nealan of Queenscove from Tamora Pierce's Protector of the Small, has various crushes throughout the quartet on multiple noble ladies, up to and including the Queen. He has a tendency to make quite a lot of noise about these, writing (terrible) poetry and mourning to all and sundry the fact that all his crushes are hopelessly unrequited. However, when he falls in love with Yukimi noh Daiomoru, he is so tight-lipped about it that even his best friend Keladry of Mindelan has no clue how he feels about her until he faces his Ordeal.

Live-Action TV

 * Brian Kinney in Queer as Folk.
 * 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.
 * 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.
 * 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.
 * 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.
 * 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, 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.
 * 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 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!
 * 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 Beth 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.
 * 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.

Music

 * 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.

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.

Theatre

 * Harold Hill in The Music Man. "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.

Video Games

 * 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 variuation, 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 decides to support a relationship between them instead of pursuing Lyndis himself
 * 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.
 * 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, 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 for the Depraved Bisexual elf Zevran, if the PC (male or female) can get Zevran's approval meter high enough.
 * 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.
 * Derek in RE: Alistair, if you get his ending. He gets bonus points for.

Web Comics

 * Sven from Questionable Content is an interesting example. He appears to give up his womanzing ways because of his friendship with Faye. And then they started 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.
 * 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, but only adds to his feelings of utter uselessness because he can plainly see that.
 * 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 from Sinfest 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.
 * Tip Wilkin of Skin Horse has this happen to him in the current story arc when 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.
 * Rod from Out There 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.
 * In Girl Genius, Lars.
 * 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, is headed down this road... without brakes.
 * 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. However, it would appear that this trope no longer applies to him.
 * The relationship between Sabine and Nale in The Order of the Stick is strongly implied to be a gender-inverted example?
 * Implied? She outright admits that she sleeps around, and feels absolutely no guilt about it.

Web Original

 * The Questport Chronicles: The Lord of Angels and Demons, to the Queen of Rogues and Robbers.

Western Animation

 * 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.
 * This is revealed to be part of Avatar Kuruk's Backstory 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 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.
 * 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

 * Real Life case: Warren Beatty, aka "Warren Beauty", and his wife Annette Bening.
 * 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 1, 2011.
 * This
 * 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.)