History Main / CasanovaWannabe

* ''ComicBook/TheFlash'': Though not his defining trait, ComicBook/WallyWest was known to be a skirt-chaser when he [[LegacyCharacter first took over the role after his uncle's passing]] in ''ComicBook/TheFlash1987''. In general, Wally was a manchild and this was part of it; he hit on every woman he could and while an attractive guy who was quite fun to hang out with (and thanks to being a MagneticHero, he often succeeded in being AmicableExes after the break-up), his immaturity was a constant turn-off. A ''big'' contributing factor to his CharacterDevelopment was him meeting [[OppositesAttract Linda Park]], who after initially disliking one another became FireForgedFriends and he developed a SingleTargetSexuality pretty much as soon as they started dating.

* From ''Franchise/{{Superman}}'': WGBS and Daily Planet sports reporter Steve Lombard, especially in ''ComicBook/AllStarSuperman''.

* ''Franchise/TheFlash'': Though not his defining trait, ComicBook/WallyWest was known to be a skirt-chaser when he [[LegacyCharacter first took over the role after his uncle's passing]]. In general, Wally was a manchild and this was part of it; he hit on every woman he could and while an attractive guy who was quite fun to hang out with (and thanks to being a MagneticHero, he often succeeded in being AmicableExes after the break-up), his immaturity was a constant turn-off. A ''big'' contributing factor to his CharacterDevelopment was him meeting [[OppositesAttract Linda Park]], who after initially disliking one another became FireForgedFriends and he developed a SingleTargetSexuality pretty much as soon as they started dating.

* Motor Ed in ''WesternAnimation/KimPossible'' incessantly puts the moves on Shego, ignoring hints (up to and including plasma blasts) that she's not interested.

* Rock from ''[[VideoGame/HarvestMoonAWonderfulLife Harvest Moon: Another Wonderful Life]]'' is this, to the point of even wearing a leisure suit and calling the main character "babe". He fails miserably at romance (though he fancies himself quite the catch) which is lampshaded by his mother, who questions your mental health should you pursue him.

->''"Is heaven missing an angel? 'Cause you got nice cans!"''
-->-- '''Dating Robot #1''', ''WesternAnimation/{{Futurama}}''

Sometimes the Casanova Wannabe ''talks'' a great game. He may have all his friends convinced that [[UrbanLegendLoveLife that he's the original ladies' man and that his bed is never cold]]. But the truth is, he still hasn't done it (or, if not, has only had bought-and-paid-for sex. Once. Which will be revealed in a pathetic and embarrassing tearful and/or drunken confession). Women can see the blinking neon "loser" sign bolted to his receding hairline a mile away. He clearly wants to prove his manhood via SexAsRiteOfPassage but hasn't managed it yet. If he has a job, it's likely as a LoungeLizard. In RealLife, the profane term "fuckboy" has become a current (likely soon to be outdated[[note]]Mainly because the term "fuckboy" is already in use in ''prison systems'' as slang term for inmates who are frequent targets for PrisonRape, thus making the term somewhat HarsherInHindsight[[/note]]) slang term for irritating young real-world Casanova Wannabe men, particularly those defined by a mix of boorish forwardness thinly disguised as flirtiness ("hehe and then what? ;)" and "wanna play the question game? ;)" being examples of their approach), mind games that are designed to allow him to put in the bare minimum of effort required to continue extracting sex from his target, and a massive sense of entitlement.

* Tatewaki Kuno of ''Manga/RanmaOneHalf'' straddles the line between this and HandsomeLech. He's wealthy and decent looking, and implied to have some slight luck in impressing the ladies, but his ego far outweighs his actual attractiveness. His "romantic" gestures tend to be either offensively forward ([[TheGlomp latching onto women without their permission]]) or insultingly narcissistic, and ''neither'' of the two girls he is smitten with even like him, much less find him attractive. Such is Kuno's ego that he ignores their violent retributions and blatant disgust, instead insisting that they are kept from him by the manipulations of his perceived arch-rival, Ranma Saotome. There are even some dark implications that Kuno is a potential rapist.

* ''WesternAnimation/JohnnyBravo'': The title character is a macho blonde musclehead who constantly tries (and fails) to get with the ladies, but his aggressive flirting almost always ends with him getting beaten up or otherwise humiliated. This actually turns out to be {{downplayed|trope}} as WordOfGod says Johnny does get lucky, it's just that his failures are make for funnier TV.

* Whenever Dr. Thaddeus S. "Rusty" Venture of ''WesternAnimation/TheVentureBrothers'' breaks out the hairpiece and polyester vest, you know you're in for a night of "Rusty's back!", despite the fact that he was never ''there''. He's not a virgin--he wouldn't have sons if he was - but he sure acts like it. Of his two known sexual encounters, neither was exactly healthy.
** Though he hasn't gotten laid in nineteen years.

* ''Fanfic/TheBoltChronicles'': Despite Blaze’s breadth of carnal experience, he is seemingly not very popular with the opposite sex.
** In "The Seven", Bolt’s mother has sex with him despite telling him he’s “not her type,” mistakenly thinking he's a stud male brought to the puppy mill for mating purposes. The three female dogs he first encounters there find him attractive initially, but express frustration when he can’t free them from their cages and tease him about his small size. As the story puts it in general:

** In "The Cameo", his girlfriend Tracey says she’s attracted to him, but doesn’t like him very much and speaks disparagingly of him. Not without reason.

* In Tim Dorsey's books about Serge Storms, a minor character is Johnny Vegas, who is handsome, wealthy, fun to be with... and cursed never to lose his virginity. He is always just about to when circumstances (often caused by Serge) intervene.

* In ''[[https://archiveofourown.org/works/14851212/chapters/42598331 Two Spiders on a Web]]'', an ordinary civilian hires ComicBook/SpiderGwen to babysit her children. Unfortunately, she lied about their ages; instead of being 7 and 5 like Gwen was lead to believe, they're 21 and 16. The older of the two tries flirting with Gwen by slapping her ass, but Gwen is having none of it and proceeds to web him up and leave.

%%* ''VideoGame/StarFox'''s [[RomanticFalseLead Panther]] [[LatinLover Caroso]]. '''Administrivia/ZeroContextExample'''

* ''VideoGame/BaldursGateIII'': Charismatic FolkHero warlock Wyll falls into this, as he's ballsy enough to try to flirt with [[BettyAndVeronica Lae'zel and Shadowheart]] ''at the same time'', and moves onto the PlayerCharacter after getting rebuffed. If chosen ''as'' the PlayerCharacter however, he's much more successful.