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Casanova Wannabe

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"I know you think you're some kind of smooth-talking ladies man, but the truth is you're just pathetic and creepy."
Penny to Howard, The Big Bang Theory

He wants to be The Casanova, but he fails horribly. Maybe it's the polyester suit. Or the gold medallion around his neck. Or the phony "hey babe". Or the obvious hair plugs. Or the simple aura of sleaze. Or the mere fact that he's not as good-looking as he thinks he is. Whatever it is, though, the girls see it from a mile away and give him a wide berth.

Sometimes the Casanova Wannabe talks a great game. He may have all his friends convinced that 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 Sex as Rite-of-Passage but hasn't managed it yet. If he has a job, it's likely as a Lounge Lizard. In Real Life, the profane term "fuckboy" has become a current 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.

Generally he's bound to succeed once or twice, by law of averages if nothing else. These relationships usually don't last long. Sometimes he will "succeed" by attracting or scoring with an Abhorrent Admirer by accident (don't expect him to learn the right lessons from the experience, though).

Compare Nerds Are Virgins and Proud to Be a Geek. Contrast Kavorka Man (though, surprisingly, the two can overlap, as many Wannabes end up finding a fair bit of love anyway), Even the Guys Want Him. May overlap with The Schlub Pub Seduction Deduction, which occurs when a guy is so unattractive that if beautiful women are coming onto him, it's almost certainly for ulterior motives.

See Abhorrent Admirer for when an extremely unattractive character (in personality or appearance) is abhorred by the target of their affections. See Handsome Lech, who is this same character with the plus of being attractive (but still with no luck, and even less of a clue). Also see Prince Charming Wannabe, for another character who sees himself as the man of someone's dreams, but ignores or is oblivious to the fact that she wants nothing to do with him. See also Looking for Love in All the Wrong Places — the two character types complement each other and sometimes overlap. See Lousy Lovers Are Losers for the character does have sex but is incredibly bad at it.


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  • The Brad in this Smirnoff Ice Triple Black commercial.
  • The dancing guy at the 12 second mark in this Farmers Insurance commercial.
  • M&M's: Blue is this. He thinks he's a cool ladies' man, but so far no girl has shown interest in him beyond wanting to eat him.

    Anime & Manga 
  • Saori of Girls und Panzer is a rare female example. She'd have an Urban Legend Love Life if anyone believed her for more than five minutes. So infamous is she for her failed attempts that the girls of Rabbit Team once jested that she has a more successful "romance" with the Panzer.
  • Jenos Hazard of Black Cat. Most of his appearances show him striking out while hitting on women, and his official character profile even remarks about how his success rate with picking up women is way lower than you'd assume of someone with his assets (which include good looks, a snazzy suit, and a prominent position in one of the most powerful organizations in the world).
  • Finral from Black Clover. It's stated in his introduction that his liking for women interferes with his work. However, he hasn't found a girlfriend yet. When Finral goes on a triple date, with Asta and Luck tagging along, he soon realizes how big of a mistake it was to bring them. This behavior came about from realizing that his brother would become the head of his family and be forced to marry Finnes instead of being married to her himself despite their mutual attraction. Thanks to a major tongue lashing from his brother, he tries to stop his habitual advances on women to become worthy of being Finnes's fiancé again, turning him into a Nervous Wreck around attractive women when trying not to cheat on her anymore.
  • Bleach: Keigo loves women, especially if they have large breasts. He's never successful in his attempts to attract a single one.
  • In the Disney dub of Castle in the Sky, Papa (the engineer on the Tiger Moth) gets to say this in a one-liner cut from the 2010 DVD release:
    "I need someone who's mechanically minded, not some half-baked, swashbuckling Casanova wannabe!"
  • Sunohara from CLANNAD has a bit of this. It is not helped by Tomoya and occasionally Kyou taking advantage of his gullibility and tricking him into thinking a girl is interested in him.
  • Girls Bravo: Fukuyama plays the trope straight and subverts it at the same time:
    • Kirie and Koyomi, especially, want nothing to do with him because of how lewdly and shamelessly he comes onto them. And has a habit of barging into Kirie's class to flip up her skirt and grope her, right before she flattens him for it.
    • On the other hand, the women of Seiren love him for it. They're just as horny as he is and gladly strip themselves naked so he can fondle them to his heart's content (and theirs).
  • Takamura Mamoru from Hajime no Ippo. The most infamous incident being him getting rejected in front of a Love Hotel. To make matters worse, a Paparazzi just happened to be there with a camera ready. Cue Amusing Injuries from Team Dad Kamogawa and horrified reactions from other boxers.
  • Hetalia: Axis Powers:
    • France is somewhere between this and the The Casanova. None of the other nations are interested in his advances, but he apparently has had lovers, and he does manage to successfully molest (or at least strip) several of the other nations.
    • Could also apply to Italy, as he's frequently seen flirting with women, yet still hasn't done it. (Or could be a Chivalrous Pervert).
  • Kir from King of Bandit Jing. Interestingly, most of the time, the girls rejected him not because he's a bird, (sometimes they even think that his attempts to woo them are endearing) but because they usually have emotional baggage need to be resolved.
  • Shimada from My Monster Secret not only fails to seduce any lady, he also has rotten luck that borders on karmic with the ones he hits on. Ryou, his "girlfriend", is notably... a guy in a female Mobile-Suit Human, who is also a Casanova Wannabe. Later on, he tries to hit on his young and beautiful new teacher Ryokuenzaka Yumi; who turns out to be a giant male vampire in a female disguise. He's also a fan of Shiho, who switches genders when she sees the moon. Shima doesn't suspect any of that.
  • One Piece: Sanji never has gotten and most likely never will get lucky with any of the girls he's wooed so far in the story. Considering Word of God definitively states No Hugging, No Kissing for the main crew, of which Sanji is a part, of course he will always fail when it comes to the ladies. Early on in his characterization, he actually was capable of attracting women; that's just deteriorated over time. In this case, Failure Is the Only Option. The Totto Land arc gives him an actual Love Interest except that she's actually planning to murder him, and even though she eventually falls in love with him for real, she has to be left behind at the end of the arc.
  • Brock and Ash's Oshawott from Pokémon: The Series. Fortunately for Brock, he usually has someone, usually Misty, Max, or his Croagunk, to pull him away from a girl he hits on before he makes a complete fool of himself.
  • Tatewaki Kuno of Ranma ½ straddles the line between this and Handsome Lech. 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 (most commonly 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, as in one story where he loses his memories, after he takes "the pigtailed girl" to an island alone with him, he starts lustfully chasing her around the island.
  • Space Dandy from, well, Space☆Dandy, spends much of his time thinking about beautiful women and trying to flirt with them. The thing is that said beautiful women are almost all far smarter, more skilled, and superior in combat than he is. That being said, he does manage to score a victory every now and then when Space Dandy's heart is in the right place. Meow would be one too if he hadn't already given up, content with taking voyeuristic photographs and browsing porn online.
  • Ataru Moroboshi from Urusei Yatsura has a face only a mother could love (and even she sometimes regrets having him), and the worst luck possible. Nevertheless, he is always ready to ask a random girl off the street for her address and phone number. This despite having an alien beauty (who has electric powers and is deathly jealous, to boot - just do the math) for a fiancée. His main trait, though, is Cosmic Plaything considering how much he pays for this. ironically, his archrival Shutaro Mendo is a Handsome Lech — one whom Ataru's original girlfriend, Shinobu Miyake, dumped Ataru for on first sight and proceeded to chase him for most of the series.

    Comic Books 
  • From Superman: WGBS and Daily Planet sports reporter Steve Lombard, especially in All-Star Superman.
  • Viz (the comic book, not the Anime distributor) gives us Sid the Sexist, who, while not wearing a leisure suit, is very much a virgin despite his claims to the contrary and his attempts to change that situation. His friends could also possibly come under the same category - while they have occasionally been shown having success with women, usually they appear to look up to Sid for his 'studliness'. One strip even featured the brother of one of Sid's friends, who wore a leisure suit and claimed to be a massive hit with the ladies. Sid attempts to one-up him by getting several love bites - with the aid of a bicycle pump. He is, of course, caught and mocked by his friends. But then the last panel shows the friend's brother, alone in a tiny bedroom, doing the same trick, surrounded by porn magazines, used tissues, inflatable dolls, and other sexual paraphernalia, making him possibly the only character to have ever been made to look even more pathetic and lonely than Sid in the strip.
  • The Flash: Though not his defining trait, Wally West was known to be a skirt-chaser when he 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 Magnetic Hero, he often succeeded in being Amicable Exes after the break-up), his immaturity was a constant turn-off. A big contributing factor to his Character Development was him meeting Linda Park, who after initially disliking one another became Fire-Forged Friends and he developed a Single-Target Sexuality pretty much as soon as they started dating.

    Comic Strips 
  • Nate Wright, the titular character from Big Nate is a KidAnova Wannabe. His combination of utter cluelessness and unwaning self-confidence when it comes to girls is a central theme in the comic.
  • Steve Dallas from Bloom County, who apparently thinks a box of obscenely-shaped chocolates will win a woman's heart (or at least get her to sleep with him). Though apparently he did eventually have sex with a woman, as his son Augie shows up in the sequel comic Opus.
  • "Spit" Murphy from Footrot Flats.
  • Jon from Garfield, although he finally had success with Liz, after 28 years.
  • Jonny Kizinski from Knights of the Dinner Table. Jonny is actually married, but that doesn't stop him from hitting on every female gamer to cross his path (and failing miserably).
  • Dean the pig from Liberty Meadows, where all the animals are anthropopathic, if not anthropomorphic.
  • Snoopy's "Joe Cool" character in Peanuts fancies himself a chic magnet, but this is doubtful.
  • Jokke from Pondus flip-flopped between this and Kavorka Man, mostly with huge ugly women. (Said women have become somewhat of a staple of the series) After he got into a steady relationship, this role went to Ivar and Hugo, a pair of bottle cap collectors who never get out of their bus driver uniforms. The biggest difference between them and Jokke is that they never get lucky.
  • One of Rudi's buddies is the most obnoxious one you can think of. Sometimes, however, he is successful.
  • Fillmore from Sherman's Lagoon goes to mating season every year at Ascension Island and consistently fails horribly.

    Fan Works 
  • The Bolt Chronicles: 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:
      The little white mutt also fancied himself quite a ladies' man, and while he had been the cause of several unwanted surprise litters in the area, his brusque and truculent manner didn't make him universally popular with the opposite sex.
    • 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.
  • The LDD-fanfic, Bridge to Terabithia 2: The Last Time (taking place six years after the original story, where Jess and Leslie are teenagers at this point) has an appearance from Jess' obnoxious cousin, Nicholas, who shows up during the Thanksgiving chapter. His first line have him bragging to Jess about his (unseen, most likely non-existent) girlfriend, and when Leslie shows up at Jess' place as a guest, Nicholas then brags about how he'll "make Leslie fawn over him by the end of the day". Needless to say, Jess is not amused.
  • Code Geass: Paladins of Voltron: Though Rivalz obviously likes Milly, he'll hit on anything if it's on two legs and cute. This actually gets his Lion stolen at one point when a female bounty hunter plays Rivalz like a fiddle and handcuffs him to a tree.
  • In Faded Blue, Rose Quartz has a tendency to flirt with most humans she meets, trying to kindle something with Greg and then flirting with Priyanka and Doug. Granted, it is very likely that she does not even know that she does it half the time due to having No Social Skills with humans despite her charisma.
  • The Many Dates of Danny Fenton, a Danny Phantom fanfic: Even when girls give Tuck a chance despite his misleading profile, his lame come-ons cause them to leave.
  • In Touhou fanmade series Wiccan & Swordsgirl, Hiraku Okami has a habit of hitting on almost every named female character, youkai or not, ranged from Hong Meiling, Sakuya, and even Keine. Obviously, it ended badly. However, his legitimate love interest is Momiji Inubashiri, a fellow wolf tengu soldier. The feeling is mutual.
  • Total Drama All-Stars Rewrite: Lightning shows signs of this in the season's Aftermath (which he never did in canon, although it fits his egotistical personality). He hits on both Bridgette and Leshawna, claiming no girl can resist him, but only succeeds in offending them (as well as Geoff and Harold).
  • In Two Spiders on a Web, an ordinary civilian hires Spider-Gwen 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 with a Flirtatious Smack on the Ass, but Gwen is having none of it and proceeds to web him up and leave.
  • Voyages of the Wild Sea Horse has "The Reefster", a barracuda fishman and member of the White Foam Pirates, a minor band of surfing-obsessed pirates who make small appearances during the Paradise portion of the story. He clearly thinks of himself as a great lady's man (and also a man's man — he's not picky) but his pick-up tactics come off as sleazy and his personality comes off as arrogant, entitled and self-absorbed. In one chapter, he hits on Harumi, then hits on Harumi's tiger-shark wotan girlfriend Miriam right in front of Harumi, suggests they have a threesome after they tell him they're together, and finally gets mad and calls Miriam a Category Traitor for turning him down when she refuses. At which point she smacks him across the room with her tail. The Reefster's own captain calls him an idiot and a pervert.

    Films — Live-Action 
  • Anchorman: The Legend of Ron Burgundy: Ron Burgundy. Though he does wind up getting the girl, then losing her, then getting her again. But the news team's attempts to woo Veronica fit pretty much exactly into this Trope, complete with leisure suits. Most of the characters Will Ferrell's played recently tend to be this. Oddly enough, this is a bit of a Zig-Zagging Trope for this movie. Only with Veronica is he a wannabe — with other women, he's aloof enough and famous enough that even his lamest lines work.
  • The Brady Bunch: Greg's Big Man on Campus character from the original, Flanderized and comically made into a complete loser who is totally oblivious that he is a loser.
  • Brain Donors: Roland T. Flakfizer talks a great game.
    "Please, call me what everyone else calls me: 'Your Royal Sex Machine.'"
  • Dawn of the Dead (2004): Bart the security guard. The Zombie Apocalypse is on, and all he can think about is how now he's missed the chance to have sex with a fat chick from Dairy Queen.
  • Dr. Minx: David fancies himself as a ladies' man, but his technique is so over-the-top macho and off-putting that Carol all but throws him out of her house. And when Carol falls for his Nice Guy best friend Brian, David decides that she must be sick in the head as that is the only way he can rationalise a woman preferring Brian over him.
  • Fanboys: Harold "Hutch" Hutchison.
  • Hall Pass: Has two wives giving their husbands a free week to have sex outside of the marriage. The two are convinced that they can pick up any woman they want...and fail.
  • Jurassic World: Owen. Barry hints that he's this in the video game, but one of his lines from the movie pretty much confirms this when he says this to Claire:
    You want a consult here or in my bungalow?
  • Lizzie Borden's Revenge: Bobby's persona. Running a sleazy website and constantly coming on to when. He asks Dee if she wants to get something off her chest, and suggests her bra, while they are being stalked by a supernatural Spree Killer. It turns out he is actually gay, and this is just an act for his mother's benefit.
  • Love Actually: Colin Frissell (Kris Marshall). His friend Tony calls him "a lonely, ugly asshole" but Colin is convinced that he's a "god of sex", and the problem is that British women are too stuck-up — if he went to America, he'd have a girlfriend "instantly". Subverted when it turns out he's right, to an absurd degree.
  • Mabel's Strange Predicament: Charlie Chaplin's Tramp character (the second film of Chaplin's career and the first in which he dressed up as the Tramp). In this one, he's a drunken hotel guest who makes an ass of himself by hitting on all the women in the lobby and chasing poor Mabel Normand around.
  • The Mask: The Mask is sweet, kind, polite and nice like Stanley Ipkiss but is too strong towards the woman they love Tina but he does win her over eventually because of him being a Nice Guy to her in the park despite doing it somewhat sleazy at first which he got better at it.
  • Middle of the Night: Lockman, a 60-year-old Dirty Old Man who brags about all the "tootsies" he's regularly bedding. Eventually, he shamefully admits that he's been impotent for two years.
  • The Private Life of Don Juan: Features Rodrigo, a young man who is trying to copy the real Don Juan but can't even manage to get over a lady's balcony without tripping. The first time he's challenged to a duel by a jealous husband, he's killed.
  • Slap Shot: Moe. Every single thing he says has to do with sex and he has pictures from nudie mags taped to his locker. Yet he is never seen with a single woman at any point in the film. The weird goalie with a thick Quebec accent does better than Moe.
  • The Three Musketeers (2011): Subverted with D'Artangan. When he first encounters Constance - who he doesn't know is Queen Anne's lady-in-waiting and therefore notably higher up the social strata - she sees right through his cheesy attempts to woo her. It's only after he proves his passion to be a Musketeer and puts his life on the line - both for her and for France - that she understands the depths of his devotion and lets him in.
  • Troll: Peter Dickinson is a middle-aged bachelor who's biggest interest in life is bedding women. In the film he does manage to bring an attractive lady home with him. However, the next morning it's clear she did not enjoy the experience and she storms out of his apartment when he asks her to make breakfast.
  • The View Askewniverse: Jay.

  • Marco from Animorphs is a particularly young version of this.
  • Diary of a Wimpy Kid: Greg often attempts to get with various girls, but he's so bad at it that it ends up that the girls in question never even realize he exists or he ends up looking like a perverted loser in front of them.
  • Emil Sinclair from Hermann Hesse's novel Demian fits this, as he talks the talk, but actually the only move he made was a crush on a storekeeper. That happened during his school days. Later, he did have a brief romance... to his best friend Max Demian's mom. They actually even kissed, but that's it.
  • Carlos Ramirez from The Dresden Files fits this. He's a young, somewhat cocky, warden who is constantly bragging about his sexual exploits. None of which have ever happened, seeing that he's a virgin. Revealed hilariously by Lara Raith.
  • Masomi Kida from Durarara!!. His attempts at wooing women fail to the point where even his partner Mikado lampshades his failures. However, he stops when he gets back with his former girlfriend, Saki Miyajima.
  • Taniguchi, one of Those Two Guys in Haruhi Suzumiya, fancies himself a ladies' man but it's made very obvious that he's not.
    Taniguchi: "We find a couple of ladies dressed up all casual-like... make with the chit-chat and it's ON! It's a technique I've developed over years of experience!"
    Kyon (in narration, but possibly aloud): "What good is your experience when your success rate is zero?!"
  • Is This A Zombie? has Orito, who thinks he's the epitome of the ladies' man and is completely oblivious to the fact that everybody thinks he's an annoying and creepy geek.
  • Keeper of the Lost Cities: Dex's little brother Lex tries to act like a young ladies' man, only for his father to block him and give him a talking-to.
    "He's just jealous," the boy told Biana. "He knows the ladies like me better."
    "Okay," Kesler said, grabbing the boy's arm before he could wrap it around Biana's waist. "Looks like we need to have another talk about appropriate behavior around girls, Lex. Rule number one—we do not touch them without their permission.
  • No Beast So Fierce: Max's friend L&L Red used to be The Casanova for real, but years of drug use has destroyed his good looks and left him a husk of his former self. The few times he's shown flirting with women, he strikes out invariably.
  • In Prophecy Approved Companion the bard character is supposed to be a genuine casanova. Unfortunately, the game allows the player to rename companions and, since they found the bard in the Absurdly-Spacious Sewer he's renamed to Sewer Bard. Things only go downhill from there.
  • In Tim Dorsey's Serge Storms series, 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.
  • Mario Bianchi in Skippy Dies constantly brags about his prowess with the ladies, but is never seen with any. To be fair, he does go to an all-male boarding school, but the one time he has the opportunity to meet women, he strikes out completely.
  • In Scavenger Alliance, Luther assumes Blaze will accept his offer of marriage, despite making it clear that he's only interested in marrying her because he assumes that marrying Donnell's daughter will get him the position as Deputy. He treats the marriage as a done deal, based on a crush Blaze had on him a couple of years earlier. He finally backs off when Blaze threatens to paint her refusal on the wall of Reception in large letters for the whole Alliance to see.
  • This Side of Paradise: Kerry Holiday has tried every single trick in the book to try getting a girl but fails, including when a St. Timothy girl cut out the "My God" from a "My God, how I love you" in a letter he wrote to her and showed the rest of the letter in the school. He even asks Amory, who has been in successful relationships, how to win a girl over but later accepts he likely won't be winning one over.
  • Tides of Protomis: Has Kazimir. Who is prone to try to get any "Babes" that came his way. with mostly bad results. However, this ends up being phased out entirley as Miyamoto Junko joins the allied cast.

    Live-Action TV 
  • In Auction Kings, Jamie loves to make passes at Cindy. She is generally unimpressed.
  • In Smallville, Bart, who hit on Chloe twice, with the second time failing especially spectacularly.
  • Jay on Herman's Head, but Jay is also Looking for Love in All the Wrong Places.
  • Larry Dallas of Three's Company is named Larry and may even be the inspiration for the computer game, but had too much (read: more than one) actual success with the ladies to really exemplify the trope. Mr. Furley probably qualifies though.
  • Howard Wolowitz from The Big Bang Theory embodies this trope to a full 100%, until he meets Bernadette, at which point he drops the suave guy act, which paid off as they eventually become a Happily Married Beta Couple.
  • Herb Tarlek of WKRP in Cincinnati is on the fringe of Larry-dom since he's married and has kids. However, he does have the bad suit, attitude, and lack of success necessary to play the part.
  • The Young Ones: Mike, the self-proclaimed stud, was revealed in one episode to be a virgin. But given the show's Negative Continuity it's hard to say whether that really counts.
  • Murdock tries this in an episode of The A-Team when Face briefly leaves the team. Keyword, tries.
  • The title character of Banacek wasn't by any means a dud with girls, but he was often snubbed by dames he attempted to hit on.
  • Get Smart: Max somehow thinks that he's a James Bond-type playboy.
  • Taxi: Louie will attempt to flirt at women to no avail, especially with Elaine.
  • The Todd from Scrubs may be the ultimate Casanova Wannabe, especially after he comes to terms with his bisexuality. And possible anything-sexuality:
    The Todd: Whoa, these are hot. [referring to two pieces of broccoli]
    Turk: Please tell me you mean temperature-wise, because there's no way you could find broccoli sexy.
    The Todd: Oh yeah, temperature-wise... and miniature-green-boobs-wise! [rubs his face between the two heads of broccoli]
    • Todd regularly boasts a great track record and hits on or makes innuendo at anything that moves. When pressed by The Janitor with "God is watching. How many times have you had sex in the last year?", he confesses none. Many women at Sacred Heart claim to have never slept with the Todd despite reputation, but they have proven to be extremely defensive about the idea to the point of suspicion.
      Todd: Hey, Lisa. I heard you lied and said we didn't do it. Admit it. We doinked.
      Lisa: I was sad because my dad died.
      Todd: I wasn't.
  • Bud Bundy from Married... with Children.
    • This is debatable, however. As Ted McGinley points out in the Reunion Special: "Bud was pretty successful because he had the greatest-looking girls, week to week." This just isn't acknowledged in the series because of its Negative Continuity. It's just his success rate that's low, which isn't surprising considering he tries to get some in every episode.
    • In an episode where Al and Peggy split up, Al and his buddies tried to hit the club scene. Al got a makeover and became the definition of Casanova Wannabe. He also got a prosthetic ass.
    • However, when he gets the opportunity he always turns it down including a "shoe groupie".
  • Julian Bashir of Star Trek: Deep Space Nine.
    • He has had notable success, perhaps too much to be considered the Casanova Wannabe; besides the Daxii, there's a long-but-not-deep relationship with Leeta, and briefer affairs with the mute genius girl and that weightless chick.
    • Dr. Zimmerman, inventor of the Holodoc, certainly qualifies in his appearance on Deep Space Nine.
  • Jay from the British cult sitcom The Inbetweeners, who makes near-constant boasts about his sexual expertise despite his obvious virginity. Jay is a bit of a vague case, though, as he rarely ever talks to girls. He apparently prefers to brag to his male friends about his exploits instead. But when he does try to chat up girls, they don't usually seem interested (except for Chloe).
    • Will alternates between this and Kavorka Man. He does score with Charlotte—the school's most popular girl—and his hot, former babysitter, but he screws up before any of them manages to take his virginity. And when he tries to pull a nice and down-to-earth girl, Lauren, he fails spectacularly, especially by trying to imitate Yoda. He doesn't have much luck with Rachel either as he, according to the guy Rachel flirts with instead, "talks like they do in old movies".
  • Subverted on Burn Notice—even though Sam acts, dresses, and looks like an archetypal Casanova Wannabe, he's actually successful with the ladies, although he uses his charms to woo rich divorced housewives who buy him nice stuff.
  • The two guys that Chris Kattan and Will Ferrell played in the Butabi Brothers sketches on Saturday Night Live, named Doug and Steve respectively in the movie adaptation, A Night at the Roxbury. Other examples of a Casanova Wannabe on Saturday Night Live include:
    • Christopher Walken's "The Continental", a parody of a 1950s-era New York local TV show.
    • Chris Parnell's "Merv the Perv" (who also had a brother played by Johnny Knoxville named "Irv the Perv")
    • The Woman Watchers (played by frequent host Tom Hanks and cast member Jon Lovitz, from the mid-1980s SNL)
    • The original "Two Wild And Crazy Guys!" (also played by a cast member and a frequent SNL host, only this time, it's Dan Aykroyd [the cast member] and Steve Martin [the frequent host]), compounded by them being Funny Foreigners with a middling grasp on the English language.
  • Buffy the Vampire Slayer:
    • Subverted with Larry (hmm, Shout-Out?), who displays this behavior for a while, only to have it revealed in "Phases" that it's all an act, and he's actually gay. After he comes out to Xander (in private) he drops the act, though he is never seen to come out publicly on-screen.
    • Buffy also toys with the idea in "Teacher's Pet"; one of the victims is very embarrassed when told that the mantis only attacks virgins.
  • Yo soy Betty, la fea provides us with two: Nicolas Mora, nerd extraordinaire and self-assumed ugly, who nonetheless still tries to hit on pretty girls and constantly woo Patricia Fernandez; and Freddy, the motorized messenger of Ecomoda, who, while better-looking (and better-dressed) than Nicolas, still exudes a big "loser" aura. Freddy manages to have an on-off relationship with Aura Maria, the hot receptionist of the company, but he inadvertently and constantly ruins any progress he does with her thanks to his misguided flirting towards the models who flood the place.
  • Kirk St. Moritz (a.k.a. Eric Morris) from Dear John.
  • On How I Met Your Mother Barney flips back and forth between this and The Casanova, with a bit of Handsome Lech thrown in. On the one hand, he is quite handsome, dresses in legitimately stylish suits and the notches on his bedpost are well into the triple digits. However, a lot of his pickup attempts can be pretty darn cheesy, it's clear that he's not always truthful about his sexual conquests, and, since the entire series is a story told by a potentially Unreliable Narrator, separating the lies from the truth isn't so easy.
    • At one point, Marshall actually calculates that, given the number of women Barney's slept with, compared to the sheer number of women he hits on, his success rate is actually only a little over 1%, despite having slept with more people than the rest of the main characters combined.
  • Tom Haverford from Parks and Recreation is a special case. In the first season, he tells the documentary crew that he and his wife have an open marriage and that they're both disappointed he's not a more successful adulterer. His utter failures to pick up women are often shown. In the second season, Ron learns that Tom's wife is Canadian, and only married him to stay in the country.
    • His buddy Jean-Ralphio qualifies as well.
  • Friends: Played with with Chandler. He teases Ross who is desperate to get married again, envies Joey for being The Casanova, tries for a few one-night stands himself, and has Commitment Issues. However, even early episodes have him ending no-strings-attached sex because he wants a relationship, and trying to keep a steady girlfriend. Most of his Commitment Issues stem from a fear of being hurt, rather than wanting to play the board, and he's ten times happier after falling in love with Monica and being the first of the guys to get married (permanently, anyway).
  • Jackson Stewart of Hannah Montana has tried every cheesy pickup line and hare-brained scheme in the book to get girls. Mild subversion in that he has a fair amount of success, but rarely makes it past the first date.
  • Evan Lawson of Royal Pains is an inveterate Casanova Wannabe.
  • Jerry Robinson of The Bob Newhart Show is kind of a mild version of this.
  • Stanley Tweedle of Lexx.
  • Henry and Dave compete for the title in Drop the Dead Donkey. Henry is closer, though, probably because he turns 60 during the series' run and Dave is supposed to be in his early-to-mid thirties.
  • Richard Richard in Bottom is a particularly obnoxious example.
  • Mr. Lucas from Are You Being Served? fits this trope. Despite being allegedly good-looking and always claiming to be lucky with the ladies, he never seems to have much luck with them on the actual show.
  • Nathan from Misfits tries to chat up virtually every girl he meets, with very limited success. And when it does work, something usually goes spectacularly, mind-bogglingly wrong—e.g. one of his love interests is revealed to be an 82-year-old in disguise, mid-coitus. But most girls just seem disgusted with him on sight and immediately ignore or reject him. That said, he's undoubtedly only a Casanova Wannabe in-universe—among the fans he's easily the most popular and lusted-after character on the show, despite his obnoxious personality.
  • Pierce from Community obnoxious attempts to hit on Shirley and to a lesser extent other female students. However, the audience is shown he is a skilled seducer when he needs to be.
  • Whenever Winston Rothchild plays the Possum Lodge Word Game on The Red Green Show, Red gets the correct answer out of him by mentioning one of his past dates. Winston's words, for the record, are usually along the lines of "disaster" (in fact, that was one of his words).
  • Ethan, Benny, and Rory from My Babysitter's a Vampire and HOW. Every episode has multiple examples of their romantic failure. (Though in his defense Ethan is nowhere near as bad as Benny, and Benny in turn isn't as bad as Rory.)
  • Bobby Lee’s character Tank, from MADtv (1995), is a clear example. Despite his many elaborate attempts to score with women, he remains a virgin.
  • Paramedic John Gage on Emergency! definitely qualifies. He considers himself a ladies' man, but the ladies usually think the exact opposite, and any time Gage tries to give advice on women to his partner DeSoto, the advice turns out to be the exact wrong thing to do. Rarely do we see him actually have a successful date, which is pretty hilarious considering he's a rather attractive young man. He often gets teased for it by Fireman Chet Kelly, although Kelly doesn't seem to do any better with women.
  • Cabbage Head on The Kids in the Hall.
  • Dwayne Schneider on One Day at a Time.
  • Scandal: Stephen, though he seems to have mostly settled down. He still has an interesting past.
  • A Mr. Show sketch, has Lyle, one of the scientists living in the biosphere. On New Year's Eve, he tries asking out all the women, who all reject him. Seems like he's gonna be alone on New Year's . . . until he gets a visit from his step-Fairy Godmother.
  • It's Always Sunny in Philadelphia: Zig-Zagged with Dennis Reynolds. Sometimes he's good with the ladies, other times he's this trope. Both reactions are justified because he has been able to function socially more than the rest of the gang which isn't saying much. However, he also has been shown to be the most depraved member of the gang and has little understanding of human relationships. He also gets Mistaken for Gay when he hits on a married woman by gossiping about her husband and wearing make-up and a girdle. On a dating website, he gets 0 Stars. It says something when his two friends Mac and Charlie, a fake macho Armored Closet Gay and an illiterate idiot with No Indoor Voice who kills rats for a living, get higher ratings than him.
  • In My Hero (2000), Dr. Crispin gives the impression that he's had loads of women but admits in "A Day to Remember" that he's actually a virgin, and while he apparently lost his virginity later, considering that it was to a woman at least the age of Janet's mother who had false teeth while he was utterly drunk, it's questionable if he would be able to or want to remember it.
  • Jerome, one of the many characters Martin Lawrence played on his television series, is a man in his late 40s who is going through a major mid-life crisis. He believes himself to be the ultimate player and that all the women want him, especially Martin's wife, Gina. It's all in his head, however, and a lot of hilarity ensues. He even has his own theme song.
  • Cobra Kai: Hawk, early in season 3, plans to have "a full rotation of girls by midterm. However, his attempts to flirt are promptly shut down, as the girls in question know about his chronic bedwetting, and they end up showing more interest in Demetri instead.
  • My Left Nut: Tommy acts like he's a player and a Chick Magnet, but his perverted way of acting only repulses girls. Siobhan later explicitly says she only went out with him on a Double Date because Rachael wanted to go out with his Best Friend Mick, and she doesn't actually like Tommy at all.
  • Pataclaun: Tony likes to think of himself as a great ladies' man, capable of landing a gig as a big soap opera male lead. However, we never see him in a succesful relationship, and Wendy always ignores him whenever he tries to woo her.
  • She-Hulk: Attorney at Law: Jen Walters' former co-worker Dennis Bukowski is convinced that every single woman he sees is a potential romantic partner and seems oblivious to the fact that every woman who hears this reacts with open disgust. He refuses to have Mallory Book represent him in court because he thinks they could end up dating, even though it later turns out Mallory is Happily Married. He's convinced Jen's paralegal Nikki has a crush on him when Nikki openly admits to fantasizing about killing him.

  • Bliss End Of Gods: Gan Luo tries to seduce Bliss in an early chapter and is rejected, and a special chapter is all about him going on several dates with women who likewise reject him.

  • The Creep by The Lonely Island has several.
    • Also Andy Samberg and Justin Timberlake in the Dick in a Box, Motherlover, and Threeway videos, right up to the polyester suits and gold neck chains.
    • "We Need Love" is a brutal parody of this trope.
  • Sonic Youth's "Swimsuit Issue" is about a guy from Geffen Records who annoyed the band by acting like this.
  • The title character of "My Name Is Eugene" by Crazy Joe & the Variable Speed Band.
  • Jon Lajoie:
    • It's unclear how successful MC Vagina is at winning over women, but his awful singing, blatant sexism, and laughably bad pickup lines (he considers a song for the ladies to be one entitled "Show Me Your Genitals") would probably doom him in any sane world. Notably, despite his claims of having wooed women around the world with his twenty-five-inch penis, the only time he's ever seen onscreen with women is in "Very Super Famous," and they were decidedly not head-over-heels.
    • From "WTF Collective," the rather aptly named "MC Cockblocks Himself":
    Crawl in a hot tub with a bottle of champagne
    By the way, I have a girlfriend, and I think I may have AIDS. (Where you going?)
  • "Ma quale idea" by Pino D'Angiò is a tongue-in-cheek italo-disco ballad sang in the perspective of a bold but ultimately unsuccessful ladies' man; the chorus of the song even targets the singer's ineptitude at wooing women.
  • Red Vox's "There She Goes" is a lighthearted account of a man who keeps trying to pick up girls, only for them to walk out on him in the morning. He starts with someone he picked up at an old bar, gets catfished by someone he met through a dating/hookup app, and finally ends up settling for some porn he finds in the trash.

    Pro Wrestling 
  • WWE tried to give Dean Malenko a ladies' man gimmick after the Radicalz broke up, but he was too short and too old to be believable in the role.
  • Joey Ryan's most notable gimmick was that of sleazy lecherous creep with a Pornstache and Carpet of Virility who acted like he was pulled right out of the '70s.
  • Austin Aries told a fan heckling him at ROH The Final Showdown that if he wanted her mouth open he'd have dropped his pants. That was before he took on the (admittedly Lighter and Softer) "A Double, The Greatest Man Who Ever Lived" gimmick in Chikara.
  • Zack Ryder, a gullible, self-absorbed, outspoken loser who will often pick up and lose a WWE 'Diva' escort over the course of a show.
  • "Prince" "Wonderful" Xander has probably always had traces of this trope about him but it really went to his head in the World Wrestling League.
  • After his CMLL debut, Matt Taven proclaimed he had come to the land of trios in preparation for winning the ROH Six Man Tag Tournament at Final Battle, adding
    "There can only be one first, ask your girlfriend."
  • Cam Stewart wants everyone of you to subscribe to his Only Fans page, but outside of his opponents, who he tries to get to agree to subscribe with submission holds, he most heavily pushes himself on the ladies, stuffing his trunks and dancing seductively for them.

  • Martin/Molloy: Haughty Mick was a character played by Molloy who spoke in Ye Olde Butcherede Englishe and offered his 'seduction tips' to the listeners. ..although, he proved his tips to be unsuccessful as his bad pick-up lines always got a knock back from the damsels/wenches.
  • Nebulous: Rory Lawson claims to be the 'ladies' man' of the team, but when his only two depicted successes were with a drunk Paula Breeze and a hippie 'Lindavidual' at Woodstock, it's hard to take his claims seriously.

  • The Dark Dragon, Simon's split personality from Dawn of a New Age: Oldport Blues, believes himself to be sexy and suave. The reality is that his lecherous personality is a big turn-off to any girl that interacts with him.

  • The Cashier in The Most Happy Fella unsubtly announces his eligibility to the waitresses. The heroine makes her first entrance in the show by rejecting his advances violently.

    Video Games 
  • Agarest Senki gives us Winfield and Thoma. Winfield is a textbook case of this trope. Thoma however actually has a crapton of game and earns the ladies company. Too bad Winfield taught him how to treat a woman which leads to Thoma starting off strong then halfway becoming like Winfield.
    • To put this into perspective Thoma said the wrong thing TWICE to a Tsundere. In the same sentence. While she told him to buzz off. He still convinced her to hang out with him yet Winfield's brainwashing led to another sexual comment. He manages to leave unscathed due to turning her anger into exasperation. Thoma got game, but his teacher just programmed him not to use it consistently.
  • Baldur's Gate II:
    • An elf called Salvanas, who can be found in a bar, is a minor character whose only function is to hit on every female party member that talks to him (except Imoen, who was added at the last moment). Salvanas flirts so blatantly shamelessly that he's inevitably angrily rejected. The only one interested is a temporary female Edwina—but after Salvanas's verbal slip she gets angry and kills the poor elf. If a female player character chooses not to reject him, Salvanas gets scared and runs away.
    • A wizard Edwin hits on some female party members (including Mazzy the halfling!) and likes to talk about many concubines he left gasping after his erotic onslaught. In truth... well, it appears that in Athkatla he's had a fling with a barmaid, who finds him very cute.
  • Baldur's Gate III: Charismatic Folk Hero warlock Wyll falls into this, as he's ballsy enough to try to flirt with Lae'zel and Shadowheart at the same time, and moves onto the Player Character after getting rebuffed. If neither are romanced he does get lucky with Lae'zel, although she's not too impressed with his performance. If chosen as the Player Character however, he's much more successful.
  • Ringabel in Bravely Default hits on every woman he encounters and manages to annoy everyone around him in the process, including most of the women he tries to flirt with. The other members of the party put up with him because he's the only one who can pilot their airship. Played with in that only major female characters, the ones with names, react to him this way, and he has absolutely ridiculous amounts of success with minor female characters. He was extremely successful manipulating the hair dye saleswoman for information before Edea ruined it, and he's implied to have dated at least a dozen women offscreen, sometimes multiple at the same time.
  • Dota 2 has Batrider, who has specific responses for every single woman in the game. He even thinks about hitting on the Broodmother, who is a Giant Spider...
    Batrider: Broodmother, if you weren't already— ugh, never mind!
  • Dragon Age: Origins: Oghren imagines himself as being quite the ladies' man, though most of the females he hits on find him utterly repulsive. He was married, though his first wife left him and then fell in love with another woman. He then started up a relationship with Felsi, who was quite a looker ... which he ruins by impulsively joining the Gray Wardens after she gets pregnant. In truth, there is some hint that Oghren's lecherous behaviour is a cover for his crippling insecurities. If his personal quest is completed in Awakening and he has a high approval at the end of the game, the Gray Warden helps him break out of this behavior and be more responsible toward Felsi and their child.
  • Frank Barnes from Faust: The Seven Games of the Soul idolized the real Casanova, and his frustration at not being able to succeed at wooing women led him to make his deal with Mephistopheles. A letter from a woman responding to Frank can be found where she points out that the real Casanova was an adventurer, soldier, and diplomat, which made him an interesting person to be around, while Frank put his artistic talent off to the side in favor of focusing on pursuing women.
  • "Big" Tom from Fear Effect 2: Retro Helix. His 2 cut scenes consist of nothing but a bunch of lame come-ons directed at Hana, much to her disgust. One gets the feeling if they weren't in a crowded room, she'd have shot him.
  • As Locke and Sabin (his own twin brother!) note, Edgar of Final Fantasy VI is remarkably bad at flirting with women, no matter how often he does it. Given that he's a genius inventor who's also a beloved monarch and who insists on equal treatment between him and the rest of his subjects (not to mention being fairly physically fit and capable in a scrap), it leads one to wonder just how bad his flirting has to be that he's consistently striking out with the ladies.
  • Fire Emblem has quite a few:
  • Rock, a marriage candidate from Harvest Moon: Another Wonderful Life and its remake, Story of Seasons: A Wonderful Life, fits to a T, 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, even introducing himself as a “stud”) due to his outdated clothes and his odd personality, with his first romantic event with the player starting off by showing the closest person he has to a love interest running away from him. His complete lack of charisma is lampshaded by his own mother, who seriously questions your mental health should you pursue him, but tries desperately to pair you up anyway, telling you this is likely to be his only shot at love.
  • Zebruh Codakk in Hiveswap Friendsim isn't bad-looking, but his personality is so repulsive that players often consider the good ending of befriending him to be a bad thing.
  • Daxter from the Jak and Daxter series flirts with every attractive female he comes across, despite the fact that he's been turned into a three-foot-tall rodent. He seems to have grown out of it by Jak X, though it might just be because he finally has a girlfriend.
  • Of course, the eponymous Leisure Suit Larry, the former Trope Namer. He is basically a 40-year-old virgin in the first game, loses his virginity, but doesn't get a steady girlfriend. The general formula is Leisuresuit Larry manages to get the girl after going through many absurd hurdles at a game's end, only for the next game to begin with Larry getting dumped. For example, even after winning a contest to spend a week with the attractive woman captain at the end of one game, Larry has to bribe her with a large stock in oil hauling.
  • Ewan Devlin from Mercenaries 2: He believes that he's a smooth-talking Irish stallion, but as evidenced throughout the game, he often drives the girls away by talking their ears off, hitting them with a bust of the Big Bad, or by detonating something in the stockpile. His bio states that his successes with the ladies, such as they are, are attributable more to his relentlessness and complete lack of standards than anything else.
  • Junpei from Persona 3, who tries to make up for with sheer bravado what he utterly lacks in everything else when it comes to women. The ladies still aren't impressed.
  • Planescape: Torment: Morte does this as an act; he knows he'll never score for the obvious reasons and has nothing to lose, so he has fun with it.
  • Carlos Olivera from Resident Evil 3: Nemesis, famous for the memorably cheesy line "All the foxy ladies love my accent. It drives 'em craaaazy!" Jill, however, is already quite smitten with her task of avoiding a gruesome, horrible death, so depending on where she meets Carlos, she'll either shoot down his flirting or simply ignore it. The remake largely does away with this; he flirts a little with a still mostly non-receptive Jill early on, but he keeps it professional once it's become clear that she has more important things to worry about. Ironically enough, in the remake Jill over time does reciprocate his attraction to the extent she dreams about Carlos (a nightmare of being forced to kill him as he zombiefies).
  • Greg, one of the colonists in Space Colony. With the voice of a late-night radio personality and pick-up lines out of a Saturday Night Live sketch, Rick is an utter failure when it comes to women, even when compared to Mad Scientist Nicolai and Disco Dan Charles. He's a flagrant misogynist and is regarded with unmasked contempt by main character Venus; Even his official company profile paints him in an unflattering light. He's also one of the least useful colonists, having high standards for happiness and few strong skills. Greg, as it happens, appears to be based on a similar character from MADTV.
  • Super Robot Wars Advance: Axel Almer, when picked as the protagonist, is portrayed this way, flirting with every girl he sees and failing horribly every time. For example, when he is asked for his name by Sayaka Yumi, he tells her: "Maybe I'll remember my name if a beautiful girl like you kisses me".
    • This scene is replicated in a 4koma (when Axel and Sayaka are in their respective mechs) where Axel's mech is immediately blasted with a Rocket Punch out of nowhere.
  • Tales of Arise: The main reason Law repeatedly strikes out with the ladies is because they can tell he's a skirt chaser. Law will hit on virtually any girl within eyesight at the drop of a dime and even gets caught ogling Kisara twice. Which is also the reason he ultimately fails to get any closer to Rinwell, the one girl he has genuine feelings for.
  • Scout in the Team Fortress 2 official comics has a habit of Flexing Those Non-Biceps and flirting whenever a woman comes near, with zero success.
    • Interestingly, the one time he does get a chance to have sex (with a woman who hasn't seen a man beside her brother for twenty years), he backs out because he thinks the most common target of his flirtations, Miss Pauling, will like him better if he waits.
    • In Scout's own words, he's good at getting girls. What he's not good at is getting ladies. What's the difference? Well, this is what it looks like when Scout successfully picks up a girl:
      Scout: We both got buckets a' chicken. You wan' do it?
      Girl: [shrug] Eh, okay.
  • Valdis Story: Abyssal City has Vladyn, who has made "weak advances" on at least two of his crewmates, and tries it on again with the first female NPC he meets.
  • Final Fantasy Brave Exvius has Jake, the sixth party member to join in the plot, who hits on nearly every female he encounters. The barely legal engineer recruited by the party before him? Hits on her. The Really 700 Years Old archmage who appears to be a nine-year-old girl? Hits on her. The intelligent beastwoman who looks like a purple leopard (and is quadrupedal)? Hits on her. Discovers the millennia-old Leviathan that's hundreds of feet long is female? Hits on her. While he does eventually get his attention violently reciprocated by said engineer, he spends the greater part of two seasons striking out repeatedly. Ironically, the best chemistry he has (to the point of being a Fan-Preferred Couple in some cases) is with Nichol, the male tactician in the party.
  • Dragon Quest V: Optional Party Member Tuppence loves the ladies... the ladies just don't love him back.

    Visual Novels 
  • Dennis from Double Homework wants to be good with girls, but he never gets anywhere, no matter what he tries.

    Web Animation 
  • Despite his claims of prowess with the "lady-types", Strong Bad from Homestar Runner is definitely a Casanova Wannabe. In one e-mail, he slips and admits "I don't really know anything about the ladies either... I mean I do! I mean... WHGT! JGTH! YES I'M AWESOME!"
  • Helluva Boss: Chaz did successfully manage to seduce Moxxie and Millie in the past, by the time he makes an appearance he had burned both bridges spectacularly and both of them have nothing but contempt for him, no matter how hard he tries to win them over again, mainly the former. He only manages to do it with Blitzo and he only did it because he had sex with Moxxie and Millie, and even then Blitzo has nothing good to say about the experience.
  • This is a somewhat common character type in Object Shows. Examples include Dish Soap from Brawl for Object Palace, Coral from Object Explosion, and Grassy from Object Lockdown (Mostly in season 2).
  • Tucker from Red vs. Blue is a shining example of this trope. Unfortunately, the only women he sees on a regular basis are ruthless super soldiers who would kill you as soon as look at you. In fact, the only action he gets during the story is with Grif's promiscuous sister (or so he claims) and a Face Full of Alien Wing-Wong. (The latter, note, was only implied in hindsight by later events; at the time, everyone just thought Tucker was being beaten up.)
  • Rooster Teeth Animated Adventures portrays Chris Demarais as one, albeit as a more awkward one. While he has had successful dates, they don't seem to stick and he tends to find himself in more comically awkward dating mishaps.
    • "Chris's Great European Adventure" was his story of attending a raunchy German club and meeting a girl who playfully asked him to choke her as they were making out.
    • "Chris Strikes Out" was the story of Geoff and Michael witnessing Chris utterly fail to chat up a group of girls at a bar.
  • RWBY: Neptune has worked very hard to build a "cool dude" persona that includes hitting on every pretty girl he meets. Yang doesn't seem to notice his appreciation of her, Melanie and Miltia dismiss his approach entirely, but Weiss is impressed by him, much to Jaune's disbelief, as Neptune's moves on Weiss were actually the same as Jaune's. Neptune eventually admits to Jaune that he's hiding a completely dorky interior which puts him off pursuing Weiss more seriously. Jaune sets him straight, giving up his own attempt to woo Weiss in the process.
  • Neomutant from "TOME" is said on the TOME Character page to fancy himself as being charismatic. Though if his success with Flamegirl is anything to go off of, right down to scaring her straight into the arms of her love interest Alpha, he is far, far, far from successful as a Casanova.
  • Disco Bear from Happy Tree Friends is ostensibly the best example on the show, in case the first name didn't give it away already.

  • The Bug Pond: Flash.
  • In Commander Kitty, one of CK's main motivations for being a spacer is the prospect of wooing a princess or three. Later, when three exotic blue-furred android girls present themselves to him, he doesn't hesitate to follow along, even as they lead him into a room clearly marked "abbatoir"note .
  • Da Pukas: Portazo. He completely forgives Rumi for getting him and his friends exiled from their village for no reason other than the fact she has breasts. He also practically hits on anything that is female... except Ali...
  • Dean & Nala + Vinny has Sammy Chonkers, one of the house pets at a home hosting the titular trio. The chunky feline tries to pick up Nala by telling her that he has a stash of catnip if she is interested. Nala is definitely NOT interested.
  • Ears for Elves: Elon tries to follow Rolan's smooth style of talking to the elven women. They are not impressed.
  • El Goonish Shive: T.C., aka "The Playah", a student of Moperville North who works as a clerk at the movie theatre. As this trope makes him an acceptable target, he also works as a Butt-Monkey out of the main continuity.
  • Exterminatus Now: Eastwood, who regularly suffers great physical harm from hilariously crude attempts at hitting on anything with a skirt. Probably the reason why he has the biggest Porn Stash in the world. On such a scale that he's begun to acclimatize to pepper spray.
  • Femmegasm: June, in a rare female variety. Most people don't find monkeys with a large amount of distressingly long, thick body hair attractive, which means her attempts to get laid pretty much always end in rejection.
  • Forever 16: Aaron West, which gets kind of sad knowing that a theoretical Time Skip would have him still be this.
  • Full Frontal Nerdity: Lewis started out like this, with several comics devoted to him complaining about how poorly his dates tended to be and the other guys telling him that he should try focusing more on what the girl has to say and less on her bra size.
  • Homestuck:
    • Eridan Ampora is practically the classic example. Being from a naturally bisexual species, his options are a bit more widely ranging than most. Doesn't do him any good, though - not only is he rejected every time he tries but by the time he dies, he doesn't have any romantic relationships at all. Even his moirail has dumped him, fed up with his narcissism and his constant threats of genocide.
    • His dancestor Cronus is even sleazier and creepier, with No Sense of Personal Space. Cronus's example is made especially sad when he actually hits on Eridan. Even Eridan is able to immediately pin him as trash but ultimately accepts his advances out of very blatantly stated desperation.
    • Both are so pathetic they can't even form a blackrom with anyone. Everyone hates them, but in the "stay away from you creepy loser" way and not the "I love to hate you" way.
  • All the women in the Espionage theme of Irregular Webcomic! believe that James Stud is an annoying buffoon, however much he attempts James Bond's pick-up lines.
  • In Larp Trek, Will Riker's romantic streak is taken to the extreme.
  • While Rayne from Least I Could Do meets with great success, it's partially due to his "shotgun approach". One "Tao of Rayne" underscores this.
    The fool concerns himself with the 99 who say "no", while the wise man comforts himself with the one who says "yes".
  • From Little Gamers, "Did it hurt when you fell from heaven? Because your face is really fucked up."
  • In Misfile this trope is filled by Colin the Counter Guy in the local auto parts store.
  • Never Satisfied: Seiji will make advances on anyone, including Ana (a lesbian), Philomena (who literally just kicked Sylas out of her house), and a training dummy. He's gotten his ass handed to him for this behavior enough times that when he gets into a fight for a different reason, both his mother and Sylas readily believe that he "made a pass at a girl."
  • PvP's Robbie had all the standard cheesy pick-up lines and zero success with women in his earlier strips. His buddy Jase was much more realistic about the potential desirability of a couple of beer-guzzling couch potatoes.
  • In Rusty and Co., the halfling rogue Kris has a habit of ineptly, creepily, and repeatedly flirting with the women who cross his path, with no success whatsoever.
    "Play your cards right and one of these sandwiches could be yours..."
  • In a same-sex example, Shiro from Seiyuu CRUSH! is known to start conversations with cute guys with "yo, baby" (and a general overuse of "baby").
  • Duster from Slightly Damned. So far he's succeeded mostly at annoying his targets.
  • Sam "da Man" Sein from Sluggy Freelance.
  • In The Specialists, Henry brags that he has lots of chances, just no time.
  • Walkyverse:
    • Robin DeSanto is a female version (just for being so much of a No Social Skills Genki Girl), especially with the recent Reveal that she's a virgin. She is pretty attractive, though.
    • Smug Snake Faz owns this trope; he's both certain he's a lot more attractive and desirable than he in fact is (the permanent expression of self-satisfied smugness doesn't help) and is absolutely convinced that one day he and Amber will enjoin together in passion. He isn't going to let the fact that Amber openly and loudly detests him and everything about him dissuade him.
  • Weak Hero:
    • Bit Part Bad Guy Hayden is convinced that he's a ladies man who can get any woman that he wants. Like the rest of his boasting, it's all talk.
    • Wesley acts cocky when a hot girl is around, and his egotism makes him think he actually has a chance. His attitude is only seen as annoying, however, and contributes to his overall jerkassness.
  • White Dark Life:
    • Collin is an exaggeration of this. He believes he is attractive but his giant ego and weak physical stature quickly turn off any woman he has an interest in. And then it turns out his soul holds traces of pure chastity to boot, which guarantees this status.
    • Later, Kris takes this role from Collin once the latter cleans up his act. Only natural considering he's an incubus with pride as his main trait.
  • Alex from Wonderlab attempts to flirt with Rose on multiple occasions. However, their attempts tend to go ignored.
  • Zeus in Zeus' Godly Goodtime hits on pretty every good-looking lady in the whole series.
  • Taylor from Zoophobia.

    Web Original 
  • Suave, one of Bennett the Sage's alternate characters on Anime Abandon, complete with smoking jacket, a glass of scotch, and doing his best to channel Hugh Hefner although he usually just comes off as a sleazy git. He pops in every now and then to make jokes about the naughtier aspects of some of the anime featured on the show, and hosted it for the reviews of Golden Boy and Eiken.
  • ContraPoints examines the "pick up artist" type in one of her videos. It's pretty depressing, since the modern version doesn't seem to be about enjoying sex or liking women, but trying to prove something by entering a "conquest" into a spreadsheet.
  • Jake from Jake and Amir turns out to be this, as his quirks are established and developed later on. He talks a big game, and certainly seems to think a lot of himself, but is rarely successful with women.
  • Valentin from Noob regularly tries to pick up women with extremely cliched pick-up lines the second he meets them and continues trying when they show to not be interested. Laser-Guided Karma has hit him both in the webseries and novel version via the story being set in an MMORPG in which Cross Playing isn't unheard of.

    Western Animation 
  • Adventure Time: Lumpy Space Princess is a female example. She seems convinced that men find her irresistable and are always trying to "get on these lumps", but it's all in her head. Her attempts to seduce Finn and Jake in "Gotcha!" fall hilariously flat. And the one time a guy showed attraction to her, in "Bad Timing", Lumpy Space Princess ruined it with her own jealousy and bad temper (and also accidentally trapped him outside of space and time).
  • Danny Phantom gives us Tucker Foley. Tucker has tried to get a girlfriend several times over the course of the series with mixed results.
    Tucker: Hey there, I-
    Girl 1: No!
    Tucker: Hi, would you-
    Girl 2: Forget it.
    Girl 3: [Holds up hand.] No!
    Tucker: I didn't ask you yet!
  • Johnny Bravo: 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 as Word of God says Johnny does get lucky, it's just that his failures make for funnier TV.
  • It is implied that Homer Simpson from The Simpsons was like this before he met Marge, as evidenced by the time Lisa wanted advice on how to tell a guy (in this case, Ralph Wiggum) you aren't interested:
    Homer: Let me handle this Marge, I've heard them all. "I like you as a friend", "I think we should see other people", "I no speak English", "I'm married to the sea", "I don't want to kill you, but I will..."
    • Moe often attempts to woo not only Marge but every woman he sees (even Patty Bouvier, of all people) with little success.
  • Eddy from Ed, Edd n Eddy fits this trope superbly in several episodes, right down to the leisure suit and the gold medallion. Even though, Nazz doesn't have any interest in him whatsoever, much to his frustration.
  • Tobias from The Amazing World of Gumball is this. He even hits on girls who already have love interests (especially Penny, who is particularly unimpressed by his advances).
  • Family Guy:
    • Quagmire manages a good deal of success, but he's also failed enough times to not only develop an immunity to mace but also to be able to tell different types of mace apart.
    • Brian is also this, usually with more failures. Not only does he act like a tool just to impress women, but he's also known to date really stupid women so he can feel smarter than them and have an easier time getting in their pants, along with hitting on Lois several times. He has been called out on this as well.
  • Like Quagmire above, Boomhauer from King of the Hill is a partial example: he manages to have sex with lots of women, but one episode reveals that his method is to just hit on every woman he can find, usually with lame pickup lines, until he finds one that will give him the time of day. Bobby points this out to him, but Boomhauer's basic philosophy apparently is that one shouldn't let rejection get you down, though one episode had Boomhauer fall in love with a woman who only saw Boomhauer as a one-night stand and rejected his offer to marry her; man, he was dang ol' devastated, tell you what.
  • Martin Tubbs in W.I.T.C.H. - in the episode "H is for Hunted", he goes as far as to wear a leisure suit in an attempt to impress Irma.
  • Whenever Dr. Thaddeus S. "Rusty" Venture of The Venture Bros. 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, though he hasn't gotten laid in nineteen years — but he sure acts like it. Of his two known sexual encounters, neither was exactly healthy.
  • Carl from Aqua Teen Hunger Force. His schemes range from desperate to disturbed.
    • Shake is quite similar, to the extent that he vastly overestimates his own sex appeal. Oddly enough, Frylock has accidentally given himself away, a few times, as depressingly incompetent with women even when Shake and Meatwad aren't around to kill the moment.
  • Looney Tunes: Pepe Le Pew, with the joke being that his mates tend to be cats with stripes painted on them, some rather violent.
  • XR from Buzz Lightyear of Star Command. This is funnier because his voice actor is actually named Larry.
  • Daria: Charles "Upchuck" Ruttheimer III is Lawndale High's resident Casanova Wannabe.
  • Jonesy Garcia from 6teen.
  • Rover from Rover Dangerfield.
  • Jamie from Megas XLR. A lot of episodes have him fantasizing about picking up chicks but fails miserably every time. Even Goat the junk-yard owner has better luck than him.
  • Stroker from Stroker and Hoop.
  • Reef From Stōked. He probably won't even win Finn's love
  • Futurama: Zapp Brannigan. He sure acts like a stud but on first meeting Leela in "Love's Labours Lost in Space", she ends up having Pity Sex with him; This is later revealed to be his first, and for some time after, only sexual encounter. (The second was something he probably would have liked to forget...)
  • Butt-Head from Beavis And Butthead. "Hey, baby..."
  • Kenny from the Baby Blues animated series.
  • Total Drama:
    • Cody thinks he's a ladies man, mostly because his friends from outside the show are even geekier than he is.
    • To a lesser extent, Harold. He does win over Leshawna, but insisting Heather has a thing for him is too much.
    • Beth is a female example. As plain looking as she is, she claims to be irresistible to boys, hitting on Cody, Justin, and Harold over the course of two seasons and getting nowhere. Though she did win over a handsome guy named Brady, offscreen.
  • Ace McCloud of the Centurions.
  • Pam from Archer. Ultra-rare female example, although, unlike most male counterparts, she is equal opportunity.
  • Fruity from Downtown, much to the annoyance of his best friend Matt, who often has to prevent Fruity from getting both of them into trouble.
  • Kim Possible:
    • Motor Ed incessantly puts the moves on Shego, ignoring hints (up to and including plasma blasts) that she's not interested.
    • Zigzagged with Ron, whose attempts to woo women have gotten his rejected by nearly every girl he tries to hit on. However, this mostly stems from him trying to act like a traditional casanova instead of being himself, which has been shown to be more appealing as seen with severals girl who genuinely liked hm, especially his eventual girlfriend Kim.
  • Heath Burns from Monster High definitely qualifies.
    If you were a booger, I'd pick you first!
  • Odd from Code Lyoko. He claims to be a ladies man, but while he has dated most girls in his age group at Kadic, they all say otherwise. (In fact, the only girls that he can truly call friends are Yumi and Aelita, and neither is a girlfriend in any true sense.) Part of his problem might be the whole "dated two girls at once" thing that Yumi unfortunately took the fall for (due to being in his body at the time).
  • Mung Daal from Chowder who actually used to be The Casanova in his youth. Truffles tends to be a major factor in his failures, yet Chowder has sought him for advice on women a few times.
  • Brad from My Life as a Teenage Robot. While not a bad guy, almost every girl (except Jenny and one of the Space Bikers) he's met has simply turned their noses up at him.
  • In Gravity Falls episode "Roadside Attraction", Stan gives Dipper advice on how to talk to girls, claiming to be an expert on the subject. At the end of the episode, Stan's forced to admit that he's anything but. The end-credits cryptogram states that Stan's best relationship was with an animatronic.
    Stan: Alright, kid. I gotta admit something. I'm no expert on women. Truth is, I've been divorced once, and slapped more times than I can remember. Confidence can buy you a lot, but at the end of the day, pickup artists tend to get our heads bitten off. When it comes to women, I'm a failure.
  • Avatar: The Last Airbender gives us the Distaff Counterpart to this trope in the episode "The Beach". Behold, Princess Azula.
  • In the Justice League episode "Secret Origins", the Flash immediately puts his arm on Wonder Woman, much to her shock. He tends to flirt with most attractive women he meets, though in a subversion they often express interest, but only after he's already out of earshot.
    Flash: Dibs on the Amazon!
  • In Miraculous Ladybug, this is how Cat Noir tries to woo Ladybug. The irony is that as secret identity Adrien Agreste, he's legitimately popular with girls thanks to his modeling career and genuinely sweet personality, but due to his incredibly isolated upbringing, he thinks that over-the-top gestures and pet-names, like the kind from movies, are the best way to get a girlfriend.
  • The Mask: The Mask like Stanley does not get luck with any woman he comes across mostly because of him being too strong but however he makes up for it by being sweet, kind, polite, a Nice Guy and having charisma charm as well which brings most of them over to him.
  • Yakko and Wakko in the original version of Animaniacs. Hellooooooooo, nurse!

Alternative Title(s): The Leisure Suit Larry


Brock flirting

Brock attempts to flirt with multiple women and gets turned down

How well does it match the trope?

5 (27 votes)

Example of:

Main / CasanovaWannabe

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