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 maybe he's a klutz or uncomfortable, despite his dedication to pursuing the ladies. 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 he's the original ladies' man and that his bed is never cold. But the truth is, he's still a virgin (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). Every woman in a ten-mile radius can see the blinking neon "loser" sign bolted to his receding hairline. 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.
Generally he's bound to succeed once or twice, by law of averages if nothing else. These relationships usually don't last long.
See also Looking for Love in All the Wrong Places — the two character types complement each other and sometimes overlap. Also Handsome Lech, who is this same character with the plus of being attractive (but still with no luck, and even less of a clue).
Compare Nerds Are Virgins and Extraverted Nerd. Contrast Kavorka Man, Even the Guys Want Him. For a female version, see Abhorrent Admirer.
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Anime and Manga
Cross Marian of D. Gray-Man: He likes women, and flirts like there's no tomorrow. However, he's not exactly a good person, so good/classy women usually don't like him. Most of his sex and sexual experiences seem to come from hookers. His official character info states he flutters around and gets burned a lot. And, one of his hobbies includes visiting the Red-light districts. Only in anime filler episode 27, did it paint Cross as being a complete 100% Casanova
Cross flirts with Klaud 9, a fellow general who used to be an animal trainer. She's very reserved, and dignified, but she finds Cross hopeless, and seems to be completely uninterested in Cross.
He flirts with the main heroine, Lenalee. However, when he compliments her on her beauty, she changes the subject. He then cups her face, saying had he known she was around, he'd have been there sooner. She tells him flattery will get him nowhere with her.
We only see one lover of his in the manga, Anita. She was a prostitute. She was a kind and caring women. She was crazy about Cross, saying she'd do anything for him if she can help. She also cries after thinking he's dead, and when she finds out he may be alive, hops on a ship to go search for him. Her strong devotion to this man, makes it seem Cross may not be so bad. However, Anita, being a hooker probably has had run-ins with lots of horrible men. Cross, she has known a while, being 27 and having met him as a teenager, is probably just one of the best men she's had, which doesn't say much.
He was also a lover to Anita's mother, who was also a prostitute.
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!"
Ataru 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. Or maybe he'll just grope her. This despite having a hot alien babe (who has electric powers and is deathly jealous, to boot - just do the math) for a fiancée.
Bleach: Keigo and Kon love women, especially if they have large breasts. They are never successful in their attempts to attract a single one.
Kazuharu Fukuyama in Girls Bravo is possibly an even better example than Leisure Suit Larry. He has a habit of feeling up women whenever he so much as talks to them, and he has the resources to have a mansion with such features as central air in the flooring to blow up skirts, and an elevator that takes women's measurements.
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.
Brock and Ash's Oshawott from Pokémon. (Fortunately for Brock, he usually has someone, usually Misty or his Croagunk, to pull him away from a girl he hits on before he makes a complete fool of himself.)
Masomi Kida from Durarara!!. His attempts at wooing women fail to the point where even his partnerMikado lampshades his failures. However he stops when he gets back with his former girlfriend, Saki Miyajima.
Sunohara from Clannad has some elements 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.
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.
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.
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).
"Snake Hips" from Shaun of the Dead - while we never see him "in action," it's implied he's like this due to his... interesting outfit and the backstory Ed supplies for him. He eventually gets lucky with a horde of girls. Unfortunately he doesn't live long enough to appreciate it.
Moe from Slap Shot. 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.
Demian: Emil Sinclair from Hermann Hesse's novel arguably fits this, as he talks the talk, but actually the only move he made was a crush on a store keeper. That happened during his school days. Later, he did have a brief romance...to his best friend Max Demian's Hot Shounen 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.
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.
Marco from Animorphs is a particularly young version of this.
Live Action TV
In Smallville, Bart, who hit on Chloe twice, with the second time failing especially spectacularly.
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.
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 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.
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.
He has had notable success, perhaps too much to be considered the Cananova 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.
Subverted on Burn Notice - even though Sam acts, dresses and looks like an archetypal Cananova 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. In the awful movie, A Night at the Roxbury, they were named Doug and Steve Butabi. Other examples of a Cananova Wannabe on Saturday Night Live include:
Christopher Walken's "The Continental"
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])
Subverted with Larry (hmm, Shout Out?) from Buffy the Vampire Slayer, who displays this behavior for a while, only to have it revealed 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 toyed with the idea in "Teacher's Pet"; one of the victims was very embarrassed when told that the mantis only attacked virgins.
Yo Soy Betty La Fea provides us with two: NicolĂˇs 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 best dressed) than NicolĂˇs, 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.
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 Cananova Wannabe.
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 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 Cananova 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 Babysitters A Vampireand HOW. Every episode has multiple examples of their romantic failure. (Though in his defense Ethan is no where near as bad as Benny, and Benny in turn isn't as bad as Rory.)
Bobby Lee’s character Tank, from Mad TV, is a clear example. Despite his many elaborate attempts to score with women, he remains a virgin.
Paramedic John Gage on Emergency! gets teased for being this by Fireman Chet Kelly who doesn't seem to do any better with women.
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.
Dean the pig from Liberty Meadows, where all the animals are anthropopathic, if not anthropomorphic.
Fillmore from Sherman's Lagoon goes to mating season every year at Ascension Island and consistently fails horribly.
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.
Nate Wright, the titular character from Big Nate is a Kid Anova Wannabe. His combination of utter cluelessness and unwaning self-confidence when it comes to girls is a central theme in the comic.
A common character type in pro wrestling; WWE's Zack Ryder is the most visible example at the moment. A gullible, self-absorbed, outspoken loser, Ryder will often pick up and lose a Diva escort over the course of a show.
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.
Phoenix Wright: Ace Attorney: Larry Butz, of who has hit on, essentially, every girl he sees and who has been rejected probably hundreds of times. Larry has succeeded a few times, too. Admittedly, those times seem to have a tendency to end badly. The one girl who actually genuinely had a crush on him was killed by the very clock Larry made for her.
Super Robot Wars Advance: Axel Almer, when picked as the protagonist, becomes some sort of this, flirting with every girl he sees and failing horribly in each attempt. For example, when he is asked for his name by Sayaka Yumi, his answer was: "Maybe I'll remember my name if a beautiful girl like you kisses me". This added more reasons why he's called Ahoseru.
Not to mention a 4koma re-enacting this scene (when Axel and Sayaka are in their respective mechs) has a Rocket Punch belting Axel's mech immediately from nowhere. Hilarity Ensues, indeed.
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.
An elf called Salvanas found a bar — a minor character whose only function is to try to hit on every female character that talks to him (though they apparently forgot to give him any dialogue for Imoen) so blatantly shamelessly he's inevitably rejected angrily. If a female player character chooses NOT to reject him, he gets scared and runs away.
Imoen was pretty much added in at the last minute as a party member
Also, Edwin (After a hilarious accident). He hits on Mazzy.
Jak and Daxter: Daxter is like this. He flirts with every attractive female in the series, 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.
Edgar of Final Fantasy VI is one, so very much. It seems to be played mostly for incongruous humor, though, as women shoot him down in spite of his wealth, power, looks, intelligence and sense of honor when any one of those qualities could easily attract someone, if not every girl he meets.
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.
Rock from 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.
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 ... and also dumped him. In truth, there is some hint that Oghren's lecherous behaviour is a cover for his crippling insecurities.
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.
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 to exasperation. Thoma got game, his teacher just programmed him not to use it consistently.
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!
Despite his claims of prowess with the "lady-types", Strong Bad from Homestar Runner is definitely a Cananova 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!"
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 sister (or so he claims) and an alien. The latter, it should be noted, was non-consensual. For Tucker.
Robin DeSanto of the Walkyverse may qualify as a female version (just for being so much of a No Social SkillsGenki Girl), especially with the recent Reveal that she's a virgin. She is pretty attractive, though.
Smug Snake Faz owns this trope in the Walkyverse; 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.
What about the fact that they are probably related?
In Misfile this trope is filled by Colin the Counter Guy in the local autoparts store.
Eastwood in Exterminatus Now, 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.
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 you creepy loser" way and not the "I love to hate you" way.
Eddy from Ed Edd N Eddy fits this trope superbly in several episodes, right down to the leisure suit and the gold medallion.
Ditto for Quagmire from Family Guy, who 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 he acts like a tool just to impress women, he's also known to date really stupid women so he can feel smarter than them and have an easier time to get 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 pick-up 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 Brothers 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.
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.
Reef From Stoked. 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...)
Odd from Code Lyoko. He claims to be a ladies man, but while he as 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.)