The Brad in this Smirnoff Ice Triple Black commercial.
Anime and Manga
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. 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.
Bleach: Keigo loves women, especially if they have large breasts. He's never successful in his 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 (more Chivalrous Pervert) 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 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.
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.
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).
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).
Charlie Chaplin's Tramp character in Mabel's Strange Predicament, 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.
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 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 AuctionKings, 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.
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. Jay 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 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.
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 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.
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 Babysitter's 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.
Its 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 a gay man when he hits on a married woman by gossiping about her husband and wearing make-up and a girdle.
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 a MMORPG in which Cross Playing isn't unheared of.
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 KidAnova 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.
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.
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, and she was the victim in the first case of the series.
Another one used him as a scapegoat for a murder.
A third one left the country leaving a letter telling him to forget about her.
One time he didn't even manage to hit on the correct girl, instead he managed to creep out an old lady.
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, 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.
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.
Interestingly, the one time he does get a chance to have sex (with a woman who hasn't seen a man besides 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.
Another oddity (though he may be lying), he's actually good with girls (at least in regards to casual sex), as shown by a flashback in Expiration Date. Problem is, in his words, it's the ladies that he wants, and can't have.
Ringabel in Bravely Default hits on every woman he encounters and manages to annoy everyone around him in the process, including 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.
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.
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 Casinova.
Jaune flirts with most pretty girls he meets, particularly Weiss Schnee, who can't stand him. He mentions that he's just following his father's advice to show confidence and doesn't understand why it doesn't work. He genuinely does fall for her, however.
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.
James Ironwood has been friends with Ozpin and Glynda for a very long time and immediately flirts with Glynda when the trio meet. She dismisses him sarcastically and stalks out of the room. At the school dance, he asks her for a dance, but she rolls her eyes at him. Only when she spots Ozpin nodding his permission, does she agree. A short time later, Ironwood leaves the party early, seen off by Ozpin and with no Glynda in sight. Mercury and Emerald cattily comment that he's leaving because he's had enough fun for one night.
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.
Eridan Ampora from Homestuck 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.
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.
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.
Aaron West in Forever16, gets kind of sad knowing that a theoretical Time Skip would have him still be this.
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.
Collin of White Dark Life 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 interest in. And then it turns out his soul holds traces of pure chastity to boot.
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 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..."
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 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 - 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 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).