Casanova Wannabe



""Is heaven missing an angel? 'Cause you got nice cans!""

- Dating Robot #1, Futurama

He wants to be 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.

Anime and Manga
""I need someone who's mechanically minded, not some half-baked, swashbuckling Casanova wannabe!""
 * Bernard Monsha in Gundam 0083 IS this trope incarnate.
 * 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:


 * 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 for a fiancée.
 * Iwata from Excel Saga.
 * Sena in Cross Game
 * To some degree, Captain Kyouraku Shunsui from Bleach.
 * 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.
 * Taniguchi, one of Those Two Guys in Suzumiya Haruhi.
 * Axis Powers Hetalia: Francis Bonnefoy (aka France) is somewhere between this and the Casanova. None of the other countries find him very appealing, but it's implied that he has lovers, and he does manage to successfully molest (or at least strip) several of the other male countries (and at least one female)

Also seen in regards to Feliciano Vargas aka North Italy, much to the despair of his partner Ludwig aka Germany.
 * One Piece: Sanji never has and most likely never will score with any of the chicks 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.
 * 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.
 * 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
 * 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.

Comic Books

 * 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).
 * From Superman: WGBS and Daily Planet sports reporter Steve Lombard, especially in All Star Superman.
 * One of Rudi's buddies is the most obnoxious one you can think of. Sometimes however he is successful.

Film
""Please, call me what everyone else calls me: 'Your Royal Sex Machine.'""
 * "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.
 * Jay from The View Askewniverse
 * Ron Burgundy of Anchorman: The Legend of 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.
 * Dawn of the Dead 2004 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.
 * Brain Donors: Roland T. Flakfizer talks a great game.


 * Salty from Alpha and Omega is basically a wolf version of this trope.
 * Harold "Hutch" Hutchison from Fan Boys.
 * 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.

Literature

 * 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 Wraith.

Live Action TV
"The Todd: Whoa, these are hot. [referring to two pieces of broccoli]
 * Jay on Herman's Head, but Jay is also Looking for Love In All The Wrong Places.
 * Larry Dallas of Threes 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%.
 * 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:

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: Hey, Lisa. I heard you lied and said we didn't do it. Admit it. We doinked.
 * 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.

Lisa: I was sad because my dad died.

Todd: I wasn't."


 * Col in The Adventures of Lano and Woodley.
 * 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.
 * Julian Bashir of Star Trek Deep Space Nine.
 * To be fair, Julian does sleep with Ezri Dax at the end of the series. After 7 years of trying to get together with Jadzia Dax.
 * 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.
 * Well, this is Bruce Campbell we're talking about here. "Hail to the king, baby!"
 * 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.
 * Are you kidding? He's so far out, even his grandmother is setting him up with guys! (as he himself put it.)
 * Buffy the Vampire Slayer 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: Nicol Ã¡s 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 Nicol Ã¡s, 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 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, It Gets Worse. 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.
 * 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 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.
 * Manny from Modern Family is a Kidanova wannabe.
 * 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 Vampire and 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.)

Music

 * The Creep by the Lonely Island has several.
 * Sonic Youth's "Swimsuit Issue" is about a guy from Geffen Records who annoyed the band by acting like this.

Newspaper Comics

 * Jon from Garfield, although he finally had success with Liz, after 28 years.
 * 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.
 * 'Spit' Murphy from Footrot Flats.

Professional Wrestling

 * 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.

Theatre

 * 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

 * Of course, the eponymous Leisure Suit Larry, the former Trope Namer.
 * 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.
 * Raidou Kuzunoha VS King Abaddon: Of all people, Rasputin.
 * To be fair, some of the ladies in the red light district seem to be quite impressed with his, er, talents. It's just that this doesn't get him anywhere with the women whose affections are not for sale.
 * 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.
 * Baldur's Gate II:
 * 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.
 * 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.
 * 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.
 * His idea of being smooth and seductive: "Are you sure you're not a baker? 'Cause you've got a nice set of buns!"
 * Ewan Devlin from Mercenaries2: 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.

Web Animation

 * 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!"
 * To be fair, his universe seems to run on The Smurfette Principle, seeing as Marzipan is the only woman we ever see. Though he did have that brief hook-up with The Ugly One through the use of Author Avatar...

Webcomics

 * Slick of Sinfest.
 * Robin DeSanto of the Walkyverse may qualify as 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 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 ?
 * In Misfile this trope is filled by Colin the Counter Guy in the local autoparts store.
 * Sam "da Man" Sein from Sluggy Freelance.
 * El Goonish Shive got one such guy -- T.C., aka "The Playah", a student of Moperville North who works as a clerk at the movie theatre. Being an Acceptable Target, he also works as a Butt Monkey out of the main continuity.
 * 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.
 * Duster from Slightly Damned. So far he's succeeded mostly at annoying his targets.
 * From Little Gamers, "Did it hurt when you fell from heaven? Because your face is really fucked up."
 * In The Specialists, Henry brags that he has lots of chances, just no time.
 * 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 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.
 * In Ears for Elves, Elon tries to follow Rolan's smooth style of talking to the elven women. They are not impressed.

Western Animation
"If you were a booger, I'd pick you first!"
 * Johnny Bravo, anyone?
 * Disco Bear from Happy Tree Friends. Obviously the best example on the show.
 * Eddy from Ed Edd and 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.
 * Martin Tubbs in WITCH - 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. Ironically, Rusty's not a virgin.
 * Though he hasn't gotten laid in nineteen years.
 * 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 Cananova Wannabe.
 * Jonesy Garcia from Sixteen.
 * Rover from Rover Dangerfield.
 * Jamie from Megas XLR. A lot of episodes have him fantisizing 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 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.
 * Butt-Head from Beavis and Butthead. "Hey baby..."
 * Kenny from the Baby Blues animated series.
 * Total Drama Island: Cody and to a lesser extent, Harold.
 * 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.
 * Motor Ed in Kim Possible incessantly puts the moves on Shego, ignoring hints (up to and including plasma blasts) that she's not interested.
 * Heath Burns from Monster High definitely qualifies.