The juvenile serial dater. He hasn't even graduated from high school (possibly even middle school) yet, and he's already gone through as many girls as The Casanova, possibly more, high school dating being what it is. The only thing that differentiates him from The Casanova is that, because of his age and his show's target demographics, it's highly unlikely that he and his dates are having sex. At least, it'll be a cold day in hell before the Media Watchdogs let anybody even think about it.W
Compare Chick Magnet. His Distaff Counterpart is the Fille Fatale. If he's young enough, this may result in Toy Ships. NOT a child-friendly version of a statistical analysis technique.
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Anime & Manga
Shippo of InuYasha has won the hearts of many young girls, human and demon. Though some would argue that Shippou, being a demon and hence not subject to ordinary aging processes, is much older than he looks hence, only The Casanova of the regular variety.
This is relative, actually. He may be old in human years, but for all purposes he has the looks and the mentality of a young boy. He's still a child by youkai standards, just like Inuyasha is several decades old but is considered a teenager.
Actually, according to the Inuyasha Profiles, he's only 7 and is therefore a child by both human and youkai standards.
Negi of Mahou Sensei Negima! does this without even trying, or, indeed, even being aware of it. To paraphrase Chisame, it might be best to kill him before he hits puberty and starts noticing the attention he gathers with his every mannerism. He doesn't toss any of the girls away, of course, since he doesn't even realize he's seduced them (and most realize he doesn't, and thus don't end up too heartbroken) – and at least one is more open to the "harem" scenario than she'd like to admit.
He actually has a Heroic BSOD every time someone pulls him aside and tells him he's accidentally seduced several (more) of his students (this has happened at least twice). The very next thing he does accidentally seduces the girl who had told him that.
Chisame: Here he comes! His natural gigolo talk! (Again?!) Chamo: That's my aniki!
As per Pokémon's Ash Ketchum's inability to age, he has been shown to have garnered a rather respectable number of young women's affections at the canon age of ten (which has been pushed for the past two decades). However, he's still dense as a rock. As of the most recent series, this canonical list includes Misty, Melody, Macey, Bianca/Latias, Anabel,Angie and now Serena is starting it..
Gary Oak. He has his own cheerleadering squad, and Dawn was a fangirl of his.
Durarara!!'s Masaomi Kida, whose surname even begs for a punnerific joke involving this trope, hits on girls left, right, and center, though it's later revealed this behavior is almost entirely a front. His heart belongs to one girl and one girl alone.
Momochi from Level E. When it's revealed that the password to unlock the bracelets is the name of the girl they like, most of the kids say a name or just "nobody in particular." Momochi lists off the names of about twenty different girls, only to be told that his answer is invalid because he left some out. He lists off five more, and is told that there's still one left... Who turns out to be a girl he met in passing, and thus doesn't know her name. Then there's the time they helped out the twin-tailed mermaid. At the end of the episode, most of the kids offer their condolences. Momochi offers his phone number.
Mizuiro from Bleach is known to be able to get women much older than him fawning over him with pretty much the snap of a finger. How many guys can you name that while in their teen years, can go with their girlfriend, who is an older woman, and nine of her friends, to Hawaii for the entire Summer vacation? James Bond, eat your heart out.
Although the story that shows his point of view right before the series itself starts has him waking up one of those women's room, so he may just be a regular, younger-than-normal Casanova.
In Tenchi Muyo!, Tenchi has several adult women flirting with him, including two who seriously want his love (who is how serious about having him, though, is one of many things that changes from version to version.) One is even a distant relative of his (that's just how Juraians roll, as she explained.) He's seventeen. Of course, that's just going on the ages they look. A lot of the cast can measure their ages in three or four digits - which actually may explain it. What's 15 vs 18 mean to you when your kid sister is the Trope Namer for Really 700 Years Old? Tenchi Muyo GXP is the same with its protagonist, Seina, who appears even younger than Tenchi.
A young Romano in Axis Powers Hetalia is only willing to learn enough Spanish to demand kisses from Belgium and the Queen of Spain. Once Belgium takes him up on it, however, he finds himself at a total loss.
DJ (Mark Sheppard) of the New X-Men, voted "class flirt" by his friends. Even as he lays dying after being blown up by the Purifiers he still takes the time to hit on the newly-arrived X-23 before succumbing to his wounds.
TheGreatAlicornHunt: Arguably, Breezy Shy, Fluttershy's kid brother... who within moments of his first appearance has all four members of the Cutie Mark Crusaders glomping onto him.
The 1995 Larry Clark film Kids is about a 17-year-old Casanova who specializes in virgins. After his last conquest (13-years-old) discovers she's HIV-positive, she decides he has to be stopped before he passes the gift that keeps on giving on to another girl.
In Don Juan DeMarco, the titular character claims to have discovered his vocation very early in life. He committed his first act of peeping-tomfoolery before he was old enough to walk.
Rant, a.k.a. Buster Casey. Racked up a list of most of the females in his school before he left home. Notice the use of the word "females", not just the female students.
Otto in Someone Else's War is very kind and polite, but always the first to appreciate a girl's beauty, quite vocally at that. (He's twelve.)
In The Gerosha Chronicles, older Donte is generally ignored by women - except for his clingy girlfriend Candi. Donte, from the time he meets Candi, seems to have eyes only for her. But when Donte was much younger and long before he met Candi, such as in the timeline of the story Of Emeralds and Sapphires, young Donte seemed to have an Unwanted Harem. Nearly every girl in the neighborhood had a crush on him, though girls were invisible to him at the time. He was far too busyavenging Hector and trying to be a Morality Chain for the Sapphire King.
Sunny's brother Chukwu in Akata Witch, to the point that Sunny wrote an essay about it. He struck out hard with Sunny's friend Chichi, though.
Swedish writers Anders Jacobsson and Sören Olsson usually have main characters, who are what they like to call "girl charmers". Sune is between seven and eleven years old, Bert is between eleven and sixteen years old.
Live Action TV
Drake of Drake & Josh. Very much so. An official count numbers the girls he's shown dating in the series to be over 60. You will never see him dating a girl you saw him date in a previous episode. Add that to the fact that he is shown dating a girl nearly every episode and you have yourself a lot of dumped girls.
In one episode, we see him with three girls: a girlfriend from a previous episode, his current girlfriend that was introduced in another episode, and a previously unknown girlfriend.
Subverted in How I Met Your Mother with Matthew Panning, "the Stud of Port Richland Middle School", who claimed to have had sex with a hundred girls by the time he was 12. It's obvious to everyone that he's lying, except for Barney, who makes it the goal of his adult life to sleep with 200 girls just to show Panning up.
Every single live-action show on Disney Channel seems to have at least one.
During season 2 of Degrassi, when JT who's 13 at the time instantly starts making plans on dating the most popular older high school girls he can catch.
The title character in Big Nate intensely wants to be this. A lot of the strip follows him as he flirts with the prettiest girls at his school and gets shot down.
Older Than Radio: Mozart's opera The Marriage of Figaro has a boy, Cherubino, who is old enough to get shipped off to the army but young enough to be a Cross Dressing Voice role, and spends the show charming every woman he can get his hands on. He ends up in a Beta Couple (with Barbarina, the local ingenue) by the end of the night. Lampshaded by his song "Voi chi sapete", in which he explains that he loves being in love with all the ladies around and it's a natural thing to him. And, in the original plays by Beaumarchais it goes further: the sequel The Guilty Mother says he's the father of Countess Rosina's child.
Stacy's Mom by Fountains Of Wayne is sung from the point of view of a kid who believes himself to be this.
Bluebottle from The Goon Show wants to be this, and often declares that he will use his Comically Small Bribe to seduce various girls, but his sexual fantasies always end without any sex happening (except in one case where the woman he's fantasising about is implied to end up with Eccles inside his fantasy), so it isn't actually clear whether he actually has any success with the girls. With No Continuity, it is probably easiest to say that the answer varies.
Shantotto's hardly his only victim. He hits on everyone from Tifa "Boobs of Steel" Lockhart, who's in the 20-23 range, to Cosmos, the Goddess of Harmony. Then there's his choice to tackle Garland over a gap that few of the characters can cross without aerial evasion abuse note to elaborate: Garland's sword dwarfs Cloud Strife and his Buster Sword, Garland is bigger than his sword, and he is covered head to foot in armour bar one of his alt costumes because he 'didn't feel like fighting a lady' - referring to Ultimecia, the time witch.
Nils Lutefisk from Psychonauts is one of these. He claims it's because his parents let him watch R-rated movies.
Roy from Fire Emblem 6 is just fifteen years old, but he can have up to six possible love interests: his gorgeous ex-teacher, his childhood friend, a cheery Lethal Chef, a silent female nomad, a cute mercenary girl and a shy half-human, half-dragon shaman girl.
From Fire Emblem 8, we have Ewan. This redheaded, cheery magic student can't be older than 15, but he can date and eventually marry Amelia, a sweet girl who's at least two or three years older than he is.
More importantly, in his support conversation with Ross he claims to have "a lot" of girlfriends, though we have to take his word on it.
15-year-old Erk the Mage has three possible girlfriends (Serra, Priscilla and Nino). Though, he is very anti-social and even laments his inability to talk to girls at one point.
Dew from Fire Emblem 4 may have them all beat: he can marry and have kids with most of the women in the player's army (and not in the future tense, either). His exact age is unclear, but definitely early-to-mid teens. (A manga adaption gave his age as 14!) And several of the girls are older than he is! (15-year-old Raquesis and 14-year-old Sylvia are around his age, but Briggid and Adean are at least in their mid-to-late teens.)
Poo from Earthbound is implied to be this. He has fangirls in his hometown, anyway.
Persona 4 gives us Teddie, who may call his continuous date-hunting "trying to score", dialog however makes it rather clear that he has no idea what the term actually means. Add to that the fact that his true age (depending on where you start counting) is possibly less than one year, and you get this trope in spades.
Alex of World of Fizz is definitely a prepubescent pervert, though none of his crushes (a classmate, his sister's girlfriend, the school nurse...) have shown much interest in him.
Jake English of MS Paint Adventures is desired romantically by all three of the other main characters from his universe. At least part of this is that he is (as far as they know) the only viable option (it's certainly not because he's so suave).
The web novel Seeking a Sweet Bewitching Kiss as part of the Girls Love series Sono Hanabira Ni Kuchizuke Wo contains a female and lesbian version of this trope. Elementary schoolgirl lesbian Runa, has all the girls in her class as well as her teacher (a woman in her early twenties) enamored with her. Recently, she has gotten her own visual novel released, in which she kind of subverts the trope by having sex with her teacher.
Among Zorian's classmates in Mother of Learning is Benisek, a boy whose primary occupation at school is the pursuit of girls.
Odd Della Robbia of Code Lyoko. He even managed to get somewhere with his friends' love interests, if only at a stretch (a platonic dance date and a Fake-Out Make-Out for Yumi and Aelita, respectively). The only girl he hasn't (willingly!) dated is the Alpha Bitch, and even then there's enough UST between them to rival Ulrich and Yumi.
Amusingly, it comes back to bite him later when his reputation has gotten around and he suddenly can't get a date to save his life.
Part of the problem is that his feet stink. One girl had to continuously douse herself in perfume to just SURVIVE the date.
And don't forget Jeremie's attempt at making a Polymorphic Clone of himself. That clone was Odd-like in terms of romance.
Ferb doesn't have nearly as much success as Butt Monkey, Baljeet. So far, he has gone on a romantic cruise with his childhood friend Mishti, actually kissed a female friend named Wendy (who seemed to like it), and managed to unwittingly become the crush of Fireside Girl Ginger.
Jonesy in 6teen is one of these, but he fails to get the girls just as much as he fails to get a stable job.
He got Nikki, didn't he?
James Bond Jr. seems to have learned more than just fighting skills from his uncle.