A trope common in Romantic Comedies and Teen Comedies, in which a dorky (not necessarilyugly, just... geeky) guy ends up with the totally hot babe. Generally, the geek begins the story as an outcast whom the beautiful girl would never be attracted to. He may be a band geek, or a scientist with all the social graces of a tube worm, or a D&D player who still lives in his mom's basement. And through the course of the story, she begins to see through his spaz-like exterior to the decent, love-worthy man within.
Often, the guy will be smitten with the girl the first time he sees her. She, on the other hand, won't be attracted at first, and will often fight the attraction later on in the story. Eventually, despite whatever Three's Company-style misunderstanding crops up (and it will; you can count on it) she comes to realize that there is more to the geek than his pocket protector and love will bloom. It is neverLove at First Sight for the babe, in any case.
Related to Ugly Guy, Hot Wife, and subject to the same Double Standard, since gender inversions are practically non-existent; there may be more to the male geek than his pocket protector, but for women, looks are all that should matter. If a Hollywood Homely geek girl (or Hollywood Homely non-geek girl, for that matter) sets her sights on a hot guy, she might be able to make afew slightalterations, but it's more likely she'll just be the Abhorrent Admirer who makes him run away in terror.
Also extremely rare is the male geek that actually considers a similarly geeky girl, due to the latter's rarity in media in general. This holds even for works aimed at a female audience, and therefore any nerdy girl will eventually be revealed to be Beautiful All Along.
Compare Savvy Guy, Energetic Girl and Nerd Nanny. See Nerds Are Sexy, Adorkable and Geeky Turn-On for when the attraction isn't despite nerdiness, but because of it. Contrasts with All Girls Want Bad Boys. Often overlaps with Just Friends.
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A Go Daddy Super Bowl ad once had a smoking hot model making out with a nerd (who turns out to also play one of the background geeks from The Big Bang Theory.) The reaction to it was pretty much universally negative, mainly because of the apparently intentionally disturbing close-ups and sound mixing.
What the Wife did in Spotted Flower and likes to make the Husband remember that so he can be more confident in himself, despite being a hardore oraku, he got a girlfriend, had sex with her, they married, and now she's is expecting their child.
Paprika: Chiba admits to Tokita she loves him and towards the end, Konakawa is informed that they are getting married.
Gender-Flipped in Vandread, where geeky mechanic Parfait is paired with Bishōnen doctor Duelo. The idea is that since both sexes are re-learning about each other, the normal social divide that would say he's out of her league doesn't exist.
By all accounts Peter Parker is an average-looking guy who is incredibly nerdy, he still managed to date three bombshells before marrying a supermodel.
This hasn't gone uncommented — Pete's friend Johnny Storm (otherwise known as The Human Torch) has pointed out the sheer number of gorgeous women that Spidey has dated, including Gwen Stacy, Mary Jane Watson, and the Black Cat (although Black Cat is more about Spidey than Peter).
He's also recently caught the attention of Ms. Marvel.
His cause is helped by the fact that most artists post-Steve Ditko have given him a significant amount of male polish.
Also lampshaded in the Ultimate Universe. When Johnny Storm tells Peter that he met a hot girl from the world of Spider-Man, Peter starts listing off every super powered female he'd ever run into. Much to the annoyance of Gwen Stacy and the envy of Johnny, Bobby, and (again) Gwen Stacy.
Amadeus Cho, the 7th smartest person on Earth (as verified by a soap company - oh, and Reed Richards). Managed to win the heart of a Perky Goth Amazon Gorgon girl. It must be noted that the looks are inverted, as the aforementioned Amazon Gorgon got her looks from Medusa, while Cho is always drawn quite handsomely.
Runaways provides a rare Gender Flip: short, chubby, average-looking nerd Gert ends up with tall, blond athlete Chase.
Film — Animated
Milo and Kida from Atlantis: The Lost Empire. Milo fits perfectly the nerd description being lean, with glasses and a bookworm; Kida even lampshade it when they met:
Kida: You are a scholar, are you not? Judging from your diminished physique and large forehead, you can be suited for nothing else!
Kida herself is a princess in a stripperiffic outfit, (for the standards of the era) but she soon learn to appreciate Milo. She always had interest in him though, because he can read her forgotten language.
Played straight with Hiccup in How to Train Your Dragon. He's smitten with Astrid first thing, but she hates him until she finds out his mindblowingly cool secret and, more importantly, how brave and principled a warrior he actually is. Unlike most examples of this trope, however, Hiccup is far from bad looking.
Doctor Doppler and Captain Amelia in Treasure Planet. He's a bespectacled doctor in astronomy and not quite fitted for adventure. Thus the Captain and him develop a Belligerent Sexual Tension until they're kidnapped together and begin to warm up.
The Ship Tease of Po and Tigress in Kung Fu Panda: the roly-poly overenthusiastic Ascended Fanboy and the Amazonian BeautyactionCat Girl. He may be geeky, but he proves in both films that he can succeed where she fails. In the first film, it's by being his own wacky, clumsy self. In the second, he masters a highly-advanced technique in a matter of days or weeks, a feat that took Master Shifu many years.
Louis: 'cause all jocks think about is sports. All we ever think about is sex.
Nick and Norah's Infinite Playlist: The geeky, unmacho Nick gets the girl, naturally. (Inverted in the book, where she is somewhat dowdy while he is compared to a gay porn star.)
In the American Pie films, Jim Levenstein and Michelle Flaherty fit this trope. While it's true that Michelle is also a geek (specifically, a band geek), she's a sexed-out band geek played by Alyson Hannigan. Partially subverted in-universe though- Jim initially dismissed Michelle for her dorkiness, whereas she seems to have chosen him at least partly by physical attraction.
Weird Science: Gary and Wyatt get the girls with the help of Lisa, their artificial woman.
In his movies, Woody Allen has dated or been married to Téa Leoni, Goldie Hawn, Helena Bonham-Carter, Elizabeth Shue, Julia Roberts and Mira Sorvino, among others. Of course, given his string of real-life wives, this could also be a case of fiction imitating reality.
The 2008 Get Smart movie has Maxwell Smart (played by professional nerd Steve Carell) and gorgeous bombshell Agent 99 (played by authentic hotness Anne Hathaway) hook up.
2009's I Love You Beth Cooper. High school valedictorian stalker nerd with enormous nose meets up with Hayden Panettiere as Beth Cooper. Nuff said! They don't actually end up a couple at the end, although he plans to continue pursuing her after the film. She does mention that she envies him. He might be a nerd, but he's going places, while she's a popular girl who may go to a community college.
Sideways. Lampshaded by Paul Giamatti's long monologue comparing different types of wines.
Subverted in A Cinderella Story in that by the end, the Alpha Bitch is willing to give the geek a chance - but he chooses the weird, purple-haired announcer girl. Not to mention the real reason why she wanted to get with him was after he starred in that commercial and became popular. Earlier, after they had kissed during the ball and when she found out she had actually kissed him, she promptly expressed her disgust.
High School Musical offers a gender-flipped version, with basketball star Troy falling for shy, science geek Gabriella. Gabriella is very attractive, but the fact she's on the academic decathalon team, gets labelled the 'freaky math girl', and her Establishing Character Moment is reading a book at a party, plants her firmly in geek territory. However they're both equally smitten from the moment they meet, and Troy is outright proud of her achievements rather than put off.
Hilariously subverted in National Lampoon's Stoned Age, when the nerd is, and is called a complete moron by everyone, watches his dream girl marry his jock older brother, and when the girl is kidnapped by a rival tribe and his own tribe runs away, the nerd goes through the trouble of trying to rescue his beloved, only to find out that she's staying with the rival chief, because he's manlier than her brother, and provided her with furs, jewelry and food. Also, he has guaranteed sex with a tribe of hot amazons, but naturally, he fucks it up. In the end though, the nerd doesn't die a virgin, because he had sex with a monkey,
Applied with irony when geeky accountant Louis Tully keeps hitting on pretty cellist Dana Barrett, despite Dana's constant hints that she wants absolutely nothing to do with him. However, once they're both possessed, they merge the key and the gate. In the sequel Louis and the Ghostbusters' Sassy Secretary Janine Melnitz end up babysitting Oscar and, after some wine and pizza, start making out on the couch.
Janine also experienced Ship Tease with Egon, The Brain of the Ghostbusters, both in the original film and in the animated series. Egon's first reaction with Janine is to come out from under her desk, in a possibly suggestive manner (he was fixing her computer), she cries into his chest when she worries he might die in the showdown with Gozer (he reciprocates with an awkward hug), and comes up to Egon eagerly once they've defeated him. In the cartoon, he's Oblivious to Love, to the point where she lets an evil fairy possess her and change her appearance, hoping she'll finally get Egon's attention. The Janine/Louis relationship is part of why some fans (especially those who grew up with the cartoon) disavow the second film.
In Back to the Future, sci-fi writing and socially inept George McFly gets the girl, though with a bit of help from his time traveling son. Although, he still managed to get together with Lorraine originally even without the help of his future son. The difference being, due to Marty's involvement, was how they got together, ultimately ending up improving their lives drastically, which Marty discovered upon returning to 1985.
Subverted in Wet Hot American Summer with Katie and Coop. Though she seems to warm up to him and even confesses her love for him, at the very end of the movie she rejects him for the hot Jerk Ass Andy, telling Coop that she really likes him, but she just wants to have sex with a hot guy and she doesn't care if he treats her like crap.
Neurotic, geeky Columbus and hot "bad girl"-type Wichita in Zombieland are a pretty textbook example, although it probably helps that he may be the only guy her age left after the zombie apocalypse.
In The New Guy the geeky and socially awkward Dizzy ends up with head cheerleader Danielle.
She's Out of My League has this as central plot driver. In fact, the geek is constantly trying to find some kind of flaw in the girl in order to justify to himself and his friends why she's with him. When he finds one (her toes are slightly out of proportion), he's disappointed, and they end up breaking up over this. They do get back together at the end, though.
In 10 Things I Hate About You, the beautiful and popular (for her age, at least) Bianca eventually chooses the fairly-geeky Cameron over the super-popular Joey when she realizes he's a legitimately nice guy. Kind of subverted, as Cameron really isn't that geeky at all, he just has to put up with the social stigma of being the "new guy." Part of the story involves Bianca finding out that many of her preconceived notions about people are wrong.
The Sorcerer's Apprentice has a science nerd get together with an attractive art student. Oh, and he's also a sorcerer. Oddly enough, the latter actually interferes with his attempts to get her to like him. Plus, she probably remembers that he actually used to be a cool kid in school until "the incident".
Scream 4 has an unusual zig-zagged version. Hot Tomboy Kirby has a thing for Nerdy Charlie, but can't close the deal due to a Moment Killer. Turns out, Charlie's had the hots for her for awhile but that doesn't prevent him from trying to kill her later, which may have been fueled by Kirby's Oblivious to Love attitude towards him for the last several years.
In X-Men: First Class, Raven is incredibly forward with Hank. Unfortunately, he's too caught up in angsting over being a mutant.
It is stated that Jones, the sonar technician of the USS Dallas, because of his nerdy looks and knowledge, gets enough action on the beach to "wear down a squad of marines".
Oliver Tyler, a former nuclear submarine officer (retired after losing most of his left leg) and computer nerd, though also a former American football player, has "five and two-thirds" children with his wife, "making up" for lost time while a submariner.
The latter bit about a male geek never pursuing a female geek is subverted in the later book, The Cardinal of the Kremlin. Major Gregory, a huge geek and the head of the book's US SDI program is in a relationship with another, female geek, who specializes in mirrors, which Major Gregory uses in his laser defense system. A match made in Heaven. If the universe, a certain jealous lesbian, and the Russians didn't conspire against them, that is. It all turns out fine in the end, though.
Reversed with Ron and Hermione. By Prince, Ron's technically a jock, and Hermione's still a geek. Not to mention Cormac, who is also a good-looking Quidditch player (though it's subverted in that Hermione thinks he's an idiot and only dates him once, to annoy Ron). Before that there was also Goblet of Fire, when the popular and athletic Viktor Krum is smitten with Hermione.
Rowling states that if Snape had never gotten into the Dark Arts and the Death Eaters, a romantic relationship would have likely developed between him and Lily.
Percy Jackson and Annabeth Chase in Percy Jackson and the Olympians. Again, Percy is not so much a geek as he is the new guy. Once he gets used to being at Camp Half-Blood, they settle into a more Battle Couple style of coupledom. Arguably inverted, since Annabeth's much more of a geek with her architecture than Percy, who starts to develop into more of a jock with his swordsmanship.
In Rachel Flynn's Messing Around, Thadeus talks about how his similarly geeky father is writing a romance novel. From the brief excerpt we see of it, the novel invokes this- with no small amount of Wish Fulfillment on the side. (In this case, it's the hot girl who notices the clumsy, bookish guy, not the other way around.)
Live Action TV
The entire Fan-Preferred Couple shipping of manly series lead Oliver Queen with geeky, perky computer girl Felicity Smoak on Arrow is pretty much based and built on this trope.
In One Tree Hill the character of Mouth—who used to be geeky comic relief—gradually evolved into a full-fledged character. Mouth throughout the years has not not only became one of the more popular kids but is also given plenty of hot girlfriends, one being an office affair with his boss.The writer admits that he feels a lot of sympathy towards kids like Mouth and even claimed the character resembles himself in some ways. And now Mouth is in a relationship with Millicent (who's somewhat geeky herself.)
The final pairings of Power Rangers Jungle Fury (Theo/Lily and Dominic/Fran) went along these lines as well, both of the alternative options (Casey and Maryl respectively) being more conventionally "normal" compared to their rivals.
Jerry Seinfeld regularly brought home supermodels. One could at least argue a funnyman with a reasonably successful career could do well.
When asked how George Costanza could get so many attractive women, Jason Alexander put it down to persistence (indeed in one episode, George's persistence makes one woman who previously wasn't interested at all want to date him).
Kramer, an unemployed, slightly shady Cloud Cuckoo Lander who woos women (including nuns and lesbians) into his embrace with the power of Kavorka.
Fargo the ubergeek in Eureka hooks up with two geeky girls. The first is Claudia. He impressed her by turning one of their artefacts into a lightsaber. The second is Holly, a fellow computer geek at Global Dynamics.
The entire premise of the live-action Japanese series Densha Otoko which chronicles the attempts of a weakling, nerdy, geeky, otaku-type guy who is trying to date a beautiful woman with the assistance of a messaging board on the internet, after he saved her from a drunk guy on a train. Based on a real story. Also available in manga form as train_man.
Married... with Children originally had Marcy and Steve Rhoades. She was hot, he was a nerd. Later reversed when Marcy married the amazingly hot Jefferson Darcy
This was, in fact, the central gimmick of the 1992 FOX series Flying Blind, in which Neil, a shy, repressed nebbish played by Corey Parker, somehow fell into a mutually fulfilling relationship with Alicia, an incredibly hot bohemian woman played by Tea Leoni. The series slightly bucked the trope by keeping the couple unmarried, which allowed the constant implicit tension of the possibility that Alicia would come to her senses and leave him.
On Stargate SG-1, Daniel Jackson has the best romantic record in the group. He picked up a wife in the original film, and also spent over 50 years with Vala in the finale.
Rodney and Jennifer Keller in Stargate Atlantis. When he takes Keller to a science presentation on Earth, his colleagues initially think she's his (also attractive) sister. On the flight back, she is the one who suggests they join the Mile-High Club, although it could've just been to shut him up.
On Bones Dr. Hodgins starts out as a complete geek who is totally in love with, out of his league, Angela. Despite her initial refusal at his advances she finally agrees to go out with him. The two eventually go on to get married and have a child.
Palaeontologist Ross and the socialite Rachel are the show's lead examples, and had this dynamic going back to high school where he was the nerd and she was the Lovable Alpha Bitch, who barely noticed him. As adults she's a Spoiled Sweet former Gold Digger who eventually goes to work in fashion and he becomes a university professor.
The producers did admit that the character designed to be the group geek was actually Chandler, not Ross. However, Chandler heavily downplays his job, skirts over his geekier hobbies (such as his Star Trek obsession), and never discusses his education, leaving Ross to be the main target for ribbing. The few comments he does make about his career make it obvious he's a statistician by training and an IT statistics specialist by career. The entire gang act as though Chandler is far beneath Monica and that Monica could do far better than settling for him. At one point Phoebe and Rachel even try setting Monica up with other men. Chandler himself has such huge self-esteem issues that he's as convinced of his unworthiness as the rest of the gang. The oddity of the gang's attitude about this is very stark when considering the following: in-universe, Chandler is considered the funniest of the gang, the sweetest (and "softest") of the guys, has a very successful career and is also handsome to boot (in-universe, he's universally regarded as "cute"). This actually makes him the best catch out of the entire cast. What makes the pairing work, is that although Monica isn't a traditional 'geek', she's the most intelligent of the girls and her highly neurotic nature (playing with her label maker, categorizing her towels and ironing wrapping paper, are a only a few examples) offsets Chandler's nerdiness. So their acceptance of each other foibles is a two way street and very believable. Plus, only Rachel and Phoebe imply Chandler doesn't deserve Monica and that seems motivated jealousy. The rest of the gang acknowledge Monica is more attractive but know Monica can be as quirky as Chandler at times. As the relationship progresses you see Chandler grow more confident as she builds up his self-esteem. By the end he's more open about his geeky habits (like his love for musicals) and clearly happier in such a fulfilling relationship. His crippling insecurity mostly stems from his own self-doubt and previous failed relationships.
A rare male-hottie/female geek version of this trope with Chloe Sullivan and her crush on Clark.
And then they bring it back to make geek/female hottie with her relationship with Jimmy Olsen. Notably, this is also how the Clark/Lana relationship was portrayed in Season 1, with geeky outcast Clark pursuing uber-popular Lana and trying to show her that he was more worthy than her then-current Jerk Jock boyfriend Whitney.
In her very first episode, Lois notes the kind of guy she's attracted to: "Give me a nerd with glasses any day." Martha helpfully replies "Clark has many sides."
Charlie and Amita on NUMB3RS. It's true she's a computer geek, but she's a smoking hot computer geek.
Chuck and Sarah (and Jill and Lou and Hannah...) on Granted, he's Hollywood Homely / a Hollywood Nerd, but still he's an ubergeek with a dead-end job at a big-box electronics retailer...
In another episode, one of Sarah's former classmates (also a hottie) shows up with a nerd husband. However, it's revealed that she doesn't much care for him and only married him because she reasoned that nerds are the ones who end up making the big bucks (she thinks that Sarah's doing the same with Chuck). She got really pissed off when he decided to do the right thing instead of making money. Cue the Designated Girl Fight.
There's also Morgan and Alex (pissing off Casey to no end)... and Morgan and Carina (although it was just one night).
Arguably inverted in Sabrina the Teenage Witch with Sabrina and Harvey. It's true that the pretty, blonde, funny, Sabrina is practically the poster girl for Cool Loser but she does have a lot of dorky interests (science, maths, high school journalism...). Harvey on the other is a popular jock (though not a jerk). This is reversed in the animated series, where Harvey is a nerdy weirdo… who has girls fighting over him anyway.
In CSI: NY it's an inversion as female geek hottie Lindsay ends up with male hottie Danny.
The Reality ShowBeauty And The Geek reinforced why this could be Truth in Television. By the end of the show first season, many of the Beauties were gushing about how their Geek was one of the best guys they'd ever met, when only one or two of said Geeks were conventionally good looking (though, admittedly, none of them were particularly gruesome either). One "beauty" and one "geek" had a brief romance during their season.
Leonard and Penny. However, in earlier seasons, Leonard was paired with the equally geeky Leslie Winkle, but it's Penny he's fixated on. They're currently in full-on Will They or Won't They? mode.
Averted with Howard Wolowitz, the show's resident Casanova Wannabe who regularly strikes out with most of the hot babes he tries to pick up, before hooking up with the utterly Adorkable Bernadette.
Played with extensively with Sheldon, who in one episode was shown to have a tendency to attract pretty grad-students with his intellect alone (some may be just from his Child Prodigy status). But given that he is generally Asexual he ends up as a Clueless Chick Magnet. Later on in the series he finds a Distaff Counterpart in Amy Farrah Fowler, similarly brilliant with just as many if not more social awkwardness. After an initial She's Not My Girlfriend phase, they later make a Relationship Upgrade as they are the only two people who could possibly tolerate each others idiosyncrasies.
In 3rd Rock from the Sun, Officer Don Orville (A really big dork of a small town police officer) ends up with Sally Solomon, who is supermodel beautiful. Ironically, she loves him because she thinks he's everything he says he is, despite the fact that as a professional soldier, she should be able to tell he's not. Or perhaps it's just the fact that whenever the two are alone, the tone of the show switches to Film Noir. Plus they figured out that he has to always be in uniform too.
In Freaks and Geeks, Sam Weir is finally able to start dating his dream girl, cheerleader Cindy Sanders. Unfortunately, she turns out to be somewhat of a Bitch in Sheep's Clothing. Less a Bitch in Sheep's Clothing as they just found they had nothing in common. She decided to give him a chance because he was a Dogged Nice Guy and her last boyfriend was a Jerk Jock, assuming that meant he would just do whatever she told him. When he dumps her (both because of how she treated him and because they have nothing in common), she agrees they don't have much to talk about, realizes she treated him poorly, apologizes, and asks if they can still be friends because he really is a nice guy who deserves better.
Primeval has Connor and Abby. Nerdy, awkward Connor Temple and hot, ass-kicking Abby Maitland.
On 15/Love Rick was socially inept Butt Monkey. Cassidy was a very attractive British tennis star.
Sav Bandhari tends to be a bit socially awkward, but ends up having a rather storied love life.
Liberty and Toby were both this trope in the earlier seasons too, although Toby was gradually Demoted to Extra.
Subverted in 90210. Beautiful Lovable Alpha Bitch Naomi falls for Hollywood Nerd Max but (to her amazement) he's initially disinterested because he views her as a shallow airhead. She has to work hard to get him to realize she has Hidden Depths and the show makes it clear that Max has had a healthy romantic life before they even met.
Saved by the Bell : The ultimate geek, right down to his nickname, Samuel "Screech" Powers had several one-episode love interests, often played by extremely beautiful actresses (Hillary Danner, Emma Caulfield, Christina Moore, Marnette Patterson). In one story arc, Screech had a recurring girlfriend named Alison, played by the lovely Clare Salstrom. Even his "nerdy" girlfriend, Violet, was played by Tori Spelling, although she wore thick glasses and a dorky hairstyle and clothes for the role.
Freddie in iCarly. Is quite the geek, especially in the episodes he is paired with Sam. With Carly it is more a geeky turn-on.
Alan Harper on Two and a Half Men ends up with several hotties over the course of the show(though not as many as Charlie of course).
House of Anubis so much for both Fabian (the shy, nerdy guy who can hardly talk to people on some occasions without stammering) AND Alfie (the class clown obsessed with aliens, zombies, ninjas, etc.) Fabian has had two girls desperate for his attention and love, and Alfie had not only dated the beautiful blonde, but also has two other romantic interests as well. Seems the ladies in the house love the geeks.
The song "The Geek Gets The Girl" by American Hi-Fi is made of this trope.
Played with in David Bowie's Short FilmJazzin' for Blue Jean. His Adorkable protagonist Vic, who tells his frosty dream girl a Celebrity Lie about knowing a handsome rock star (also Bowie), loses her to said star, whom she knew all along. At this, Bowie breaks character and objects to the "too obvious" unhappy ending.
The trope is played with slightly cynically in later Ménage à 3 strips, as hopeless geek Gary is frequently pursued by various members of the comic's stunningly attractive female cast (plus at least one gay guy and one transsexual). However, not many of them like him for his geekiness; their reasons include his blushing, bumbling cuteness, his supposedly glamorous status as a (wannabe) artist, and his fabled skill at cunnilingus.
In Thalia's Musings, Hephaestus tries to invoke this in his marriage to Aphrodite. It doesn't work. After his divorce, he inverts the trope by falling for Aglaea, a science-obsessed demigoddess who's had a crush on him for awhile.
In the Whateley Universe story "The Big Idea", Reach is enamored with cute scientist Spark who is European and doesn't see him. (He has a bad Kentucky accent and wants to join the Intelligence Cadet Corps.) He eventually gets the girl, but by then they have both been transmogrified so they're both much better looking.
The happiest married couple in the Global Guardians PBEM Universe is mathematics professor-turned-mystic-superhero Moishe "Doctor Kabbalah" Rothstein (5'8, skinny, glasses, jewfro) and his wife, the smokingly hot former supermodel Greta von Hapsbach-Rothstein (6'1", statuesque Nordic goddess).
Inverted in The Guild, where the geeky Codex tries to get with the attractive stuntsman Wade. Of course, Codex is played by Felicia Day, so it's a clear case of Hollywood Homely. Played straight with Zaboo and Riley, although, technically, Riley is also a gamer (let's not get into an FPS vs. MMORPG discussion).
Gerald and Phoebe from Hey Arnold! is one of those rare moments that the girl is the "geek" in question here.
The writers of the RugratsAll Grown Up! series tried to avoid flat out confirming certain pairings (most likely trying to avert a Broken Base) but Ship Tease did happen nevertheless. One example of a pairing that got Ship Tease that fits with this trope is Chuckie and Angelica. (Which of course has received even more attention from fans in fan work.)
Dr. Walter Hartford of Galaxy Rangers fits a lot of the usual definitions for a geek; highly educated, computer hacker, fast mouth, and fond of pop culture references. Princess Maya didn't think much of him at first, and was more attracted to Gooseman. Then, Doc turned on the charm...made contact with an alien computer that was protecting the planet, and handed a Crown Empire spy his ass in a swordfight. Maya never mentioned Goose again!
Notably played with and then averted in W.I.T.C.H. between Irma and Martin. Early on it seems to be setting up to invoke this trope, as Martin is smitten and Irma rebukes him at every turn. She eventually (and reluctantly, as it was necessary for a distraction) goes on one date with him and is miserable the whole way through. Later though she is visibly jealous when he is interested in someone else. By the end of the series, she's the only main character not in a relationship and her and Martin have settled into a mutual quasi love/hate friendship. Irma took Martin on a Not a Date in the first season as a distraction and while it wasn't really fun for her, she still gave him a peck on the cheek at the end of it. In the comics where she actually gave him a Just Friends speech, Martin then had a cute French penpal that visited and seemed totally enamored of him with the feeling being apparently mutual; Irma quickly turned into a Clingy Jealous Girl while denying it to her amused friends. In one issue a possible (and likely) future version of Martin is All Grown Up with a significant amount of Ship Tease with future Irma. It's more like Irma doesn't want to give the geek a chance while giving him just enough to keep hoping.
Doug: Athletic Patti and the clumsy, shy, Adorkable title character.
Subverted in Daria. Quinn gets an older, brainy tutor named David, and begins to become smarter as they work together over the summer. She falls for him and asks him out, but he turns her down, noting that she lacks the "depth" he looks for in a girl. Quinn is heartbroken, since David is pretty much the only guy to ever turn her down (or for that matter, the only one she ever seemed to like for more than just looks or popularity).
Netscape founder Jim Clark is married to a supermodel.
Filmmaker and self-professed comic book/sci fi geek Kevin Smith and his wife Jennifer, who is absolutely gorgeous. In fact, Smith wrote in his book that he fervently hopes their daughter Harley grows to be as tall and shapely as her mother, thus sparing her from what he goes through with his weight. Smith also theorized that geeky and/or chubby men are better catches, as they're much more willing to go the extra mile for a woman.
Mistress Matisse's column in the Seattle Stranger mentions that geeks and nerds make up a frighteningly large percentage of the kink community, and advises those looking to mingle among them brush up on their Robert A. Heinlein and watch some of Joss Whedon's work.
James Madison and Dolley Madison. She was 17 years younger than him.