25 TV Characters Who Dated Out Of Their League

These guys excelled when it comes to "dating up."

September 27, 2012
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Love may be blind, but most people aren't, so it's weird when you see two people together who are physically out of each other's leagues. It's true on the street, in real-life, and when actors portray mismatched lovers, as on the new ABC horror drama 666 Park Avenue, where bald, old Terry O'Quinn plays a building owning who somehow has bagged a hot, sophisticated, and younger wife played by Vanessa Williams.

One could say that someone who's dating a physical superior simply lucked out, but remember: In every couple where one person is dating up, there's always the fact that the other person is dating down. With a skeptical eye to 666 Park Avenue, which premieres Sunday at 10 p.m., Complex remembers some of the boob tube's oddest couples: 25 TV Characters Who Dated Out Of Their League.

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Written by Tanya Ghahremani (@tanyaghahremani)

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Penny and Leonard, The Big Bang Theory

Penny and Leonard are the poster children for a couple so out of each other’s leagues that they’re hardly playing the same game. The plot of the show is straightforward: a group of geeks luck out with a hot neighbor, Penny, played by Kaley Cuoco.

The least geeky of the bunch, Leonard (Johnny Galecki), is immediately, and understandably, infatuated with her. Penny is attracted to Leonard presumably because he’s different than all of the other muscle-men Hollywood types that she’s dated before. Totally stable foundation for a relationship? In series creator Chuck Lorre’s world, yes. But hey, that guy also cast Charlie Sheen in Two and a Half Men.

Cordelia and Xander, Buffy the Vampire Slayer

Don’t get us wrong—Cordy (Charisma Carpenter) and Xander (Nicholas Brendon) were great while they lasted. Opposites sometimes attract, and these two couldn’t have been more different from one another when they first met. It made for an interesting dynamic between the two, and quite frankly, gave both characters, especially Cordelia, depth and layers where they were sorely needed.

That being said, it never made any sense. She was the smart queen bee with her own personal minions known as the “Cordettes,” and he was a lower middle class secret country music fan with a C average and no special powers to speak of. Maybe if he had some kind of magic spell he'd cast on her we could comprehend.

Cheryl and Larry, Curb Your Enthusiasm

One could argue that Larry David, while not a looker, isn’t exactly a bad catch. He created one of the most successful shows (Seinfeld) of our time, is filthy rich, and funny, all of which helps balance out his rather meh looks and slovenly appearance.

What ends up tipping the scales way, way, way in Cheryl Hines’ favor is Larry's complete lack of social grace and etiquette. He thinks he knows the way the world should be, and though he's often right, he has no clue how to interact with people so he doesn't come across as an asshole. In fact, it’s so bad, one has to wonder how anyone is still his friend anymore, let alone eager to work with him. Cheryl, a much younger, attractive blonde, is a perfectly pleasant person could have done much better.

Puck and Lauren, Glee

In the history of high school, the popular asshole jock (Mark Salling) has never gotten with the misunderstood tough chick with a weight problem (Ashley Fink). Self-help books preach that it’s what’s on the inside that counts and everyone should reach for the stars, but still, it never happens. Glee is, like, so revolutionary, you guys!

Liz and Dennis, 30 Rock

30 Rock likes to paint Liz Lemon (Tina Fey) as a full-on geek in every facet of her life—love life, work life, social life, family life, you name it. The majority of the jokes on the show have a sour center to them in the form of Miss Lemon herself.

If you look closely at Liz’s character, though, it’s fairly easy to see that this shouldn’t be the case. Socially inept as she may be, she still has an outstanding position in one of the biggest television networks in the world, she’s the protege of Jack Donaghey, and she once had sex with James Franco and his anime body pillow, Kimiko. Additionally, and probably above all, she’s a smart woman. All things considered, Liz Lemon is a catch.

This is what leads us to her relationship with Dennis Duffy (Dean Winters). When the series began, he was Liz’s boyfriend, the last remaining Beeper salesman in NYC (dubbed “The Beeper King,” as the old one perished), and seemingly more of a leech on Liz’s life than a romantic partner. He’s not smart and he’s manipulative, which makes little sense considering that one needs to possess intelligence to manipulate others. Financially, he's makes nowhere near was Liz does. Obviously he's the real lemon.

Liz and Drew, 30 Rock

Liz may be smart and successful and all that, but come on, this is the same man who plays Don Draper we're talking about. The show even dedicated an episode to showcasing exactly how many levels of different they are, aptly titled "The Bubble," In it, Liz forces Drew to see that he's been living in a so-called "bubble" for all of his life because he's attractive, and this has allowed him certain advantages over people who look like, say, her.

He, at first, doesn't think he wants the special treatment, but once he begins to lose at tennis and not get complimentary appetizer samplers at restaurants, claims that he wants to live in his bubble because it's easier that way. And the world will let him, because he's Jon Hamm.

Summer and Seth, The O.C.

It’s a trope loved by TV shows from sitcoms to supernatural shows to teen dramas: The pseudo geek, in this case Seth (Adam Brody), admires and idealizes the hot girl in school, in this case Summer (Rachel Bilson), from afar for ages. Eventually some weird happenstance brings them together, and something will possess the girl to give the dude a chance even though she’s supposed to be shallow with only thoughts of Channing Tatum and handbags in her pretty little head.

Generally, there will be some defining moment in their relationship that shows the popular girl really does have a deeper side. If you’re not aware, that basically just described seasons one and two of this oh-so-inventive show.

Serena and Dan, Gossip Girl

See Summer and Seth, only replace Seth with an angst-filled, sub-par Brooklyn writer obsessed with waffles named Dan (Penn Badgley), and Summer with a leggy, coke-addicted Manhattan blonde named Serena (Blake Lively). Considering Josh Schwartz created both The O.C. and Gossip Girl, this really just attests to his creativity, doesn’t it?

Chuck and Sarah, Chuck

To be fair, Sarah (Yvonne Strahovski) actually was relatively geeky and unattractive in high school, and it was only when she joined the CIA that she turned hot, because apparently the U.S. government employs stylists and makeup artists.

When nerdy Chuck (Zachary Levi) meets her, however, he doesn’t know this; he believed she was just a hot blonde who had a thing for computer geeks. Here’s the thing, though: Even if she was plagued by ghosts of her geeky high school past, years have passed since then, and Sarah’s presumably grown and changed as a person because of the things she’s experienced on the job. And we’re supposed to believe that a video game-obsessed Geek Squad manager was enough to catch her eye?

Oh, hey, Josh Schwartz, we see your name listed there as co-creator. It all makes sense now.

Mike "Probie" and Theresa, Rescue Me

Rescue Me was never a show filled with logical romantic pairings, but Probie (Michael Lombardi) and Theresa (Ashlie Atkinson) made the least sense of them all. Here’s a guy who’s, though not very bright, is a New York City firefighter capable of getting any girl he wants in the tri-state area.

He seems to be well aware of this the second he lays eyes on Theresa, the homely-looking chick his mom set him up on a date with. The date doesn’t go well, and at one point Theresa accuses him of considering ditching her before they’ve even had dessert. Probie, this is the part of the horror movie where everyone’s telling you to run. But because he is a simple-minded man, he has sex with her later that night for the hell of it, and it’s good—so good that suddenly they’re dating.

Things seem to be going well until it’s revealed that Theresa has a few deep-rooted issues of her own: She’s bulimic, has serious body-image and self-esteem problems, and is absolutely convinced that her relationship with Probie is destined to go nowhere because he’ll inevitably get bored with her and move on to greener pastures.

At this point, Probie is completely smitten with her, and heartbroken when she breaks up with him for some geek who has no lines but looks like he speaks Klingon as a second language. The only thing worse than dating someone so out of your league is mourning someone so out of your league. Live and learn, Probie.

Rachel and Ross, Friends

Rachel (Jennifer Aniston) and Ross (David Schwimmer) may have been the couple of all couples on this show, but let's be real: If this weren’t a sitcom, so much of the show would have gone down differently.

One, they would not have all lived in gigantic Greenwich Village apartments on their salaries. Two, Ross, a geeky, neurotic paleontologist, would never have landed the affections of spoiled, hot Rachel, who was born with a silver spoon in her mouth. Three, seriously, look at their apartments—that would never happen!

Carrie and Doug, King of Queens

The only thing sitcoms love more than pairing a geeky guy and a hot girl together against all odds? Pairing an inept yet lovable fat guy with a hot wife. Of course, no one would watch if the chick wasn’t hot, right? That would be against the rules of television. Can’t help but wonder: Over the course of this show, were we supposed to be waiting in suspense to see what would kill lazy husband Doug in first, his arteries or his wife?

Lip and Karen, Shameless

Physically, Lip (Jeremy Allen White) and Karen (Laura Slade Wiggins) look great together. She’s attractive, he’s attractive—attractive people attract, and as Jesse Pinkman would say, yeah bitch, science.

What makes these two out of each other’s leagues, or specifically Karen out of Lip’s league, is the fact that Lip is a genius, and over the course of their relationship Karen does nothing but attempt to hold Lip back for her own selfish reasons. He has the intelligence to escape his dysfunctional family and impoverished reality and be a successful member of society, while Karen is likely a borderline psychopath with Machiavellian tendencies who only cares about money and sex.

For some reason, Lip, who can get plenty of girls, is in love with her, and dropped out of high school during his senior year because she was pregnant and there was a small, small possibility the child could be his (she's the neighborhood bike). When it turns out that it isn’t his child, he still remained lovesick over Karen. Oh, yeah, and did we mention she had sex with his dad, filmed it, and posted it on the Internet for the world to see in an effort to get back at her own father? Stay classy.

Lizzie and Charlie, Californication

Charlie (Evan Handler) is a nice enough guy. He’s got a great job as a Hollywood agent (he’s got money) and is a good friend to Hank. But as far as looks go…he’s not exactly calendar material. Which is why it’s super weird when his kid’s hot nanny, Lizzie (Camilla Luddington), seems to show a genuine interest in him, sexually. But hey, people have their kinks, and he’s rich. Maybe she’s just into bald dudes. Stranger things have happened, right?

Wrong. As it turns out, Lizzie was just after Charlie because he’s an agent, and she, like the majority of gorgeous 20-something women who move to L.A., was looking to make it as an actress in Hollywood. What started out as a “is she really going out with him?” relationship that would undoubtedly make Joe Jackson proud quickly turns into just the opposite: Is he, the sweet, lovable, Charlie, really going out with her? Fact of life: Hot people make other people stupid.

Cersei and Robert, Game of Thrones

Yeah, he’s the King, and she’s a Lord’s daughter who thinks her twin brother is her soul mate, but still—look at her. Now, look at him. Back to her. Back to him. See what we’re getting at? Furthermore, Cersei (Lena Headey), with all her faults—namely, the fact that she’s an incestuous psychopath—is a BAMF, and she’s a Lannister, which means a hell of a lot. Additionally, she hated Robert Baratheon (Mark Addy) with all of her cold, dead heart, so there’s that as well.

Izzie and George, Grey's Anatomy

A world where someone who looks like Izzie (Katherine Heigl) and someone who looks like George (T. R. Knight) are friends is a normal, but a world where someone who looks like Izzie and someone who looks like George hook up could only exist in a Shonda Rhimes series. And so, here we are.

We’d say that the moment when these two drunkenly hooked up and apparently had awesome sex was the moment the series jumped the shark, but this is the same show that had a icicle randomly fall from the sky and impale one of the doctors because shit happens. The only realistic thing about this relationship? When they had sex for the first time without the beer goggles on, it was awkward has hell.

Laura and Urkel, Family Matters

How do you know when show writers have run out of plot ideas? When they think it’s a good idea to pair the most annoying nerd character ever written on television with the girl (Kellie Shanygne Williams) who spent most of the series denying his advances and being disgusted with him, that’s when.

Another indicator? When Urkel (Jaleel White) creates something called “cool juice,” drinks it, and turns into a suave alter-ego named Stefan. And also that time he went to space. But hey, we won’t go into that in an effort to preserve everyone’s sanity, so let’s just keep discussion about this couple at a good old WTF.

Donna and Eric, That '70s Show

Donna (Laura Prepon) and Eric (Topher Grace) never made sense to us. He was a slight, Star Wars-obsessed nerd, she was an intelligent, strong, rocker chick who was nicknamed “hot Donna” during her internship at a radio station.

Apart from their shared interest of smoking weed together with their friends and a secret love of the band Styx, these two were on completely different wavelengths. Sure, you could get all sappy and say that they truly loved each other and all that stuff, but how about we don’t and say we did?

Jackie and Fez, That '70s Show

Throughout the series, Jackie (Mila Kunis) is portrayed as a self-obsessed, shallow girl with a bubblegum idea of what a romantic relationship should be. She dates the likes of dumb hottie Kelso and bad boy hottie Hyde, but in the end, somehow falls in love with the dorkiest of the group, her quasi-stalker Fez (Wilmer Valderrama).

Her excuse? She wants to be with someone who's as obsessed with her as she is with herself. There’s no reason that she shouldn’t believe she could do better than him; she knows it because she has done better than him. If the focus had to be squarely on her, perhaps she should've just dated a mirror and a vibrator.

Gloria and Jay, Modern Family

Just look at that photo. Do we need to say more? OK, we will, but the physical disparity between gorgeous, young Gloria (Sofia Vergara) and her grouchy, geriatric, rich-guy husband, Jay (Ed O'Neill), is pretty obvious. Love is blind, but even Stevie Wonder would agree that Gloria could do better for herself, even just amongst the ranks of old rich dudes.

Ethel and Fred, I Love Lucy

What makes these two out of each other’s leagues is mainly derived from the actual actors who portrayed them—the animosity existing between actress Vivian Vance and William Frawley is no secret. Vance was ticked off that an actor so much older than her, specifically 22 years, would be cast as her husband, and once Frawley referred to Vance as a “sack of doorknobs.”

On screen, Ethel and Fred’s relationship was often portrayed as a classic sitcom marriage—lazy husband, whiny wife (sound familiar?)—and the two had a noticeable amount of comedic chemistry, but that still doesn’t change the fact that Ethel was married to a man old enough to be her father. That’s a deal-breaker, ladies.

Lindsay and Tobias, Arrested Development

Lindsay Bluth (Portia de Rossi) is gorgeous, blonde, and…. OK, that’s about the point where her good traits end, but still there's no way she should be married to Tobias Fünke (David Cross), a balding moron who believed that, since he was licensed as a analyst and a therapist, a good way to describe his job would be “analrapist."

It could be said that it’s actually Tobias who deserves better, considering that Lindsay only dated and married him because she wanted to spite her parents, and she believes that he’s gay, but the key word there is that it could be said. It could be, but it won’t be. Girlfriend could have done so much better.

Jonathan and Rose, Bored to Death

Neurotic, struggling author Jonathan (Jason Schwartz) had dated many fine women before he met Rose (Isla Fisher), but that doesn't change the fact that he's a mostly failing, worry-wart scribe who has to moolight as a detective to make ends meet. Rose, on the other hand, while not without her quirks, is gorgeous, smart, funny, and could absolutely do better than a guy who’d rather sit and drink white wine while reading mystery novels than work on improving his life.

That’s not the weird part of their relationship, though. While on a case, Jonathan discovers that he and Rose are test-tube babies, born to separate mothers from the same father who, er, contributed a lot to a sperm bank. He learns that she’s biologically his half-sister but, because he’s well aware that she’s out of his league and likes dating her, doesn't inform her. The weirdest part: HBO declined to renew the series after the season finale in which this all comes out, so the two are presumed to have ended up together.

Sam and Cindy, Freaks and Geeks

In the beginning, geeky Sam (John Francis Daley) is hopelessly in love with Cindy (Natasha Melnick), and who can blame him? She’s a beautiful, popular cheerleader and he’s a hormonal teenage boy. Of course he's in love with her.

When she develops feelings for him and they start dating, though, Sam discovers how boring, self-obsessed, and shallow Cindy is and realizes that he's the one who could do so much better. You see, being out of someone’s league isn’t always about looks. Sometimes it’s about have some semblance of self-respect, and realizing when a good looking person is just that: A good looking person. Nothing more, nothing less.

Sally and Jemaine, Flight of the Conchords

Anyone Jemaine (Jemaine Clement) or bandmate Bret (Bret McKenzie) dated in Flight of the Conchords was out of their league, since they were both struggling singers from New Zealand without a penny to their name, but Sally (Rachel Blanchard) and Jemaine’s relationship stuck out the most.

She was substantially better looking than he was, and during the course of their relationship, Jemaine fantasized about what their married life would be like, in a delightful little song called “Business Time,” which detailed how they’d have great lives, and have sex for two minutes every Wednesday. Anyone deserves better than that, especially someone who looks like Sally does.

Runner-up for this slot? Prior to dating Jemaine, Sally was involved with Bret. Yeah. The world of television can sometimes be very kind to the underdogs.