25 TV characters who dated people out of their league

Ah, romance. It’s the cherry on top of the human experience. That’s probably why half the fun of tuning in to watch our favorite TV shows, is watching two characters fall in love and eventually get their happily ever after. Whether they’re heroes or villains, romance is what drives characters into making grand gestures, acting foolishly, and even committing crimes – all of which make for good television.

The reality is, people love watching heart breaking love stories on-screen – whether it’s shedding a tear (more like crying uncontrollably) for Jack and Rebecca in This is Us, hoping that Claire and Jaime find their way back to each other in Outlander, or root for Sheldon and Amy on their anticipated wedding day. Many TV couples consist of just two beautiful people who naturally come together, and we’re here to say – that’s boring! (Sorry, Derek and Meredith). In real life, people don’t always end up with someone who’s just as good-looking as they are, but instead rather choosing their life partner based on more important criteria, like, say, their personality.


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They say love is blind, but being out of one’s league isn’t all about appearances. It can also be about a good person who dates-down someone who treats them badly, or who’s just plain evil. Television romances may not always be realistic, but sometimes there’s a lot to be learned from them about choosing your life-companion. In the past, people could only swoon over characters in romance novels like Pride and Prejudice or Jane Eyre (which they still do), but television undoubtedly takes it to a whole other level. Television shows do a great job in tantalizing their poor viewers, sometimes for a few long seasons, in anticipation for their favorite will-they-won’t-they couples to just get together already.

Of course, it’s mostly fun (and funny) to watch when the couple is horribly mismatched or otherwise unconventional. We just love watching geeks end up with the girl of their dreams, and seeing how love conquers all, the heart wants what it wants, and all the rest of these sappy clichés. Some of these couples don’t only prove that literally any two people can come together, but also inspire other people to go for what they want, and not be afraid of rejection. Other TV couples make us wonder how on earth they’re still together. Keep reading to see which characters from which shows made the list.

Alan and Lyndsey, Two and a Half Men

It is pretty unclear why Lyndsey dates Alan in the first place. Alan is pretty much a failure at everything he does, and spends his life mooching off his brother and anyone he can. Lindsey can obviously do much better than him. But she dates him nonetheless, and sticks with him even after he accidentally burns her house down, and on her birthday – “thoughtfully” gives her some jewelry that he stole from his ex-wife, Judith.

Ross and Rachel, Friends

Ross and Rachel are undoubtedly one of the most beloved couples to ever grace our television screens. But it’s no secret that Ross, or “Monica’s geeky older brother”, always held a torch for the most popular girl in high-school. While Ross still remains a geek as a grown-up, he eventually gets Rachel to notice him, and she realizes just how wonderful he is. The on-again-off-again couple made fans everywhere root for them – whether if they were, or weren’t, on a break.

Dan and Serena, Gossip Girl

Dan had a thing for it-girl Serena, but didn’t think the popular rich girl would go for a Brooklyn misfit. Apparently, Dan was just the kind of guy that Serena always wanted, and she ends up asking him on a date. Even though they have a rocky relationship (and things get a little weird when their parents date each other as well), Dan and Serena end up together and are ultimately one of Gossip Girl’s favorite couples.

Cersei and King Robert, Game of Thrones

Cersei Lannister is definitely no angel (and by no angel we mean a full-on psychopath), but that doesn’t mean she deserved a husband like Robert Baratheon. Yes, he was the king, and he might’ve been more handsome in his younger years – but that doesn’t make up for his tendencies to drink heavily, feast with gluttony, gamble, and neglect his gorgeous wife. On their wedding night, he even drunkenly mistakes Cersei to be Lyanna Stark. If that’s not enough to turn a woman’s affection to hatred, we don’t know what is.

Xander and Cordelia, Buffy the Vampire Slayer

Although she evolves into a mature grown woman who dedicates herself to helping others, Cordelia is first introduced to us as a rich, spoiled, stuck-up, popular high-school girl. She belittles Xander and his friends, considering them to be losers. But the heart wants what it wants, and she still falls in love with the geeky Xander, despite peer pressure from her popular friends. Although they were worlds apart, their love-hate relationship was truly a fan-favorite on the show.

Liz and Dennis, 30 Rock

Liz Lemon is a talented writer, who has an executive position at one of the major television networks. She’s a real catch. So we still ask ourselves why she ever dated Dennis Duffy, the last Beeper salesman in New York. This unimpressive man is pretty much a leech who feeds off her life, and doesn’t make up for it by being a good boyfriend either. And yes, he is giving her a noogie in that picture.

Elaine and Puddy, Seinfeld

Elaine Benes is an intelligent, and mostly classy woman. So her attraction to David Puddy – an auto mechanic who’s not exactly the sharpest tool in the box – is pretty curious. Elaine finds herself dumping Puddy for hilarious reasons (like painting his entire face for a Devils game), and repeatedly getting back together with him for even funnier reasons, like when she needs help moving a bureau. In the end, when Elaine goes to prison, she tells Puddy not to wait for her, to which he casually replies, “Alright.”

Alan and Kandi, Two and a Half Men

Don’t get us wrong, we’re not saying that Alan is bad looking. But even if you count-out all his other flaws we mentioned earlier, that still doesn’t explain how he landed a girl like Kandi, whom we can only describe as “va-va-voom”. Alan was so happy that he finally caught a lucky break, that he spent all his money on the twenty-two (and a half!) year old, and then spontaneously married her in Vegas. Of course, she later divorced him and left him with nothing, but that’s just Alan’s life.

Selina and Andrew Meyer, Veep

Just because Selina Meyer is the Veep, or the President of the United States, doesn’t mean she can’t date. And while she’s dated pretty interesting characters (we’re looking at you, Ray the personal trainer), the one who really takes the cake is her ex-husband, Andrew Meyer. Selina can’t help her attraction to Andrew, who engages in unsavory business ventures, and constantly betrays Selina’s trust. And if all that weren’t enough, he didn’t even vote for Selina in the election.

Chuck and Sarah, Chuck

When Sarah walks into the Buy More and approaches the Nerd Herd stand, Chuck is practically floored. Who can blame him, when she’s so gorgeous? Chuck is the ultimate gaming-obsessed computer geek, but let’s admit it, he’s not so bad looking either. Throw in a little danger (and being forced to share a bed together on a mission), and the two finally became a thing, making geeks around the world cheer as Chuck got the girl of his dreams.

Ray and Debra, Everybody Loves Raymond

Ray and Debra are undoubtedly a good couple with a beautiful family. But the woman should get a medal for everything she has to deal with when it comes to Raymond. He does nothing around the house except sit on the couch and watch TV, he repeatedly discloses every detail of their personal lives to his family, and almost never has the courage to take her side when his mother insults her (which happens in almost every episode). All in all, the woman is a saint.

George and Izzie, Grey’s Anatomy

Izzie and George (may he rest in peace) made sense as friends, but never as a couple. Izzie paid her student loans by modeling for Bethany Whisper – which is presumably Grey’s Anatomy version of Victoria’s Secret – and George was the nerdy doctor who was dubbed 007 for killing a patient on his first surgery. Many of the viewers cringed when the two got together, and subsequently found out that when they’re sober, they actually have no chemistry.


Laura and Urkel, Family Matters

Let’s all agree that Steve Urkel is the poster boy for nerd. He might be a genius, but with his thick glasses and suspenders, he’s far from being suave. He’s obsessed with his neighbor, Laura, who doesn’t return his love at first. When he creates his alter-ego Stefan Urquelle using his genes, Laura falls in love with the better-dressed and more graceful Stefan. Urkel then duplicates himself, creating separate versions of “Steve” and “Stefan”, who both propose marriage to Laura – but she ends up picking the nerdy Steve. So romantic!

Nancy and Jonathan, Stranger Things

Jonathan is the weird kid, introverted and antisocial, who lives with his single mother. Nancy is quite the opposite – a popular girl from a good home. But when his little brother and her best friend go missing, investigating things together leads to a romance between the two. She could probably do better, considering he sort of stalked her (taking pictures of her when she was undressed), but there’s undoubtedly a strong connection between the two.

Eric and Donna, That ’70s Show

If there’s one thing that Eric is into more than his beautiful red-headed neighbor, Donna, it’s Star Wars. Not only is he a major nerd, but he often loses when playing basketball or wrestling with Donna. But being a modern girl, she doesn’t mind that Eric is apparently weaker than she is, and the two commence in a romantic relationship. Even though Eric’s own friends keep hitting on Donna, she always stays true to Eric.

Tobias and Lindsay, Arrested Development

Tobias is a pretty weird guy, who left a successful career as a therapist to become a failed actor, and is also a “never-nude” (which is exactly what it sounds like). It’s unsure if Tobias is even attracted to women, but it doesn’t really matter since the two have zero chemistry – Lindsay only married Tobias to spite her parents. But Lindsay is just as bad, seeing that she’s hugely self-involved, irresponsible with money, and a neglecting mother to their daughter. All in all, this dysfunctional couple probably deserve each other.

Barry and Lainey, The Goldbergs

Barry and Lainey are the cutest couple, but they’re also pretty mismatched. We mean, don’t tell Barry about this – but he’s actually a nerd. Among his hobbies are rapping, hanging out with his “gang” (G-T-P!), and calling himself Big Tasty. Lainey is the beautiful, popular friend of Barry’s sister, Erica, who falls for the charms of this blissfully unaware geek. But as different as they are, their ’80s love story is both hilarious and sweet.

Anna and Bates, Downton Abbey

Anna and Mr. Bates were probably the most unexpected couple of the series, but their love tale was one of the most romantic ones. Anna is young, pretty, and intelligent, and Bates is older and disabled due to an injury, using a cane to walk. Even he was surprised when Anna took an interest in him, but she knew what she was doing – they turned out to be a great couple, who supported one another during difficult times.

Sam and Cindy, Freaks and Geeks

Sam was perhaps less socially inept than his friends, but he was still a geek. He spent a lot of time pining over pretty cheerleader Cindy, but it seemed like she was out of his league – she was popular and usually dated older students. But when she finally took an interest in Sam and they started dating, he realized just how shallow and possessive she was, and concluded he’d rather be alone than be with a girl like that. As it turned out, he was actually out of her league.

Marnie and Ray, Girls

Ray is a good guy, with a solid job as general manager of a coffee shop. But he doesn’t exactly seem like the perfect match for the gorgeous and ambitious Marnie – mostly because he gives off the vibes of an elderly man, constantly complaining about, well, everything. The connection between the two mostly based on their mutual loneliness, and their relationship continuously suffers from Marnie’s lack of real interest in Ray, and her all-around selfishness. Eventually, this is what causes Ray to turn the tables and leave Marnie.

Peter and Lois, Family Guy

Remember that time when Peter called Lois his reliable old plow horse at her birthday party (cue hilarious cutaway)? Peter may sometimes insult Lois, but it’s pretty obvious to everyone that she is way out of his league. For some reason, Lois sticks around Peter, even through all of his foolish shenanigans, which often lead to injuries, losing all of their money, or destroying their house. But considering that she can be pretty terrible herself at times, we’re saying these two are probably a good match.

Larry and Cheryl, Curb Your Enthusiasm

Larry is not exactly a looker, and while he’s extremely rich, famous, and hilarious – he’s also completely lacking in tactfulness and social etiquette of any kind. More often than not, speaking his mind causes a complete mess and generally pisses people off, so there’s no doubt that lovely young Cheryl could do a lot better. Although she eventually did leave him, the real reason behind it was Larry’s real-life divorce, which made him realize he needed to be divorced on the show as well.

Belle and Rumplestiltskin, Once Upon A Time

The couple might be based on Beauty and the Beast, but Rumple has done much terrible things than the cartoon version of the Beast. The beautiful, delicate Belle keeps putting her trust in the crocodile-like man, only to be constantly disappointed when he turns to his dark side again and again. But she keeps believing in him, and eventually manages to turn the Dark One into a somewhat decent man, not before she passes away of old age.


Leonard and Penny – The Big Bang Theory

From the moment bubbly Penny moved in next door, Leonard was pining for her. He thought he would never have a shot with the blonde bombshell – as her former boyfriends looked the exact opposite of him – and we all cheered when he turned out to be wrong. When they started dating, each of them put the other on a pedestal – Leonard thought he was too nerdy, while Penny thought she wasn’t smart enough for Leonard. But being out of each other’s leagues really makes them the perfect match.

Jay and Gloria, Modern Family

While his first marriage wasn’t very successful, Jay Pritchett’s second time around sure makes up for everything. Even he isn’t sure how he got Gloria to be his wife – she’s a stunning young Colombian bombshell, and he’s old enough to be her father (but ages aside, Sofia Vergara is pretty much in a league of her own). And while he’s rich, Gloria isn’t in it for the money, but loves Jay for all that he is.

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