Who Would You Date In The Battle Of The 90s TV Boyfriends?

I’m a fierce TV watcher. I take it VERY seriously and was a hard-core binger wayyy before the phrase even became a hot trending topic. I’m also a lover of the ’90s. I fall in love with characters — OK, lots of times as if they were real people! — and my teen years were spent in a haze of TV’s best boyfriends. Thanks to the teen drama boom spearheaded by the WB, there seemed to be a guy for everyone.

So let’s take a little trip down memory lane, shall we? Who would win in a Battle of the ’90s TV Boyfriends? Here are 10 top contenders, known for everything from their keen sense of style to their brooding nature…

Related-ish: What Your Favorite ’90s Female TV Character Says About You


Dawson Leery, Dawson’s Creek

tv boyfriends Who Would You Date In The Battle Of The 90s TV Boyfriends?

Oh, the countless weeknights I spent getting lost in those deep philosophical monologues. Dawson was smart and pensive, unlike practically every teenage boy I knew. The conversations we could have…if only he were real.

Date-night hot spot: A museum or an art gallery opening — perfect for quiet conversation and a high dose of culture!

Chandler Bing, Friends

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In one of my teenage journal entries, I literally wrote that my ideal guy needed to have a Chandler Bing sense of humor. He was funny and all kinds of self-deprecating in the sexiest way. Plus, he wasn’t as serious and dull as a certain other ‘Friend’ — looking at you, Ross Gellar!

Date-night hot spot: Some New York City comedy club, where you’d laugh the night away, and then grab a slice of pizza while you walk and talk — and probably laugh even more!

Angel, Buffy The Vampire Slayer

tv boyfriends Who Would You Date In The Battle Of The 90s TV Boyfriends?

Not to be confused with his alter ego, Angelus, because no one could put up with that level of evil. Angel, on the other hand, was the perfect combo of brooding, stylish, deeply introspective superhero. Just don’t take him home to meet your parents — I mean, he was 200+ years old. But he could probably help you with your history homework because, you know, he probably lived through it.

Date-night hot spot: A dimly lit restaurant at night, obviously, for some meaningful and soul-searching conversation. That, or a stroll through the cemetery.

Uncle Jesse, Full House

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I watched every episode of Full House and was jealous of Becky the whole time! Jesse was that guy you weren’t sure you should get involved with — sweet, but just a little wild. Remember that motorcycle episode? Still, his love of Elvis made him endearing.

Date-night hot spot: Vegas. An Elvis show. And if the date goes really well, maybe a quick stop at a wedding chapel.

Jordan Catalano, My So-Called Life

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Oh, Jordan — so mysterious and standoffish. He must have had the weight of the world on his shoulders, but honestly, that’s what made him more intriguing. And that stare!

Date-night hot spot: He’d probably think the idea of “dating” is giving in to the man, but I’m sure he’d be down for “hanging out” or whatever that means. He just “doesn’t do labels.”

Cory Matthews, Boy Meets World

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He was every teenage girl’s dream. The kind of sensitive guy who’d follow you around with those puppy dog eyes. Yes, that Topanga was one lucky lady.

Date-night hot spot: Can’t go wrong with the classic dinner and a movie. Just don’t stay out too late since you’ll probably need a ride from your parents!

Zack Morris, Saved By The Bell

tv boyfriends Who Would You Date In The Battle Of The 90s TV Boyfriends?

Zack (aka, Preppy) was the ultimate California Dream — a blonde-haired, semi-slacker who was always scheming, but deep down, had a heart of gold. And when he brought the Bayside prom to Kelly’s house?? Totally swoon-worthy!

Date-night hot spot: The Max, of course! Hey, maybe a dance contest will even break out!

Will Smith, The Fresh Prince of Bel-Air

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Will knew what it felt like not fitting in, but he never let that dampen his spirit. He was always the life of the party, and that was refreshing.

Date-night hot spot: He’d probably know where ALL the happening parties were and could get you in! Private dance lessons included.

Steve Urkel, Family Matters

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You can’t talk about ’90s TV without mentioning Steve Urkel. I never understood why the Winslow family was so mean to him. Sure, he could be a bit annoying at times, but his sweet sincerity and devotion to Laura was adorable. He was a hip geek long before the guys from The Big Bang Theory.

Date-night hot spot: A local polka festival, during which time he’ll give you the history of polka, his favorite polka songs and maybe even get up on stage and dedicate a tune to you. You know, since he actually brought his accordion with him on the date.

Brandon Walsh, Beverly Hills 90210

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Brandon was every parent’s dream — a good, clean-cut boy from Minnesota who has yet to be corrupted by that California sun.

Date-night hot spot: If it’s his night off from the Peach Pit, perhaps he’d plan a romantic picnic on the beach, complete with a ’90s slow jam in the background!

So, who grabs the #1 spot? It’s a tough call, I know, but someone has to decide!

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