The ’90s and early 2000s were a beautiful, beautiful time in terms of clothing, hairstyles and pop culture trends. Some of the best teen movies were filmed in these decades, and we had some of our fiercest crushes while watching these films — who could forget how Freddie Prinze Jr.’s character in She’s All That made us feel when he realized he’d liked Laney Boggs all along, or how Heath Ledger’s character in 10 Things I Hate About You was the only one who truly understood Julia Stiles? Our hearts still beat for the men of the ’90s and early 2000s, and here are just a few of the boyfriends we’d still date today in a second.


1. Patrick (Heath Ledger) from 10 Things I Hate About You. First things first: Heath. Ledger. This movie is great, and Heath Ledger was great in it. His character, Patrick, seems to have actual integrity — he doesn’t want to be a part of the scheme that is the central plot to the movie, and while he eventually gives in, he falls in love with Kat in the process (aww!). He also has a little bit of an edge, while managing to still get emotional when Kat reads the poem the movie is named for. We have a soft spot for men who can show their feelings in public without being worried it’ll tarnish their masculinity. He’s a Grade-A ’90s boyfriend, if you ask us.

2. Cameron (Joseph Gordon-Levitt) from 10 Things I Hate About You. We honestly can’t talk about 10 Things I Hate About You without also mentioning JGL. He was SERIOUSLY under-appreciated in this role. While he might’ve gone about it in the wrong way, all he ever wanted to do was take Bianca out — and we think that kind of take-no-prisoners love is pretty sweet, especially at such a young age.

Freddie Prinze Teen

3. Zack (Freddie Prinze Jr.) from She’s All That. Ahh, another teen movie about a girl, a boy, a date and a bet. There was quite a theme happening around this time! Zack Siler was the jock with a heart — he somehow got himself roped into one of these ugly duckling prom bets, but he still managed to be lovable in our eyes, and in Laney Boggs’ eyes, too. They made a cute couple in the end (though we actually preferred her in her falafel hat…).


4. Michael (Robert Schwartzman) from The Princess Diaries. Michael was TRUE BLUE. He always liked Mia — before she was a princess, before she had her makeover, before everything. He stuck around during all the weird stuff — even during the time period where she let her straightener go to her head and thought she was too good for him. The two shared their first kiss at the end of the movie, and ALL of us got butterflies.


5. Preston (Ethan Embry) from Can’t Hardly Wait. Preston Meyers was David to Mike Dexter’s party Goliath in Can’t Hardly Wait. He had been in love with Amanda Beckett, who had been dating Mike, for a long time, and was trying to get the courage to tell her — a task that seemed nearly impossible, given that Mike and Amanda were a match made in high school heaven. However, over the course of the night, and tiny vignettes filmed around the party, it’s made clear that there is life beyond high school, and Preston might just be the right choice for girls (and women) who know that. Sigh.


6. Derek (Sean Patrick Thomas) from Save the Last Dance. Oh, Derek. Derek came in and helped Sara when she needed it most — when she was away from home, feeling clueless, and in need of a few new moves. He showed her how to love dance again and supported her studies. He was endlessly patient with her when she didn’t understand certain dynamics at play between his friends and family, and he helped her do the work to understand what it means to be a good partner. Plus, he’d be a great partner to take out on the dance floor at a wedding — just saying.

7. Jack (Leonardo DiCaprio) from Titanic. Our hearts have been going on about Jack since 1997. Just LOOK at him. TBH, we’re kind of wondering if the fact that he’s down there in the ocean is partially responsible for melting all those icebergs faster. Seriously though, he’d be a wonderful boyfriend, if he was a real person, and in today’s world, and y’know, not dead. He loves fiercely, and while he doesn’t exactly have his finances in order, he’s super scrappy and knows how to think on his feet. We’d trust him with our lives.


8. Josh (Paul Rudd) from Clueless. Okay, so even if his feelings for Cher were a little bit strange, we still love Josh. He is (mostly) a good older stepbrother, and he has a lot of wisdom in that head of his. He was always kind to her, and never really stooped down to gossip or pettiness the way most other people did in Clueless. He also has that “I don’t care what I look like” thing going for him, even though he usually looks pretty good. Also, can we point out that Paul Rudd STILL looks exactly the same? Good genes are nothing to sneeze at.

9. Austin (Chad Michael Murray) from A Cinderella Story. It would almost feel wrong to talk about the early 2000s without talking about Chad Michael Murray — but have no fear, here he is. And in an adaptation of a popular Disney story, no less! In this movie, he plays Austin, a popular jock who still can’t find happiness (aww!). He starts writing Sam (played by Hillary Duff) and a modern version of Cinderella plays out right before our eyes. In the end, they kiss in the rain and go to Princeton together, as most modern-day teen couples do.

So there you have it! Those are our fave boys from the ’90s and early aughts; who are some of yours? Tweet us at @BritandCo!

(Photos via Touchstone Pictures, Miramax Films, Buena Vista Pictures, Columbia, Paramount Pictures, 20th Century Fox, Warner Bros. Pictures)