A Short History of the Teen Rom-Com's Most Beloved Boyfriends

By Maria Sherman | September 7, 2018 | 6:30pm

Entertainment Movies

Long before Noah Centineo made our palms sweat as the wholesome hunk Peter Kavinsky in Netflix’s To All the Boys I’ve Loved Before, other hotties were doing the exact same thing. Call it the curse of the sweltering high school heartthrob, but (all of my) boyfriends in teen rom-coms have been bringing it—or at least, they did, when I was but a horny adolescent soon to become a horny adult—for a few decades now.

While romantic comedies have a long and storied legacy—from 1957’s An Affair to Remember to 1993’s Sleepless in Seattle and 2018’s Set It Up (or whatever)—I’m thinking more specifically about the teen-centric flicks; the delightful heteronormative nonsense that promises viewers fairytale love and teenage boys with surprising levels of emotional maturity. I adore the fantasy.

Jake Ryan in Sixteen Candles (1984)

Teen rom-coms didn’t exist until John Hughes started making them in the ’80s, or so it should be recognized (call me to confirm your canon). It was a challenge to pick just one of Hughes’s flicks for the sake of this blog, but it’s without a doubt Jake Ryan, played by Michael Schoeffling in 1984’s Sixteen Candles. Jake Ryan messed everyone up in the most romantic way—not only was he hot, sensitive, and bit his bottom lip like nobody’s business, but he made Molly Ringwald feel like the only damn girl in the world, which is good because no one remembered that bitch’s birthday. As the Covey sisters pointed out, Sixteen Candles had some ugly racist stereotypes, but Jake Ryan.*

*As an adult rewatching the film, it came to my attention that the whole party scene where Ryan lets his friend drive his very drunk girlfriend home was extremely fucked up (as Molly Ringwald noted in an essay this year) and he’s not a true hunk… he’s more like a sheep in hunk’s clothing?

Teen Rom-Com Boyfriend Rating: 5/10

Josh Lucas in Clueless (1995)

In a truly astonishingly and brilliant marketing ploy, Josh Lucas (Paul Rudd) isn’t even featured in the original Clueless trailer, so watching this movie for the first time, without context, must have been nuts. It’s kinda like how Disney kept all the princess iconography out of the original promo for Frozen because they were like “little boys won’t like this sisterhood shit” and they were so wrong?

Anyway, who would have thought the seemingly vapid Cher Horowitz (Alicia Silverstone) would fall for the goofy, hard-working lawyer boy Josh? I certainly did not, because their age difference is really gross. But did I still have a big lady boner for young Paul Rudd? You better believe it.

Teen Rom-Com Boyfriend Rating: 6/10

Patrick Verona in 10 Things I Hate About You (1999)

Karaoke, long curly locks on white boys, huge romantic gestures and the Frankie Valli and the Four Seasons hit “Can’t Take My Eyes Off of You” were all wack until Heath Ledger came long, swept us all off our feet and somehow convinced the nerds in the marching band to participate. I assume this is how promposals became a thing. Thanks, Shakespeare.

This is the first time you wanted to be Julia Stiles, even when Ledger fake dates her in the beginning.

Teen Rom-Com Boyfriend Rating: 6/10

Michael Moscovitz in The Princess Diaries (2001)

At its heart, The Princess Diaries is more than a teen rom-com. It’s a tale of a young woman coming to terms with herself and her legacy, but also becoming confident and a, well, motherfucking princess. There’s also romance, of course, and she falls for musician/mechanic Michael Moscovitz, played by Robert Schwartzman of the band Rooney. She literally falls for a pair of eyebrows and “the guy from that band” trope we all continue to suffocate in. The Princess Diaries also gives us the greatest apology ever—a pizza with M&M toppings that spell out “SORRY.”

BONUS: Please don’t forget the goosebumps-inducing dialogue of Mike asking “Why me?” and Anne Hathway responding, “Because you saw me when I was invisible.” Zamn.

Teen Rom-Com Boyfriend Rating: 8/10

Ian Wallace in What A Girl Wants (2003)

This movie made the bar for good teen rom-com boyfriends enter the Earth’s orbit because now not only did we pine for musicians, those hard-working, kind, hot-as-hell sweeties, but they needed to be ENGLISH, TOO! What the fuck?

Teen Rom-Com Boyfriend Rating: 7/10

“Woodchuck” Todd in Easy A (2010)

I’m not totally sure the argument can be made for Easy A as a tried and true rom-com (I think The Scarlet Letter reboot is a bit more of a hybrid, but there are already two loose literary adaptations on the list, so let’s go with it) but it does two things really well: star Emma Stone, the Molly Ringwald of the early 2010s, and end in romance with Penn Badgley of Gossip Girl fame, a hot-nerd-but-not-actually-a-nerd-and-probably-a-bad-guy of the same period. Either way, I wanted to smash. Same goes for another Emma Stone rom-com boyfriend, Tyson Ritter in the 2008 film The House Bunny. And all similar movies. She did a bunch.

Teen Rom-Com Boyfriend Rating: 6/10

Peter Kavinsky and Jamey To All the Boys I Love Before / Sierra Burgess Is a Loser (2018)

And then there was Noah Centineo, the ultimate teen rom-com boyfriend. He is hunky as hell, kind, sensitive, vulnerable, athletic, smart, romantic… shall I go on? I’ll stop short of “perfect” because that title is reserved for Harry Styles alone, but also because Centineo’s characters do some major emotional growth in both movies. As a devoted rom-com viewer, I stan a dude who learns from his past and present behaviors to become a mature, wonderful person. Also, he’s just hot and thoughtful, and isn’t that all we want in a rom-com boyfriend at the end of the day?

Teen Rom-Com Boyfriend Rating: 27/10