Before celebrity couples were “Instagram official,” they were splashed across Teen People covers, immortalized in grainy paparazzi shots, and whispered about on dial-up-era message boards. The ’90s were peak pop culture coupledom — an era when red carpet dates meant matching leather jackets, tiny sunglasses, and absolutely no PR team-approved captions.
Some of these romances burned bright and fizzled fast; others quietly drifted apart without any drama. And while you might not have thought about them in decades, at the time they were everything — the heartthrobs, the “It” girls, and the Hollywood wild cards whose love lives we followed like a serialized TV show.
So let’s hop in our mental time machine, cue up some Alanis Morissette and Backstreet Boys, and revisit 13 totally ’90s couples — how they met, what they were like together, and where they are now in 2025.
Matthew McConaughey & Sandra Bullock
Matthew McConaughey and Sandra Bullock met on the set of A Time to Kill in 1996, and apparently the sparks on screen weren’t acting. They dated for a while but stayed friends after breaking up — the kind of friends who still gush about each other in interviews. McConaughey’s been married to Camila Alves since 2012 and has three kids, while Bullock is a devoted mom to her two children and still one of the most beloved women in Hollywood.
Cameron Diaz & Matt Dillon
Before Cameron Diaz was Hollywood’s ultimate cool-girl mom, she was dating Matt Dillon in the late ’90s. They met while working in the same Hollywood circles and started dating in 1996, eventually co-starring in There’s Something About Mary. He once called her his “muse,” which is either incredibly romantic or peak artsy-boy energy. They split in 1998, and both moved on — Cameron married Benji Madden, has two kids, and lives a low-key family life, while Matt’s been with Italian actress Roberta Mastromichele for years.
Toni Braxton & Shemar Moore
In 1995, Shemar Moore was a rising soap star and Toni Braxton was already a Grammy-winning powerhouse. They dated briefly, giving us some seriously glamorous red carpet moments. Shemar later joked that he was “the guy who dated Halle Berry and Toni Braxton” in the ’90s — not a bad résumé. Now Shemar’s a proud dad to his daughter Frankie, and Toni is busy with music, advocacy, and raising her two sons.
@stayforthelove Toni Braxton & Shemar Moore in the 1994 music video for the song “How Many Ways” #tonibraxton #shemarmoore #musicvideo #90sfine #90smen #90saesthetic #edit #fypage #blackhollywood #foryoupage
Paula Abdul & John Stamos
Paula Abdul and John Stamos were a thing in the early ’90s — blink and you might’ve missed it. They were the kind of couple you saw in a magazine and thought, “Yeah, that makes sense.” It didn’t last long, but they’ve stayed friendly, even posting reunion selfies decades later. These days, Stamos is married to Caitlin McHugh and has a son, and Paula… well, she’s still Paula, ageless and fabulous.
Scott Wolf & Alyssa Milano
Back in 1993, Charmed star Alyssa Milano and Party of Five heartthrob Scott Wolf got engaged after dating for just a year. It was very “young Hollywood romance,” but by 1994, they’d called it off. No drama, no messy tabloid headlines — just two ’90s icons going their separate ways. Now Alyssa’s married to talent agent David Bugliari with two kids, and Scott has three kids from his marriage to Kelley Limp.
Edward Furlong & Natasha Lyonne
Edward Furlong — forever John Connor to Terminator 2 fans — dated Natasha Lyonne in the late ’90s after meeting on the set of Detroit Rock City. They were both rising stars with a bit of an edge, and while the romance didn’t last, it was peak alternative-’90s energy. Natasha has gone on to huge success with Russian Doll and Poker Face, and Edward… well, let’s just say his post-’90s journey has been a lot more complicated.
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Scott Speedman & Keri Russell
Fans of Felicity will remember Scott Speedman and Keri Russell’s on-screen romance as Ben and Felicity — but they also dated in real life. It was the perfect mix of life imitating art, though it didn’t last forever. They’ve both moved on romantically but have stayed good friends. Scott’s a dad now, and Keri’s in a long-term relationship with Matthew Rhys (and yes, they’re as cute together as you’d imagine).
Kathy Griffin & Jack Black
Yes, this actually happened. Comedian Kathy Griffin and Jack Black went out a couple of times in the ’90s, and she still teases him about it — especially the time she discovered his “shower towel” was actually his bath mat. It wasn’t a big love story, but it’s a great anecdote. Now Jack’s happily married with kids, and Kathy’s still delivering unfiltered, hilarious commentary on everything.
Andrew Keegan & LeAnn Rimes
Andrew Keegan and LeAnn Rimes’ relationship started like a teen movie — literally. LeAnn spotted him in a magazine when she was 15, said he was cute, and her manager called him. They dated for about three years, which is basically a lifetime in teen romance years. Now LeAnn’s married to Eddie Cibrian and is a stepmom to his two sons, and Andrew is a dad to daughter Aiya Rose.
Drew Barrymore & Luke Wilson
Drew Barrymore and Luke Wilson were the ultimate laid-back couple of the late ’90s. She’s said it was an open relationship, and that they were just “young, having fun, and not taking it too seriously.” They split after a few years but stayed friendly. Drew now hosts her own talk show and is raising two daughters, while Luke’s still working steadily in Hollywood.
Jewel & Sean Penn
In 1995, Sean Penn saw Jewel perform on Late Night with Conan O’Brien, got her number, and the two ended up dating for a short while. It’s the kind of unexpected pairing you forget happened until someone shows you a throwback photo. Their romance didn’t last long, but Jewel wrote about finding him “charming and witty” in her memoir. These days, she’s still touring and making music, and Penn’s still acting (and still making headlines).
Owen Wilson & Sheryl Crow
Owen Wilson and Sheryl Crow met on the set of The Minus Man in 1999 and dated for about two years. She even referred to him as “the love of my life” in interviews back then. They went their separate ways, and now Sheryl’s a mom of two and still performing, while Owen’s career is as strong as ever.
Will Friedle & Jennifer Love Hewitt
In 1997, Boy Meets World star Will Friedle brought Jennifer Love Hewitt as his date to the I Know What You Did Last Summer premiere. She later appeared on his show as his love interest, and they shared a makeout scene so intense that Friedle says it’s “uncomfortable” to watch now. It was short-lived, but pure ’90s teen star magic. Hewitt is now married with three kids, and Friedle’s been married since 2016.
