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.
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.
