The Time-Warp of Love: 13 ’90s Celebrity Couples and Where They Are in 2025

Before the carefully curated feeds of Instagram, there was the raw, untamed world of ’90s celebrity romance. This was an era of matching leather jackets, tiny sunglasses, grainy paparazzi shots, and gossip whispered across dial-up message boards. Back then, a couple on the cover of Teen People felt like a national event—a serialized TV show we followed without a subscription.

The pop culture coupledom of the ’90s was everything: a mix of wholesome heartthrobs, enigmatic “It” girls, and Hollywood wild cards. Some of these romances burned bright and faded fast, while others quietly drifted apart. Decades later, while you may not have thought about them, at the time, they were everything.

So, queue up that Alanis Morissette and Backstreet Boys playlist. Let’s hop in our mental time machine and revisit 13 totally iconic ’90s couplings—how they met, what they were like, and what life looks like for them in 2025.

Hollywood’s Golden Pairings

Matthew McConaughey & Sandra Bullock

Their connection began on the set of the 1996 movie A Time to Kill. Apparently, the on-screen sparks weren’t just acting. Matthew McConaughey and Sandra Bullock dated for a while, establishing a bond so strong that even after breaking up, they remained fiercely good friends. They’re the rare exes who still gush about one another in interviews. In 2025, McConaughey is happily married to Camila Alves (since 2012) and is a devoted father to their three children. Bullock remains one of the most beloved women in Hollywood, focusing her time on her two children and her enduring career.

Cameron Diaz & Matt Dillon

Before Cameron Diaz settled into her role as Hollywood’s ultimate cool-girl mom, she was linked to Matt Dillon in the late ’90s. They began dating in 1996 after circulating in the same Hollywood circles and eventually co-starred in the iconic comedy There’s Something About Mary. Dillon once called Diaz his “muse,” capturing that peak artsy-boy energy of the decade. The couple split in 1998. Diaz is now married to Benji Madden, with whom she has two children, and lives a happy, low-key family life. Dillon has been in a long-term relationship with Italian actress Roberta Mastromichele.

Music and TV Power Couples

Toni Braxton & Shemar Moore

In 1995, this was a pairing of a rising star and a certified superstar. Shemar Moore was a soap opera heartthrob, while Toni Braxton was a Grammy-winning powerhouse. Their brief romance gifted us some seriously glamorous red-carpet moments. Moore later joked that his ’90s claim to fame was being “the guy who dated Halle Berry and Toni Braxton”—a stellar résumé, indeed. Today, Moore is a proud father to his daughter, Frankie. Braxton continues to thrive in music and advocacy, and is a dedicated mother to her two sons.

Paula Abdul & John Stamos

A blink-and-you-miss-it romance, Paula Abdul and John Stamos were a thing in the early ’90s. They were the kind of couple that, when you saw them in a magazine, you thought, “Sure, that makes sense.” Though it didn’t last long, they have remained friendly, even sharing reunion selfies decades later. Stamos is now married to Caitlin McHugh and has a son. And Paula? She remains the same ageless, fabulous icon we remember.

Scott Wolf & Alyssa Milano

In 1993, Party of Five heartthrob Scott Wolf and Charmed star Alyssa Milano got engaged after only a year of dating—a quintessential young Hollywood romance. By 1994, they’d called it off with minimal drama. Milano is now married to talent agent David Bugliari and has two children. Wolf has three children from his marriage to Kelley Limp.

The Edgy and Unexpected

Edward Furlong & Natasha Lyonne

For fans of Terminator 2, Edward Furlong was forever John Connor. He dated Natasha Lyonne in the late ’90s after they met on the set of Detroit Rock City. They were rising stars with a palpable edge, embodying that peak alternative-’90s energy. While the romance was fleeting, Lyonne has since achieved massive success as a writer and star of Russian Doll and Poker Face. Furlong’s journey has, unfortunately, been more challenging since his ’90s stardom.

Kathy Griffin & Jack Black

Yes, this actually happened. Comedian Kathy Griffin and future superstar Jack Black went on a couple of dates in the ’90s. Griffin still hilariously recounts the experience, particularly the time she discovered his “shower towel” was actually his bath mat. It wasn’t a grand love story, but it’s a brilliant anecdote. Black is now happily married with children, and Griffin continues to deliver her signature unfiltered, hilarious commentary.

Jewel & Sean Penn

One of the most unexpected couplings of the decade. In 1995, Sean Penn saw Jewel perform on Late Night with Conan O’Brien, got her number, and they dated for a short while. Jewel wrote in her memoir that she found the intense actor “charming and witty.” Today, she continues to tour and create music, while Penn remains a prominent, headline-making figure in acting and directing.

Teen Dreams and Breakout Stars

Scott Speedman & Keri Russell

Felicity fans were treated to a real-life romance mirroring the hit show. Scott Speedman and Keri Russell dated off-screen while portraying the iconic college couple, Ben and Felicity. It was life imitating art, even if the romance didn’t last. Both have moved on but remain good friends. Speedman is a father, and Russell is in a long-term, adorable relationship with fellow actor Matthew Rhys.

Andrew Keegan & LeAnn Rimes

This relationship started like a teen movie script. A 15-year-old LeAnn Rimes spotted Andrew Keegan—the ultimate ’90s teen idol—in a magazine, said he was cute, and her manager literally called him up. They dated for about three years. Rimes is now married to Eddie Cibrian and is a stepmother to his two sons. Keegan is a father to his daughter, Aiya Rose.

Drew Barrymore & Luke Wilson

The ultimate laid-back couple of the late ’90s. Drew Barrymore and Luke Wilson were defined by their casual, cool vibe. Barrymore has referred to their relationship as an open one, stating they were just “young, having fun, and not taking it too seriously.” They split but have stayed friendly. Barrymore now hosts her own popular talk show and is raising two daughters, while Wilson continues to work steadily across film and television.

Owen Wilson & Sheryl Crow

Owen Wilson and Sheryl Crow met on the set of The Minus Man in 1999 and dated for approximately two years. Crow even referred to Wilson as “the love of my life” in interviews at the time. Today, Crow is a mother of two and still actively performing, and Wilson’s career is as prolific as ever.

Will Friedle & Jennifer Love Hewitt

In a flash of pure ’90s teen star magic, Boy Meets World star Will Friedle brought Jennifer Love Hewitt as his date to the 1997 premiere of I Know What You Did Last Summer. She later appeared on his show as his on-screen love interest. The relationship was short-lived, but the memory lives on. Hewitt is now married with three children, and Friedle has been married since 2016.

These couples, in their matching denim and tiny shades, weren’t just dating—they were defining a generation’s view of romance. They were the heart of pop culture before social media took over. Which ’90s celebrity relationship do you think was the most iconic?