The world will always remember Bennifer, Brangelina, TomKat and Kimye, but other star couplings have been slowly forgotten over the years. Wonderwall.com rounded up 28 celeb couples of the ’90s that were kind of a big deal at the time but that no one seems to remember now, starting with this A-list actress and ’90s sitcom star… There were a lot of benefits to starring on “Friends” — like the ability to get up close and personal with bona fide movie star Julia Roberts, which is exactly what Matthew Perry did after she appeared on a 1996 episode of the NBC sitcom. In early 2021, “Friends” executive producer Kevin Bright revealed that Matthew actually reached out directly to Julia to ask her to appear on the show: “She wrote back to him, ‘Write me a paper on quantum physics and I’ll do it.’ My understanding is that Matthew went away and wrote a paper and faxed it to her the next day,” he told The Hollywood Reporter. Added staff writer Alexa Junge of the connection between the funnyman and the iconic actress, “They may have met before the episode, but she was interested in him from afar because he’s so charming. There was a lot of flirting over faxing. She was giving him these questionnaires like, ‘Why should I go out with you?’ And everyone in the writers room helped him explain to her why. He could do pretty well without us, but there was no question we were on Team Matthew and trying to make it happen for him.” The duo were spotted together on several dates that year, but a source told People magazine at the time that things were just “casual” between them. Now keep reading for more forgotten ’90s couples…
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Long before he had high-profile relationships with Alanis Morissette, Scarlett Johansson and Blake Lively, Ryan Reynolds dated Kristen Johnson. The rising actor and the “3rd Rock from the Sun” funnywoman reportedly dated for a few months between 1999 and early 2000.
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Chris O’Donnell started seeing his wife, Caroline Fentress, when he was in college, so it often feels like they’ve been together forever. But that’s not the case! The “NCIS: Los Angeles” star and Reese Witherspoon were just babies when they dated for a few months back in 1993 — he was in his early 20s and she was still a teenager. (Chris met his future spouse right after he and Reese parted ways.)
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David Arquette was an up-and-coming actor and Alyssa Milano was a child star nearing the end of her run on “Who’s The Boss?” when the two hooked up during the early ’90s. She went on to marry Dave Bugliari, while he famously romanced Courteney Cox. They still have (platonic) love for each other, though: In 2019, the “Scream” actor tweeted that he was “so proud” of his former love and her activism work in Georgia.
Leonardo DiCaprio and Liv Tyler reportedly dated after she shot scenes for Woody Allen’s 1996 film “Everyone Says I Love You,” which also featured actor Lukas Haas, Leo’s BFF. Her scenes were ultimately cut from the film, but her Hollywood hookup probably made those days of work well worth the wasted effort!
While there aren’t many details out there about the romance between Claire Danes and Ben Lee, we do know that their meet-cute came courtesy of Winona Ryder. The “My So-Called Life” actress and the Australian music star dated from 1997 to 2003. The demise of their relationship was reportedly a result of Claire’s affair with her “Stage Beauty” co-star Billy Crudup, who at the time was expecting a child with longtime girlfriend Mary-Louise Parker. Yikes.
Seal sure has a way with supermodels! Before he wed Heidi Klum, the singer romanced Tyra Banks. They were photographed together at several big Hollywood events back in 1996.
Christine Taylor and Neil Patrick Harris dated back in 1997. “She’s like, the coolest, nicest chick ever,” the actor told radio host Howard Stern in 2008 of his relationship with Ben Stiller’s future wife. “She’s an absolute catch, and I thought, ‘If I’m not going to feel the super-sparks with her, than it probably means that I’m gay.'” Indeed!
Ashton Kutcher dated a pre-fame January Jones from 1998 to 2001. (She didn’t make her acting debut until 1999.) The “Mad Men” star opened up about their relationship — which kicked off the same year that his series “That ’70s Show” debuted — during a 2009 interview with GQ: “The guy I was dating when I first got to L.A. was not supportive of my acting,” she said. “He was like, ‘I don’t think you’re going to be good at this.'” Ouch!
Courteney Cox and Michael Keaton were an item for a whopping five and a half years before they called it quits in 1994, the same year that her hit show “Friends” debuted. The duo were extremely private during their time together, which is why we often forget they were ever a thing.
Speaking of forgotten “Friends” romances… Jennifer Aniston and Tate Donovan started dating in 1995 and called it quits in 1998. At the time, there were rumors they’d even quietly gotten engaged. Tate guest starred on “Friends” for six episodes as Joshua, a love interest for Jen’s Rachel Green. “The people that know that we dated think that we met on ‘Friends,'” he told Us Weekly years later. “But in fact we had dated for two years before then, and it was over by the time we were on ‘Friends’ together.” He further admitted that though they were professional while working together, the experience was “really painful and tough” and that he was “sort of dying inside.”
These days, David Spade’s list of romantic conquests is practically legendary, and it all started with Kristy Swanson, his first Hollywood hookup. The “8 Heads in a Duffel Bag” co-stars reportedly dated for about a year between 1996 and 1997.
Drew Barrymore and Luke Wilson began dating in 1996 and split in 1999, not long after co-starring in the dark comedy “Home Fries.” She later told People magazine of their romance, “From the moment I saw him, I realized he was the most incredible person I’d ever been so fortunate to meet.” But Luke isn’t Drew’s only forgotten romance…
Drew Barrymore and Edward Norton reportedly dated around the time that they shot the 1996 Woody Allen film “Everyone Says I Love You.” She went on to date Luke Wilson but reunited with Ed in 1999 after her relationship with the “Old School” actor came to an end. (Drew attended the 1999 Academy Awards on Ed’s arm.) The A-list actress has been all over the dating map, romancing everyone from Tom Green and Corey Feldman to Justin Long and Will Kopelman, which is probably why her relationship with the Oscar nominee failed to make a lasting impression.
Paula Abdul and Emilio Estevez didn’t just date — they were married! The duo tied the knot in 1992 but split just two years later. She blamed the breakup on her desire to have children while Emilio, who already had two kids from a previous relationship, didn’t want to become a father again.
Ted Danson was still married to producer Casey Coates when sparks flew between him and Whoopi Goldberg on the set of 1993’s “Made in America.” Their whirlwind romance was big tabloid fodder, with the most memorable moment coming when the “Cheers” star decided to perform in blackface at a Friars Club roast for the funnywoman. That epitomized the bad idea that was this relationship, and by the end of 1993, it was over, with Whoopi moving on to date her orthodontist.
Uma Thurman was just 20 when she wed 32-year-old Gary Oldman in 1990. (It was his second marriage and her first.) They parted ways after just two years of marriage, and she went on to enjoy a headline-making marriage with Ethan Hawke. Moving on to an even more dramatic relationship is certainly one way to get the public to forget about the first! (Gary, by the way, has tied the knot three more times since then.)
Madonna is always reinventing herself, and back in the early ’90s, she briefly reinvented herself as Vanilla Ice’s paramour. But like slap bracelets and Beanie Babies, all good ’90s fads eventually came to an end, including Madonna and her Ice, Ice Baby. Their relationship thawed when the pop star released her “Sex” book, which the rapper told the now-defunct News of the World he was “hurt to be an unwitting part of.”
Matthew McConaughey and Sandra Bullock — co-stars in the 1996 flick “A Time to Kill” — were very quiet about their romance, with the actress claiming that they were friends, but not necessarily “just” friends. Their romance might not have worked out, but they’ve definitely maintained a friendship over the years.
During the late ’90s and early aughts, Sheryl Crow and Owen Wilson made sweet music together. Well, she made the music and he probably made her laugh once in a while. The actor and the Grammy winner dated for about two years after meeting on the set of the 1999 movie “The Minus Man.”
Cameron Diaz and Matt Dillon dated for three years before they split in 1998 after co-starring in “There’s Something About Mary.” According to reports, the actor’s desire to settle down with the blonde beauty, who wasn’t ready at the time, was reportedly to blame.
During the height of her fame as a teen, “I Know What You Did Last Summer” and “Can’t Hardly Wait” star Jennifer Love Hewitt romanced “TRL” host Carson Daly. The duo got together in 1998 though ultimately called it quits a year later. Carson reportedly found out about the demise of their relationship through the actress’s publicist — but not before getting her name tattooed on his ankle! The former MTV host told People magazine that he “woke up to [radio host] Howard Stern telling me my relationship with [Jen] was over.” Ouch.
Danielle Fishel and Lance Bass dated from 1999 to 2000 — they even went to prom together! Clearly there are no hard feelings between the former teen lovers, who reunited on the red carpet at a book release party in 2006 — the same year the boybander publicly revealed he’s gay.
Matt Damon and Minnie Driver had undeniable chemistry in “Good Will Hunting,” so it’s no surprise that in real life, they were an item for seven months back in 1997. So why don’t we remember their romance? It’s often eclipsed by what came next for the A-list actor: He hooked up with Winona Ryder at a New Year’s Eve party and didn’t bother to tell Minnie that they were through until he appeared on “The Oprah Winfrey Show” and publicly announced that they’d parted ways, which Minnie later called “fantastically inappropriate.” He and Winona were an item for the next three years.
As for the “other” woman… Matt Damon and Winona Ryder met in December 1997 thanks to none other than Gwyneth Paltrow, who was dating Matt’s bestie, Ben Affleck, at the time. Matt and Winona were a couple for three years before ending their relationship in 2000. The “Good Will Hunting” star would go on to date Penelope Cruz, his co-star in the 2000 romantic Western “All the Pretty Horses.”
Speaking of Ben Affleck and Gwyneth Paltrow… Before the “Good Will Hunting” star romanced two famous Jennifers, he was in a relationship with this blonde beauty. The stars dated from 1997 to 2000. According to the actress, their split was due to their differing values. “Ben makes life tough for himself,” Gwyneth told Diane Sawyer in 2003. “He’s got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out.”
Of course, Goop also spent time with another ’90s hunk… The romance between Brad Pitt and Gwyneth Paltrow, who met making the psychological thriller “Seven” in 1994, took off like wildfire. Believe it or not, while accepting his Golden Globe for best supporting actor for his work in “12 Monkeys” in 1996, Brad thanked Gwyneth and even referred to her as “the love my life.” By the end of the year, they’d gotten engaged. But it wasn’t meant to be: The duo — who rocked matching haircuts in 1997 — ended their engagement six months later. Oh, the ’90s!
While Johnny Depp’s romance with Winona Ryder has gone down in pop culture history as one of Hollywood’s most memorable pairings of the ’90s, this one is sometimes forgotten. Johnny dated British model Kate Moss throughout the ’90s and together, they epitomized the era. The couple met in 1994 at New York City’s Cafe Tabac and were an item until 1998 – they were even reportedly engaged at one point during their tumultuous relationship. (Unfortunately, Johnny’s romantic life doesn’t seem to have gotten any easier since then.)
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