Talk about a blast from the past!
Though it has been more than two decades since these couples held hands on a red carpet or cuddled up on a vintage couch, we dug through the archives and pulled out our favorite photos of these so very nostalgic pairings.
From Toni Braxton and Shemar Moore’s sexy award show looks to Sandra Bullock and Matthew McConaughey’s adorable stares, take a look back at these couples you might not have thought about this millennium.
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In addition to starring in 1998’s There’s Something About Mary together, Dillon and Diaz also dated in the 1990s after meeting years prior on nearby film sets. She told Britain’s Guardian in 1997, “I love him incredibly.”
Years after their relationship ended, Dillon told Parade, per CBS News, that Diaz was a “muse.”
“It’s a very powerful thing when you feel that way about somebody,” he said of falling in love. “Cameron was a muse for me. I hadn’t been in any deep emotional relationships.”
Diaz now shares two children with husband Benji Madden.
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Stamos and Abdul, seen here in the early ’90s, dated for a time and have kept up a friendship over the years. In 2015, Abdul shared a throwback photo of the pair alongside a reunion shot that Stamos posted on his own Instagram page as well.
“Cold Hearted Snake and America’s sweetheart,” Stamos wrote. “Together again and it feels so good.”
Stamos married his wife Caitlin McHugh Stamos in 2018 and they welcomed their son Billy that same year.
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Wolf and Milano dated briefly in the early 1990s and were even engaged for six months before the relationship ended amicably in 1994.
The Charmed alumna is now married to talent agent David Bugliari, with whom she has two children, and Wolf shares three children with his estranged wife Kelley Wolf.
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The two Oscar-winning actors dated after first meeting on the set of their 1996 film A Time To Kill.
“We dated for a while after A Time to Kill, and we’re still friends,” he told Playboy in 2016. “She and I have another version of our relationship to put on film, and we’re looking for something. She’s not a little girl. She’s a woman. She could run a country.”
McConaughey now shares three kids with his wife Camila Alves McConaughey while Bullock is mom to son Louis and daughter Laila. The two don’t just share a dating history; they also both have deep ties to Austin, Tex.
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The S.W.A.T. star was one-half of a few iconic ’90s couples — including this memorable pairing with the Grammy winner in 1995.
While speaking with PEOPLE about his “pretty good entrance into Hollywood,” he explained how he became known as “the guy who dated Halle Berry [in 1997] and Toni Braxton [in 1995].”
Years later, Moore welcomed his first daughter Frankie with now ex-girlfriend Jesiree Dizon and Braxton welcomed two children with her ex-husband Keri Lewis.
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While the two played love interests onscreen as Felicity and Ben on Felicity from 1998 to 2002 they also dated off-screen for a time. (Did that make it awkward when Felicity decided to pursue Noel?)
While they both are now in long term relationships with other people, the two remain dear friends.
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American Pie is about at ’90s as it gets, and Fulong and Lyonne, who “were together for a while,” attended the 1999 premiere of the movie together.
In an interview with her friend Chloë Sevigny for Harper’s Bazaar in 2014, Lyonne says she “was crazy for him on the [Detroit Rock City] movie set,” in which the two costarred.
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Rimes and Keegan met as teenagers, she told The Sydney Morning Herald in 2022, and were first connected after she spotted him in a magazine.
“I started dating Andrew Keegan at 15,” she told the paper. “He was an actor in teen movies and we were together for three years. While filming a video clip for my song Commitment in Santa Monica, I flicked through a Teen Beat magazine and spotted him. I told my manager and hair and make-up artist that I thought he was cute. Next minute, my then manager called Andrew and asked if he wanted to meet me; that’s how we hooked up.”
Keegan now shares daughter Aiya Rose with Arista Ilona while Rimes is married to Eddie Cibrian and is stepmother to his two sons.
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After meeting in 1995, Jewel and Penn had a brief romance, which she discussed in her book Never Broken: Songs Are Only Half the Story.
After seeing her perform on Late Night with Conan O’Brien, Penn reached out to Jewel over the phone — a move her Alaska-based father first wrote off as a prank call.
“One day my dad came to find me, saying, ‘Jewel, you must be getting some kooky fans out there in the Lower 48. Some guy just prank-called and said he was Sean Penn,’” she wrote. After asking her to compose a song for a movie he was working on, the two met and she found him “charming, witty, and bright.”
Penn now shares two children with ex-wife Robin Wright while Rimes shares one son with ex Ty Murray.
Kathy Griffin/TikTok
The two comedians dated in the 1990s though in a post to TikTok earlier this year, Griffin said “dating is a very loose term.”
“This is a picture of me and my then-boyfriend, Jack Black, who you probably know mostly from School of Rock,” she wrote alongside the throwback shot. “So he was the first boyfriend I ever had where other bros thought I was cool because I was dating him.”
Griffin recalled their relationship further on TikTok, remembering a time she said, ” ‘I need a shower towel.’ And he goes, ‘You’re standing on it. ‘ … You guys, that’s straight guys. He had one bath mat/towel that he used for both, and that was it. So naturally, I kept sleeping with him.”
In her book she writes that the pair “went out only two or three times, but that’s a relationship in my book.”
Wilson and Barrymore, seen here in 1999, dated for a few years in the late 1990s, though years later the talk show host told Kate Hudson that for at least some of their time together it was an “open relationship.”
Hudson remembered meeting Barrymore for the first time while she was at dinner with Wilson, to which Barrymore responded, “I was dating him, but I think he was also dating other people … “It was an open relationship; we were young.”
“We’re just young, we’re having fun, we’re all playing, acting, hanging out,” Barrymore continued. “You’re not taking it all so seriously, and it was fun and we had the best time.”
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Luke’s older brother Owen was all loved up with then-girlfriend Crow at the 2000 premiere of Shanghai Noon. Per E! News, the pair began dating in 1999 after meeting on the set of The Minus Man and dated for two years.
Crow is now mom to her two sons Wyatt and Levi.
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Friedle was on deck to support Hewitt at the 1997 premiere of I Know What You Did Last Summer in Hollywood. The following year, Hewitt appeared on Friedle’s show Boy Meets World as his character’s love interest. And while the episode might be a fan favorite, Friedle said on an episode of the Pod Meets World podcast last year that the “super intense” makeout scene the two filmed is “uncomfortable” to watch now.
Hewitt now shares three kids with her husband Brian Hallisay. Friedle married his wife Susan Martens in 2016.
