The 1990s were a special time. Watching TGIF was the best thing to do on a Friday night, the original 90210 was still on the air, and Leonardo DiCaprio starred on Growing Pains.
Some things never change, though — stars or future stars meet and fall in love. And sometimes, the pairings are unexpected. Scroll down to see some surprising celebrity pairings… starting with a certain Grey’s Anatomy star and her then-Blossom-ing love.
Katherine Heigl and Joey Lawrence
Katherine Heigl landed the cover of Seventeen in 1994, when she was just a 15-year-old model and not a big time movie star. In the pages of the mag, she dished on her relationship with Joey Lawrence, who was starring on Blossom at the time.
“Kiss From a Rose” singer Seal sure has a type — supermodels-turned-TV-hosts? Heidi Klum’s ex-husband dated America’s Next Top Model host Tyra Banks in 1996, nine years before he’d marry the Project Runway host.
Courtney Love and Edward Norton
Kevork Djansezian and Frederick M. Brown/Getty Images
Grunge’s hot-mess queen Courtney Love totally dated clean-livin’ Edward Norton for a minute in 1996. He was reportedly a good influence on her; they went on hikes, and she quit smoking and doing drugs.
That didn’t stop Courtney from occasionally having a big ol’ bout of being herself, though; while hiking in Scotland, the couple was halfway up Ben Nevis when Courtney decided to run back down to go to the Loch Lomond festival, where Oasis was playing. “We were fighting,” Courtney reflected to Craig Ferguson on The Late Show.“ And I thought, ‘You know what? F—k it.’ — and I went to see Oasis.”
They were on-again and off-again from 1997 through 2000 as they co-starred in Shakespeare in Love, Bounce, and other films. We’re not sure what broke them up, but Gwyneth did call the relationship “strange.”
Back when Gwyn was dating Ben, she decided to set her buddy Winona up with Ben’s bestie Matt Damon. Winona and Matt met in 1997 and immediately hit it off. Winona and Gwynnie had a falling out soon after (reportedly after Gwyn won her 1998 Best Actress Oscar), but Win’s relationship with Matt continued until 2000.
“From the moment I saw him, I realized he was the most incredible person I’d ever been so fortunate to meet,” Drew Barrymore told People about her then-boyfriend Luke Wilson in 1998. He was 27, she was 23. The two met while filming Home Fries in 1996, and, according to director Dean Parisot, got in a fight right before shooting a scene in a Lamaze childbirth class.
You read that right! Before January Jones hit the bigtime with her role as Betty Draper on Mad Men, she dated then-teen idol Ashton Kutcher. She was still an Abercrombie and Fitch model, and Ashton, she says, was less than supportive of her attempts to get into acting.
“He was like, ‘I don’t think you’re going to be good at this,’” Januaryreflected to GQ in 2009. “He only has nice things to say now — if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.”
While Lance Bass was still very much in the closet, he was the steady guy of Boy Meets World sweetheart Danielle Fishel. He even took her to prom!
The two remain friends, and Danielle, as far as we know, still hasn’t gotten rid of her “Lance Box.” Danielle got hitched to hubby Tim Belusko in October 2013; Lance wed his longtime boyfriend Michael Turchin a year later.
Matthew McConaughey and Sandra Bullock met while filming the heavy 1996 drama A Time to Kill. “He’s become a powerful force in my life,” Sandra said at the time — while denying dating Matthew. She added, “We have fabulous chemistry together.”
“We both have a lot of strong feelings for each other, but it’s not the right time right now,” Matthew reflected in 2001, once the romance had cooled, “It wasn’t the right time before. I do love her and will always love her. Absolutely.”