20 Celebrity Couples Who Once Dated Before They Hit The Big Time

The world of showbiz can seem like a small place at times, but occasionally it turns out it’s even smaller than you think. Every now and again, it turns out a pair of famous celebrities were actually an item long before Hollywood came calling. And some of them kept it pretty far under the radar, too. These 20 couples all dated before becoming famous, and some of them may make you go, “Wait, what?”

20. Rashida Jones and Tobey Maguire

Before he was cast as Spider-Man in the 2002 blockbuster of the same name, and before she appeared on Freaks and Geeks, Rashida Jones and Tobey Maguire dated. They lasted from 1997 to 2000. But since then they’ve both moved on with other people, although neither are married at the moment.

19. Lisa Kudrow and Conan O’Brien

Lisa Kudrow will forever be known as Phoebe Buffay. But before she took on that role in 1994, she dated Conan O’Brien after meeting him at an improv class. She revealed the story in 2011, saying that he helped her pursue comedy. But the romance didn’t last and they remained just Friends.

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18. Courtney Love and Edward Norton

It’s hard to think of a couple more mismatched than Oscar-nominated actor Edward Norton and rock wild-child Courtney Love. But, after meeting on the set of The People vs. Larry Flynt, they had an on-off relationship from 1995 to 1998. In 2006, moreover, Love told The Sunday Times that she wished she’d married him.

17. Alyssa Milano and David Arquette

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The most famous woman David Arquette’s been associated with is still his ex-wife, Friends star Courteney Cox. However, he did actually date actress Alyssa Milano in the ’90s, when he was 20 and she was 19. But these days that fling is confined to the great dustbin of forgotten celebrity relationships.

16. Jessica Biel and Chris Evans

Chris Evans became an international star when he was cast as Captain America, but back when he was a little-known actor he was also the boyfriend of Jessica Biel. In fact, they dated between 2001 and 2006. One Valentine’s Day the pair even went skydiving, which must have been good preparation for their future action roles!

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15. Rihanna and Shia LaBeouf

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It’s downright bizarre to think of these two together, but it really did (more or less) happen. In 2007, before LaBeouf was as famous as he is now, the pair went on a date. In 2009 the actor told Playboy how it went: “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”

14. Megan Fox and David Gallagher

Before she was one of the world’s most famous sex symbols, Megan Fox dated the incredibly lucky actor David Gallagher from 2003 to 2004. Reportedly, she cheated on her first boyfriend, Ben Leahy, to be with him, but it didn’t work out in the end. Now, Fox is married to Brian Austin Green.

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13. Reese Witherspoon and Jeremy Sisto

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In 2015 actor Jeremy Sisto revealed on Reddit that he’d once dated none other than Reese Witherspoon. Back when she was an unknown, they appeared in a TV movie together and started going out. “We had a long-distance relationship for a long time. I was so into her,” he wrote. However, they broke up in 1993.

12. Thandie Newton and Brad Pitt

Before he was an A-lister, before Angelina Jolie and even before Jennifer Aniston, Brad Pitt found love in the arms of the then-unknown Thandie Newton. He met her on the set of Interview With the Vampire in 1994, dated her for a bit, and then they went their separate ways. They stayed friends, though.

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11. Kristen Bell and Matt Morrison

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These days, actress Kristen Bell is married to actor Dax Shepard. But in her college days she was involved with a different celebrity: Glee star Matt Morrison. “We actually dated very briefly,” she told Us Weekly in 2010. “So I’ll have to say maybe Matt Morrison is my favorite part of Glee for various reasons.”

10. Amanda Seyfried and Alexander Skarsgård

Prior to making it really big in 2007, Amanda Seyfried dated actor Alexander Skarsgård. However, she kept it under the radar and only confirmed the relationship in 2011. She might have figured she had a good reason to, as she actually left him for her Mamma Mia! co-star, Dominic Cooper.

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9. Emily VanCamp and Chris Pratt

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Before Chris Pratt became the man of the hour, and even before he got his breaking role on Parks and Recreation, he dated his Everwood co-star (and onscreen sister!) Emily VanCamp. The pair split in 2007, and now they both have roles in the blockbuster Marvel franchise. Could get awkward if their characters ever meet.

8. Tyra Banks and Seal

As everyone most likely remembers, Seal was once in a power-couple with supermodel Heidi Klum. But before that he dated a different model, Tyra Banks. The relationship began in 1992 and ended in 1996, but they kept it on the down-low. Indeed, the fact that they went out is all but gone from memory.

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7. Keira Knightley and Jamie Dornan

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Keira Knightley and Jamie Dornan are both big stars now, but back in 2003 they were a pair of struggling young actors trying to make good. And the fact that Keira succeeded first may have been the death knell for their relationship. The pressures of fame overtook them, and she was reportedly devastated when they split in 2005.

6. Carol Kane and Woody Harrelson

After Woody Harrelson was cast in Cheers but before he got mega-famous, he dated Annie Hall actress Carol Kane. It started in 1986 and ended two years later, but not on bad terms. “We had a friendship that became a romance and then a friendship again,” Harrelson told People magazine in 1988.

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5. Sarah Jessica Parker and Robert Downey Jr.

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Long before he became Iron Man, Robert Downey Jr. dated Sarah Jessica Parker. It lasted from 1984 to 1991, prior to Sex and the City, so she hadn’t hit the big time yet, either. Now both are older, more successful, and wiser. They even reconnected as friends in 2016.

4. Melissa Joan Hart and Ryan Reynolds

Sabrina the Teenage Witch and Deadpool once dated?! Yep, they did. Before either Melissa Joan Hart or Ryan Reynolds were famous, they had a fling on the set of a 1996 Sabrina movie. In fact, Hart revealed in a 2013 memoir that she actually cheated on her boyfriend with him!

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3. Jennifer Garner and Michael Vartan

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Jennifer Garner’s most famous relationship was her marriage to Ben Affleck, of course. But before that, and before she was as known as she is now, she dated her Alias co-star Michael Vartan from 2003 to 2004. In the wake of the juggernaut that the tabloids dubbed “Bennifer 2.0” (Affleck previously dated Jennifer Lopez), it’s been completely forgotten.

2. January Jones and Ashton Kutcher

When January Jones was just starting out as an actress, she dated a guy who, she claimed, wasn’t supportive of her acting. So she ditched him! And later on, in 2009, she heavily implied almost to the point of confirmation that the bad boyfriend was fellow actor Ashton Kutcher.

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1. Rachel Lindsay and Kevin Durant

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Rachel Lindsay shot to fame as the first black Bachelorette to ever appear on the reality show Bachelor series. But she had another claim to fame, too. According to a source who went to Us Weekly, she once had a serious relationship with NBA star Kevin Durant when both were in college.

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