Whaaaa? 16 Celebs You Never Knew Dated Each Other

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Buzz, Love

Stop the bus. She dated who?

Madonna recently dropped a bombshell about her dating past, but she's not the only celeb with some random ex skeletons in her closet. Everybody remembers flashy celebrity weddings (and the often times disastrous marriages that follow), but what about the flings that came before? What about the strange hookups and relationships that some celebs would rather leave buried? Well, we dug them up! Behold, celebs you didn't know dated one another.

 

 

Howard Stern got Madonna to finally confirm a long rumored romance with the late rapper Tupac Shakur. The couple briefly dated in 1994.
Lance Armstrong had a brief fling with Ashley Olsen in 2007 (um, ew).
Roger Ebert and Oprah went on a few dates way back when.
Before she hooked up with David Arquette, Courtney Cox was with Michael Keaton from 1989-1995.
And before he became Mr. Courtney Cox, David Arquette dated Drew Barrymore in 1991.
After a brief relationship, Lisa Kudrow and Conan O’Brien decided they were better off as friends.
Back in the days when Ashton Kutcher was just a dude looking for his car, he was also a dude dating January Jones.
Though their relationship only lasted from 1995-1996, Jennifer Love Hewitt and Joey Lawrence were a 90s dream couple.
Before all his other famous ladies, Ryan Renolds was linked to Kristen Johnston in 1999.
During their time at NYU, Kristen Bell and Matthew Morrison dated briefly.
Before her Derek Jeter years, Minka Kelly was with Donald Faison.
Seal had a flash in the pan romance with Tyra Banks in the mid-90s.
Enrique Iglesias and Sofia Vergara were once an item.
Seth McFarlane spent time with Amanda Bynes in 2008, despite an age difference of 12 years.
Modern Family's Julie Bowen was attached to David Spade in 2002.
Kieran Culkin bagged Anna Paquin (for a brief period) in 2007.

 

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