Whaaaa? 16 Celebs You Never Knew Dated Each Other

Whaaaa? 16 Celebs You Never Knew Dated Each Other

Whaaaa? 16 Celebs You Never Knew Dated Each Other

Thumbnail: 
Madonna in Interview magazine talking about dating, love, and sex
Dek: 
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.

 

 

List images or animated gifs: 

Howard Stern got Madonna to finally confirm a long rumored romance with the late rapper Tupac Shakur. The couple briefly dated in 1994.

<a href="http://www.imdb.com"/>1. Madonna and Tupac Shakur</a>

1. Madonna and Tupac Shakur

Lance Armstrong had a brief fling with Ashley Olsen in 2007 (um, ew).

<a href="http://www.popsugar.com/Lance-Armstrong-Denies-Dating-Ashley-Olsen-813936">2. Lance Armstrong and Ashley Olsen</a>

Roger Ebert and Oprah went on a few dates way back when.

<a href="http://blog.zap2it.com/pop2it/2010/03/roger-ebert-speaks-again-on-oprah.html"> 3. Roger Ebert and Oprah </a>

Before she hooked up with David Arquette, Courtney Cox was with Michael Keaton from 1989-1995.

<a href="http://www.mamamia.com.au/entertainment/they-dated-20-forgotten-celebrity-couples/">4. Michael Keaton and Courteney Cox</a>

And before he became Mr. Courtney Cox, David Arquette dated Drew Barrymore in 1991.

<a href="http://www.usmagazine.com/celebrity-news/pictures/drew-barrymores-love-life-2012212/20950">5. Drew Barrymore and David Arquette</a>

After a brief relationship, Lisa Kudrow and Conan O’Brien decided they were better off as friends.

<a href="http://www.ivillage.com/surprising-celebrity-couples-taylor-swift-reaction-faces/1-a-521661">6. Lisa Kudrow and Conan O'Brien</a>

Back in the days when Ashton Kutcher was just a dude looking for his car, he was also a dude dating January Jones.

<a href="http://www.usmagazine.com/celebrity-news/pictures/ashton-kutchers-love-life-201222/20470">7. Ashton Kutcher and January Jones</a>

Though their relationship only lasted from 1995-1996, Jennifer Love Hewitt and Joey Lawrence were a 90s dream couple.

<a href="http://www.tvguide.com/celebrities/joey-lawrence/photos/157668/24433">8. Jennifer Love Hewitt and Joey Lawrence</a>

Before all his other famous ladies, Ryan Renolds was linked to Kristen Johnston in 1999.

<a href="http://www.cafemom.com/group/33197/forums/read/15989341/Past_Celeb_Couples_Very_Pic_Heavy">9. Kristen Johnston and Ryan Reynolds</a>

During their time at NYU, Kristen Bell and Matthew Morrison dated briefly.

<a href="http://www.celebuzz.com/2013-07-12/did-you-know-they-dated-kristen-bell-and-matthew-morrison/">10. Kristen Bell and Matthew Morrison</a>

Before her Derek Jeter years, Minka Kelly was with Donald Faison.

<a href="http://www.zimbio.com/photos/Donald+Faison/Minka+Kelly">11. Donald Faison and Minka Kelly</a>

Seal had a flash in the pan romance with Tyra Banks in the mid-90s.

<a href="http://www.nydailynews.com/entertainment/gossip/odd-celeb-couples-dated-gallery-1.31326">12. Tyra Banks and Seal</a>

Enrique Iglesias and Sofia Vergara were once an item.

<a href="http://theinsider.etonline.com/gossip/40647_They_Dated_Surprising_Hookups/?page=19">13. Sofia Vergara and Enrique Iglesias</a>

Seth McFarlane spent time with Amanda Bynes in 2008, despite an age difference of 12 years.

<a href="http://www.eonline.com/news/3032/amanda-bynes-and-the-joy-of-seth">14. Amanda Bynes and Seth MacFarlane</a>

Modern Family's Julie Bowen was attached to David Spade in 2002.

<a href="http://www.flickr.com/photos/emaonline/6963060015/">15. Julie Bowen and David Spade</a>

Kieran Culkin bagged Anna Paquin (for a brief period) in 2007.

<a href="http://24.media.tumblr.com/tumblr_ly13ctESZ31r5xsw9o1_400.jpg">16. Kieran Culkin and Anna Paquin</a>
Join the Conversation