Whaaaa? 16 Celebs You Never Knew Dated Each Other

Photo: celebuzz
16 Celebs You Never Knew Dated Each Other
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.
<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>

2. Lance Armstrong and Ashley Olsen

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>

3. Roger Ebert and Oprah

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>

4. Michael Keaton and Courteney Cox

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>

5. Drew Barrymore and David Arquette

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>

6. Lisa Kudrow and Conan O'Brien

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>

7. Ashton Kutcher and January Jones

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>

8. Jennifer Love Hewitt and Joey Lawrence

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>

9. Kristen Johnston and Ryan Reynolds

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>

10. Kristen Bell and Matthew Morrison

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>

11. Donald Faison and Minka Kelly

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>

12. Tyra Banks and Seal

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>

13. Sofia Vergara and Enrique Iglesias

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>

14. Amanda Bynes and Seth MacFarlane

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>

15. Julie Bowen and David Spade

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>

16. Kieran Culkin and Anna Paquin



Explore YourTango