Did You Know They Dated? 15 Surprise Hollywood Relationships

December 18, 2012  |  
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Hollywood relationships between two celebrities are all but expected nowadays, but there have been some celebrity hook ups that shocked us all. From a mismatched couple to a relationship that was so quick no one knew or talked much of it, there have definitely been some celebrity relationships that no one saw coming. Here are 15 of those.


Kathy Griffin & Jack Black

Jokesters Kathy Griffin and Jack Black had a brief fling together, but can you image all of the laughs these two had? Nowadays Kathy is dating Randy Bick, a guy 17 years younger. On the other hand, Jack Black is now married to Tanya Haden.

Carrie Underwood & Travis Stork

Country sweetheart Carrie Underwood dated The Doctors co-host Travis Stork back in 2008, but apparently the relationship didn’t last long. That same year Carrie Underwood met her now fiance Mike Fisher. Travis is now married to Charlotte Brown.

Jewel & Sean Penn

Back in 1995, almost 10 years ago, Jewel and Sean Penn claimed to be just friends, but their relationship was obviously more than that after the two were seen holding hands. Jewel married her long-time boyfriend Ty Murray and Sean Penn is reportedly on and off dating model Petra Nemcova.

Jennifer Connelly & Josh Charles

Jennifer Connelly and Josh Charles were an item way back in 1999. The two dated for three years but called it quits soon after. Jennifer is now married to Paul Bettany and Charles is dating Sophie Flack.

Ellen Barkin & Johnny Depp

In 1994, Ellen Barkin and Johnny Depp were an item. The two dated despite their nine-year age difference. The couple had several public apperances but didn’t last very long. Nowadays Johnny is dating Amber Heard and Ellen Barkin is dating much younger Sam Levinson.

Sharon Stone & Christian Slater

During the filming of Bobby, in 2006, co-stars Sharon Stone and Christian Slater fell for each other. Unlike many other couples on the list, Sharon and Christian went public after they appeared at the American Music Awards together that same year. However, the couple broke up after Christmas and went their separate ways. Sharon is dating Martin Mica and Christian Slater is dating Brittany Lopez.

Reese Witherspoon & Chris O’Donnell

At the ripe age of 17, Reese Witherspoon dated Chris O’Donnell in 1993. The couple were together for a few short months before calling it quits. Reese is married to Jim Toh and Chris O’Donnell is married to Caroline Fentress.

Heather Graham & Matthew Morrison

Heather Graham and Matthew Morrison had a short hook-up in 2003 and unsurprisingly they broke up the same year. The couple how since gone their own ways and Heather has been dating Yaniv Raz since 2008. Matthew is dating Lizzy Caplan.

Drew Barrymore & Christian Bale

Superman actor Christian Bale apparently went on just one date with Drew Barrymore and after that he decided she just wasn’t for him. The date wasn’t much of a hit and the two never saw the light of day together. Drew is now married to Will Kopelman and Christian Bale is married to Sandra Blazic.

Jordana Brewster & Mark Wahlberg

Quietly in 2000, Jordana Brewster and Mark Wahlberg were an item for two years. The couple stayed under the radar fairly well as they clearly knew what hot spots to avoid. Nowadays Mark is married to Rhea Durham and Jordana is married to Andrew Form.

Minka Kelly & Jake Gyllenhaal

Though we can’t exactly call this one a true relationship, it’s been rumored that Jake Gyllenhaal and Minka Kelly had a short, sweet, and secret hookup. Minka apparently first turned Jake down, but changed her mind. The hookup was nothing more than that, though, as Jake is now dating Mahsa Jafarian and Minka is with Chris Evans.

Winona Ryder & David Duchovny

In 1996, Johnny Depp’s ex-love Winona Ryder dated David Duchovny. The couple  kept their relationship on the down-low though that didn’t mean a happy ending as the two are no longer together. Winona is single and David is married to Tea Leoni.

Jessica Biel & Derek Jeter

We all know that Derek Jeter has a thing celebrity chicks and unknowing to many people, he dated Jessica Biel back in 2006. The couple called it quits by 2007. Jessica Biel is now married to Justin Timberlake and Derek Jeter is apparently dating model Hannah Davis.

Cameron Diaz & Edward Norton

Back in 1999, Cameron Diaz and Edward Norton were together, but the couple never openly admitted their relationship. They were seen getting all lovey-dovey during the 1999 Super Bowl. Cameron Diaz is dating Colin Firth and Edward Norton is engaged to Shauna Robertson.

Jessica Simpson & Billy Corgan

At some point during 2009, Jessica Simpson and Billy Corgan had a short relationship. Apparently Jessica was smitten with the Smashing Pumpkins lead singer but the couple’s relationship was kept quiet and didn’t last. Jessica Simpson is now a mom and engaged  to Eric Johnson while Billy Corgan is married to Chris Fabian.

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