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21 Surprising Celeb Couples You Had No Idea Dated

Wait.. they dated?!
kimkardashian

Some stars can have pretty interesting dating lives, but it seems that the public always knows and remembers who the biggest stars have dated in the past! Surprisingly though, apparently some couples just don't get the tabloid coverage you would think they'd get so nobody actually finds out about them! See how many of these celebrity couples you knew actually dated, and which ones you had no clue even knew each other! 

Nick Cannon and Kim Kardashian

Wait... what? I can't be the only person who had zero idea that Nick Cannon and Kim Kardashian dated! Apparently back in 2006 before Kim met Kanye and Nick met Mariah the pair briefly dated, who knew!

Josh Hutcherson and Vanessa Hudgens 

Usually Disney star couples are pretty well known but this is one I definitely had no clue ever existed. The pair met on set of their movie 'Journey 2' in 2011 and had a brief fling back in the day!

Robert Downey Jr and Sarah Jessica Parker 

This is definitely a random one, around 1984 the pair got together but the relationship ended in 1991 and apparently it didn't end well. Sarah Jessica Parker went as far as to tell that media that dating Jr was like parenting a teenager.. yikes.

Winona Ryder and Matt Damon 

These two stars met in 1997 thanks to Gwyneth Paltrow and maintained a 3 year relationship before breaking it off. While it does seem like an odd pairing they look so cute together!

Matthew McConaughey and Janet Jackson 

This fling is definitely one of the more random ones on this list for sure. After meeting during the 2002 Grammys, rumours say the pair had an extremely short but sweet romance.

Cameron Diaz and Jared Leto 

This acting pair dated from 1999 to 2003 and were actually engaged before breaking up. Luckily the two both say they've got nothing but love for each other!

Sofia Vergara and Enrique Iglesias

I still can't believe this one is real! Before Sofia Vergara blew up for her role on Modern Family, she was famous for dating Enrique Iglesias back in the day. Yea- the tables have definitely turned in regards to who's got more fame now.

Tom Cruise and Cher 

How Tom Cruise and Cher crossed paths in the first place is a question I continue to ask myself but apparently they did and really hit it off. Cher spoke about it in an interview claiming that she was crazy about the actor, 39 at the time, and they had a brief fling regardless of him being 16 years her junior. She even went as far as to say he was one of her "top five favourite lovers."

Shia LeBeouf and Hillary Duff 

These two had an extremely brief but not so sweet dating experience. According to Duff, Shia took her out on a first date and it was their last. The date ended up going horrible and the two never saw each other again, Duff going as far to tell media outlets it was the worst date ever!

Leonardo Dicaprio and Naomi Campbell 

It comes as no surprise that Leo was attracting top models the minute his career took off because he's still attracting them now! Apparently the pair had a brief fling during 1995 but nothing materialized into a serious relationship.

Madonna and Michael Jackson 

The King and Queen of Pop would have been an iconic duo, but they never got their chance. Back in the 90's the pair had a fling but before it could turn into a relationship, Madonna's criticism of Jackson on live television resulted in him dumping her!

Madonna and Vanilla Ice 

Ok.. this is a weird one. Apparently Madonna and Vanilla Ice not only dated, but Vanilla Ice was the one who broke up with her! The pair were in a relationship up until Madonna published her book 'Sex' which contained an exploitive photo of her and Ice that he didn't approve of. He was so mad about it he broke up with her shortly after!

Jennifer Aniston and Paul Rudd 

I am so here for this couple. Aniston and Rudd had a short relationship after meeting on set of their movie 'The Object Of My Affection' in 1988. They even met again on set after breaking up on Friends, so they must have ended on good terms!

Michael Keaton and Courtney Cox 

Jennifer Aniston isn't the only Friends star to have an interesting dating past. Courtney Cox and Michael Keaton were together for a whopping 6 years before breaking up in 1995! They ended on great terms as Cox has come out since then to say Keaton is "the most wonderful person" she's ever met!

Justin Timberlake and Fergie

With Timberlake just 16 and Fergie 23, their short relationship in 1996 definitely was not meant to last. After the short fling, Timberlake got with Britney Spears which brought us the ever so iconic matching denim number at the AMA's.

Ryan Gosling and Sandra Bullock

Yea.. this was a thing. The pair met in 2002 on the set of their movie "Murder By Numbers and it definitely was an odd match.

Christian Bale and Drew Barrymore

This short fling ended on the wrong note after Bale revealed that after taking the star out for one date, she never called! Barrymore didn't stay silent on the matter either as she told media outlets that she never called because she just didn't like him!

Lance Armstrong and Ashley Olsen

The pair were first spotted together in October of 2007. With Olsen being 15 years his junior, the athlete was urged to dump her and ended up following through several months later.

Nicolas Cage and Brooke Shields

In 1987 the odd pair were rumoured to have gotten together after appearing on the 'Moonstruck' red carpet together for the first time. Shortly after though the pair broke it off.

Robbie Williams and Cameron Diaz

The singer and actress met in 2003 and engaged in a brief summer fling before Diaz moved onto Justin Timberlake!

Seal and Tyra Banks 

The singer and model dated briefly in 1996 after Banks caught Seal's attention regardless of her being 11 years his senior!