Odd Couples: The Most Surprising Celebrity Duos

Posted by , on August 22, 2012 at 4:00 pm
Avril Lavigne and Chad Kroeger: These two Canadian-born rockers just upgraded their relationship status to engaged after only six months of dating under the radar. Their unexpected announcement came as a [...]
Avril Lavigne and Chad Kroeger: These two Canadian-born rockers just upgraded their relationship status to engaged after only six months of dating under the radar. Their unexpected announcement came as a complete surprise to many as no one even knew they were an item.

Natalie Portman and Moby: When Natalie Portman, one of Hollywood’s hottest actresses, got together with Moby, a geeky-looking DJ and self-proclaimed nerd, jaws dropped, and rightfully so. This surprising [...]

Natalie Portman and Moby: When Natalie Portman, one of Hollywood’s hottest actresses, got together with Moby, a geeky-looking DJ and self-proclaimed nerd, jaws dropped, and rightfully so. This surprising relationship didn’t last long though. The year 2001 marked both the beginning and end of this couple’s fling.

Tila Tequila and Billy Corgan: Smashing Pumpkins frontman Billy Corgan took a shot at love with Tila Tequila, a bi-sexual dating show hostess, back in 2009 and succeeded - but only for a brief period of [...]

Tila Tequila and Billy Corgan: Smashing Pumpkins frontman Billy Corgan took a shot at love with Tila Tequila, a bi-sexual dating show hostess, back in 2009 and succeeded - but only for a brief period of time. Smashing Pumpkins fans everywhere, and most everyone else for that matter, were in shock at this incredibly random romance.

Cher and Tom Cruise: Long before Tom Cruise and Katie Holmes became one of Hollywood’s most discussed couples, he dated Cher, who is almost two decades his senior. They were one interesting couple back [...]

Cher and Tom Cruise: Long before Tom Cruise and Katie Holmes became one of Hollywood’s most discussed couples, he dated Cher, who is almost two decades his senior. They were one interesting couple back in the 1980s. But just like the popularity of big hair and leg warmers, their relationship ceased to exist.

Lisa Kudrow and Conan O'Brien: Other than their ability to make people laugh, Conan O'Brien and Lisa Kudrow don’t seem to have much in common, which most likely is the reason their short-lived romance, [...]

Lisa Kudrow and Conan O'Brien: Other than their ability to make people laugh, Conan O'Brien and Lisa Kudrow don’t seem to have much in common, which most likely is the reason their short-lived romance, which began when he was a writer for "Saturday Night Live" and she was a comedian in Los Angeles, ended before it ever really took off.

Ashley Olsen and Lance Armstrong: What do you get when you put together a Tour de France winner and a child star turned fashion designer? One strange couple. Despite a significant age difference and a [...]

Ashley Olsen and Lance Armstrong: What do you get when you put together a Tour de France winner and a child star turned fashion designer? One strange couple. Despite a significant age difference and a lack of commonalities, Ashley Olsen, 26, and Lance Armstrong, 40, decided to give dating a shot in 2007 only to break up a few months later.

Mila Kunis and Macaulay Culkin: Unlike most unexpected celebrity relationships, Macaulay Culkin and Mila Kunis’ was anything but brief. The two movie stars dated for almost a decade beginning in 2002. [...]

Mila Kunis and Macaulay Culkin: Unlike most unexpected celebrity relationships, Macaulay Culkin and Mila Kunis’ was anything but brief. The two movie stars dated for almost a decade beginning in 2002. While on the surface these stars seems to make an unlikely couple, the two apparently had a great deal in common and made a solid pair.

Renee Zellweger and Jack White: Opposites really do seem to attract, or at least in the case of White Stripes frontman Jack White and actress Renee Zellweger, who dated for almost two years. You wouldn’t [...]

Renee Zellweger and Jack White: Opposites really do seem to attract, or at least in the case of White Stripes frontman Jack White and actress Renee Zellweger, who dated for almost two years. You wouldn’t think White’s cool, hipster personality and Zellweger’s swanky attitude would mesh well, but something must have clicked for these two celebrities.

Sinitta and Brad Pitt: Brad Pitt has a laundry list of interesting ex-girlfriends, but Sinitta, singer and former Ms. Simon Cowell, takes the cake. When compared to his current significant other, [...]

Sinitta and Brad Pitt: Brad Pitt has a laundry list of interesting ex-girlfriends, but Sinitta, singer and former Ms. Simon Cowell, takes the cake. When compared to his current significant other, award-winning actress Angelina Jolie, Sinitta didn’t stand a chance with the hunky movie star, and ultimately, the relationship came to an end after just a couple years.

Angelina Jolie and Billy Bob Thornton: It’s difficult to imagine Angelina Jolie with anyone other than her soon-to-be husband Brad Pitt, but there were other, less compatible men in her life. Billy Bob [...]

Angelina Jolie and Billy Bob Thornton: It’s difficult to imagine Angelina Jolie with anyone other than her soon-to-be husband Brad Pitt, but there were other, less compatible men in her life. Billy Bob Thornton and Jolie eloped and remained married for about two years before Jolie called it quits and filed for divorce, making this her second failed marriage and his fifth.

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Love truly is blind, or at least when it comes to celebrity couples that is. Celebrities tend to stick to dating other high-profile personalities, giving them at least one thing in common, but just because most everyone in Hollywood is famous, that doesn’t mean they’re all a perfect fit for one another.

While most A-list relationships nowadays are overly publicized via tabloids and online celebrity gossip websites, not all superstar flings  are made public. But it’s some of these lesser-known celebrity hook ups that draw the most speculation.

Whether it be a care-free rocker pairing up with a girl-next-door type or two stars from completely different generations getting together, Hollywood has experienced its fair share of bizarre dating stories. In fact, when news broke last night of Avril Lavigne getting engaged to Nickelback rocker Chad Kroeger, we were a bit shocked. Wasn’t she dating Brody Jenner about two minutes ago? This got us thinking about odd couples.

Click through the gallery above to see some of the most shocking celebrity couples!

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