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Can You Believe They Dated?

Oprah and Roger Ebert, Dennis Rodman and Madonna & other odd exes

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    Curb Your Enthusiasm star Ted Danson had an affair with Whoopi Goldberg in 1993. Danson was still married to Casey Coates at the time and the affair resulted in one of Hollywood's most epensive divorce settlements costing $30 million.

    Photo: Getty Images

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    Childhood friends, Michael Jackson and Brooke Shields decided to give a relationship a try in the early 1990s. Despite never confirming details of the relationship, Shields gave a tearful speech at Jackson's memorial service.

    Photo: Getty Images

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    Married from 1992 to 1996, the odd-ball couple of Lisa Marie Presley and Michael Jackson met for the first time when Presley was only 7 years old. They got married within 4 months of starting to date and continued dating on and off for the four years following their divorce.

    Photo: Getty Images

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    With an 11 year age difference Seal and Tyra Banks showed up to the Essence Awards together in 1996.

    Photo: WireImage

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    Actress Halle Berry had some boy band fever in the late '80s. She and singer Danny Wood of New Kids On The Block became an item in 1989.

    Photo: Getty Images

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    Oprah and Roger Ebert went out on a few dates in 1986. Although the relationship never lasted, we can all thank Roger for encouraging Oprah to syndicate her show!

    Photo: Getty Images

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    Unexpected duo, Chelsea Handler and 50 Cent, were rumored to be dating in the Fall of 2010 after being spotted canoodling at a club in New Orleans. The paring, that Handler consistently denied, reportedly broke it off just a few months later in December.

    Photo: Getty Images

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    After meeting on the set of the movie Brick, Meagan Good and Joseph Gordon-Levitt briefly dated for about six months during 2005.

    Photo: WireImage

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    Tiger Woods "went out a few times" with country star LeeAnn Rimes before she wed her soon-to-be ex-husband Dean Sheremet in 2002.

    Photo: Getty Images

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    Common and Taraji Henson kept a pretty tight lid on their relationship, but Taraji did admit to Wendy Williams in 2011 that she and Common did in fact date!

    Photo: WireImage

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    Minka Kelly and Donald Faison surprisingly dated for about a year before they broke up in 2005.

    Photo: FilmMagic

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    Actors Brad Pitt and Robin Givens met on the set of TV show 'Head of the Class' and began dating in the midst of Robin's divorce from Mike Tyson. The couple dated for around 6 months before they eventually called it quits.

    Photo: Getty Images

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    Back in the summer of 2007, rumors had been circulating that Shia LaBeouf and Rihanna were dating after duo were spotted eating together in Beverly Hills. LaBeouf later admitted to going on one date, but it didn't work out after that.

    Photo: Getty Images

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    In 1988 after speparating from her then-husband make-up artist Ron Snyder-Britton, Kim Basinger dated Prince!

    Photo: Getty Images

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    Rosario Dawson and director Danny Boyle began dating in 2012 after she was cast in his movie Trance. The couple, who was very private about their relationship, went their separate ways in 2013.

    Photo: Getty Images

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    Jermaine Dupri and Janet Jackson split after almost 7 years together in 2009. Apparently the duo couldn't balance work and play and cited Jermaine producing some of Janet's tracks as a point of tension in their relationship.

    Photo: Getty Images

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    Jennifer Lopez and actor Wesley Snipes dated briefly in 1994. They met during filming of the movie Money Train.

    Photo: Getty Images

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    While working on "Diary of a Mad Black Woman" together Shemar Moore and Kimberly Elise were rumored to have been dating. They were spotted getting close multiple times, but their relationship was short-lived.

    Photo: Getty Images

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    Brigitte Nielsen and Flavor Flav, reality TV's craziest celebrity couple met while appearing on VH1's The Surreal Life. The match then starred in their own reality show Strange Love which focused on their relationship and its demise.

    Photo: WireImage

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    Hip-hop super couple of times past, J-Lo and Diddy (at that time Puff Daddy) dated for two and a half years until 2000. The couple was involved in serious drama when in 1999 at a NYC nightclub when gunfire famously broke out between Diddy's entourage and another. The rapper was charged with felony gun possession.

    Photo: Getty Images

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    Strange celebrity duo, political pundit Al Sharpton and actress turned fashion designed LisaRaye were paired in 2009.

    Photo: FilmMagic

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    Karrine Steffans, author of Confessions of a Video Vixen, unexpectedly started dating late night host Bill Maher in 2005.

    Photo: WireImage

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    Ray J and Whitney Houston, were spotted getting close in a night club in November 2010 after allegedly breaking off their relationship a year earlier. Houston, who was 17 years older than Ray J, began dating him after her divorce from Bobby Brown.

    Photo: Getty Images

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    Dennis Rodman and Vivica A. Fox were rumored to have briefly dated in 1997. Their relationship was never confirmed but she did take him as her date to the Academy Awards!

    Photo: Getty Images

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    In an unexpected move, Carmen Electra and Dennis Rodman were hitched in a quickie Vegas wedding in 1998. The marriage didn't last very long, and they split after less than a year.

    Photo: Getty Images

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    Madonna had also dated Dennis Rodman in 1994. She wanted to have his baby!

    Photo: Splash News

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    Ray J has a thing for the name Kim. He and rapper Lil Kim were rumored to have been an item in 2007, after they showed up to a party together holding hands.

    Photo: Getty Images

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    Mos Def and Beyonce were rumored to have been an item right before Queen Bey started dating Jay Z in the early 2000s.

    Photo: FilmMagic

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    In early 2007, Sienna Miller and P Diddy were spotted looking cozy in Park City. This sparked rumors that the pair were dating. They were photographed a few more times afterwards but were never confirmed as a couple.

    Photo: WireImage