How did they even meet???

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Vanilla Ice and Madonna

Vanilla Ice and Madonna dated for 8 months back  in the 90’s, but Ice,whose real name is Robert Van Winkle, broke it off when Madge publishedher coffee table book SEX which features the two in sexualpictures as well as photos of Madonna with other men. “It wasdisgusting and cheap,” Vanilla Ice said in an interview, “We were in arelationship yet it looked like she was screwing all these otherpeople.” Though, he also said she was a “great lover.”

Britney and potty mouth, Irish actor Colin Farrell met when she visited the set of his movie S.W.A.T. back in 2003.  The next week the two were strolling down the red carpet hand-in-hand during the premiere of his movie The Recruit.The pair was seen hugging and kissing on two occasions at differentnightclubs. It was short-lived and Colin claimed Britney was “just amate.”

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Another head scratcher, 50 Cent and Chelsea Handler began dating after Fiddy was a guest on her show Chelsea After Dark in 2011. The rapper pursued her, which led to a several month long romance that abruptly ended later that year over an issue involving his ex, singer Ciara.


This relationship is definitely strange, but it would be a lot stranger if Madonna wasn’t such a weird cookie herself. Dennis and Madonna dated for 2 months in 1994. Weirder still, Rodman was once married to Carmen Electra.


That’s right, kids, long before there was a Tom and Katie there was Tom and Cher. The two had a brief romance in 1985 when she was 39 and he was just 23.


Who knows how these two ended up together but they were in a long-term relationship for 9 years! The couple Macaulay Culkin and Mila Kunis was reportedly engaged but split in 2011.

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Life and Style magazine reported that the Cameron Diaz and P Diddy were seen “making out and acting romantic” back in December 2011. The rumor of their relationship continued into the next year.


Yeah, we didn’t know either! The two urban hit makers dated back in 1997 when Justin Timberlake was just 16 and Fergie was 23. She reportedly admits to the relationship, though, she regrets it now due the age difference. Her friends used to call her “Stella” (as in How Stella Got Her Groove Back).


It might be an odd pairing, but we can’t blame Sandra for wanting her some Ryan Gosling. They started dating during filming of the 2002 movie Murder By Numbers. They dated for a year. Bullock’s friend, and fellow actor Hugh Grant used to refer to Ryan as “The Child.” Gosling is 16 years her junior! And get this, he says til this day that she and former flame Rachel McAdams were the “best girlfriends ever.”

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