She Dated Him!? Most Surprising Celebrity Couples

December 13, 2011 By:
She Dated Him!? Most Surprising Celebrity Couples

Tom Cruise and Cher? Whoopi Goldberg and Ted Danson? Chelsea Handler and 50 Cent?

These are the most random couples, the WTF couples, the pairings that make you say "He's dating her?" and the couples that I bet you didn't know dated. Basically, these are some of the most surprising celebrity pairings.


Whoopi Goldberg and Ted Danson: Because of Whoopi Goldberg's penchant for wearing crocs and t-shirts that are about 100 sizes too large for her, I sometimes can't remember what team she plays for, but she likes men and one of her most bizarre boyfriends was when she dated Ted Danson in the early 1990's. Whoopi was actually the "other woman" because Danson was married when they met on the set of "Made in America." People were saying "whoops" when Whoopi caused Danson to divorce his wife.


Ryan Gosling and Sandra Bullock: Before Sandra Bullock was making headlines for maybe dating Ryan Reynolds several months ago, people don't remember that she dated Ryan Gosling back in 2001. Gosling was 22 and Bullock was 38 when they started dating after they met on the set of "Murder By Numbers." Sandra's friend Hugh Grant thought their pairing was so random that he referred to 16-years-younger Ryan Gosling as "The Child" and would make a sound of a baby crying whenever he came around. Obviously Cougar-Cub relationships have come and gone, but Ryan HOT Gosling and Sandra Bullock, is this not weird to anyone else?!

Kate Moss

Johnny Depp and Kate Moss: While this isn't a weird pairing per se, it's actually a perfect one and leads me to wonder why more people didn't know about it or why it didn't work out. Johnny Depp dated model Kate Moss for four years beginning in 1994. If we're talking attractiveness and bone-structure, these two were basically created for one another. I'm still freaking out that I didn't know they dated! There should be a bronze statue in their honor somewhere.


Tom Cruise and Cher: Back in the 80’s, Cher dated Tom Cruise. Cher is 16 years older than Cruise, but that’s not even the weirdest part. The weirdest part is that Cher dated Tom Cruise!! They kept their relationship a secret and Cher only went public with it a few years ago. As suspected, they only lasted a few months.

50 Cent

Chelsea Handler and 50 Cent: A lot of people now know that late night talk show host Chelsea Handler dated the rapper 50 cent, but when I first heard that they were dating I was super surprised. Chelsea finally came out about the relationship to Piers Morgan saying, "we dated, very casually." This is just so random because Handler makes her living making jokes about the Kardashians while 50 Cent makes his living rapping about how he got shot 9 times. I guess opposites attract?


January Jones and Josh Groban: "Mad Men" star January Jones, who now has a mystery baby with an unknown baby daddy proves to have a mysterious and shady dating path. She dated operatic singer Josh Groban. Yeah, that singer your mom listens to every Christmas. The couple dated for three years! How did we not know about this!? At the time they dated, January Jones was not famous at all, all articles referred to her as an "actress/model who once dated Ashton Kutcher".


Carmen Electra and Dennis Rodman: Did you know that these two were married? Carmen Electra and Dennis Rodman got married at 7am in Las Vegas, and had it annulled two weeks later. Rodman claimed he was drunk when they got married. Oh really? 7am nuptial in Vegas and you expect that to be done sober? They stayed together for almost a year even after the marriage ended but eventually were arrested after police got a domestic dispute call. That was also the end of their relationship.