WTF Celebrity Couples

You think you know all the celebrity couples, don't you? Angelina & Brad. Jennifer & Ben. Gwyneth & Chris. And the list goes on.

But today, I'm going to introduce you to some celebrity couples you might not have realized existed. And they are mostly couples that seem...mismatched in a way.

They might make you scratch your head and say, "wait, she dated him?!"

Enjoy.

Ashton Kutcher and January Jones (1998-2001)

Long before the success of Mad Men, January Jones was just another 20-something girl desperate to make a name for herself in Hollywood. But her famous television actor boyfriend, Ashton, was not her biggest fan.

 "He was not supportive of my acting," Jones told GQ in 2009. "He was like, 'I don't think you're going to be good at this.' So, fuck you!"

Strangely enough, last year there was a huge rumor in Hollywood that January Jones was the reason for the Ashton/Demi split. A popular, and mostly reliable, gossip column insinuated that Ashton was the father of January's son, and Demi was less than pleased by the news.

Matt Damon and Winona Ryder (1997-2000)

The two were introduced in 1997 by mutual friend, Gwyneth Paltrow. It was love at first sight. But they didn't make their romance public until a year later, at an Oscar party.

Despite the break-up, the two remain on pretty good terms right now. They have nothing but nice things to say about each other in interviews.

But the media blitz while he was with Winona may have been the reason Matt chose to marry an obscure bartender several years later. The action star is known for living a modest life.

P.Diddy and Sienna Miller (2007)

Five years ago, the dainty British beauty and the American rap mogul raised eyebrows when they were spotted frolicking on exotic vacations together and sailing the seas in Diddy's jaw-dropping yacht.

Despite protest on both sides, photos spoke louder than words. Photos of them cuddling together during wee hours of the morning outside hotels were plastered all over supermarket tabloids.

But, they must have parted amicably because a year later, Diddy told Vogue he thought Sienna was one of the most stylish and poised women in the world.

Michael Jackson and Brooke Shields (1991-1993)

This unlikely duo became friends in the early 1980s, after meeting at an Academy Awards ceremony. But they didn't begin dating until a decade later. Michael actually asked Brooke to marry him, but when she declined, they simply remained close friends until his death.

In 2001, Michael revealed in an interview how he felt meeting Brooke in the early 1980s: "That was one of the loves of my life. I think she loved me as much as I loved her, you know? We dated a lot. We, we went out a lot. Her pictures were all over my wall, my mirror, everything...we exchanged numbers and I was up all night, singing, spinning around my room, just so happy. It was great."

Justin Timberlake and Fergie (1998)

In interviews, Fergie confesses the 1990s were a whirlwind of sex and drugs and pop music. In 1996, she was a member of the girl band, Wild Orchid, which opened for 'N Sync. The future pop star had a brief fling with an underage Justin.

 "It wasn't a long-term serious relationship, so there's no bad blood," says Fergie to Australia's Courier Mail. "He was 16 and I was 23...It was before he got real heavy with Britney."


So, do any of these past romances surprise you? Which one shocked you the most?