10 Celebs You Won’t Believe Were Once A Loved Up Couple

We’ve all made mistakes in the dating world. Looking back on your past, there are probably a few guys and gals in there who have left you scratching your head.

“Was I drunk?” – you ask. “Did I really go there, or am I confusing my past with someone else’s?”

“Was I really that desperate?!”

And there are always those mistakes for which there are no other words except Oh. My. Goodness.

But dating disasters are nothing new, and the good thing is that you can move on with your life and forget all about them. With a simple click on Facebook, they’re deleted, gone for ever!

But sometimes you get things so right that you can look back and think, “Boy, did I date some great people!”

And let’s not forget the time you dated that hottie for a few weeks who you thought was way out of your league.

In celebration of getting things wrong, getting things weird, and getting things occasionally awesome, let’s take a look at 10 celebs you won’t believe were once a loved up couple.

Angelina Jolie & Billy Bob Thornton

Right now, it feels as though Angelina Jolie and Brad Pitt have been together forever, but they only got together in 2005, after Jolie had already adopted three children. Before “Brangelina” became a thing, Angela was dating Bad Santa star Billy Bob Thornton.

In fact, the pair only dated for just two months before they got married in Vegas in 2000. Although they divorced almost exactly three years later in May 2003, the couple did adopt a child together and wore each others’ blood in vials around their necks. Cute.

When I asked my husband to do the same, he said No. Hmph.

Michael Jackson & Lisa Marie Presley

To some of our readers, Michael Jackson is and always will be the King of Pop. Famous for eighties hits such as Billie Jean and Beat It, he was the coolest dancer in town who invented the Moonwalk and wowed audiences all over the world. Take a step back, Minaj.

To others who are too young to remember, Jackson is probably most famous for dying under controversial circumstances on the eve of his comeback tour.

But what you may or may not know is that during the peak of his powers, the most famous Jackson Five once dated Elvis Presley’s daughter, Lisa Marie. He first met her in 1974, married her in 1994 and even wrote a song about her called You Are Not Alone.

Katy Perry & Russell Brand

These days, it’s hard to believe that sworn bachelor and loudmouth Brit Russell Brand once married anyone, let alone feisty U.S. singer Katy Perry.

Their courtship didn’t last long before Russell got down on one knee and proposed, and the actual marriage lasted even less. It always seemed like a marriage that was doomed from the start; after all, Brand has always been known more for his sexual exploits than anything else, while Katy once kissed a girl and liked it. Were these two really cut out for marriage? Probably not.

Tom Cruise & Cher

It’s hard to believe nowadays that 69 year-old Cher once dated Tom Cruise. But when you consider that Cruise is actually fifty-two already, the age gap doesn’t seem that great.

Cher, who says she turned down the advances of Marlon Brando and Elvis Presley, claims that Cruise is one of her top five former lovers.

“I had just the greatest lovers ever,” she boasted. “Not a long list, just a good list.”

Cruise and Cher dated in the eighties, before his career developed wings.

Pamela Anderson & Michael Jackson

Jackson is back, this time with former Baywatch star and plastic surgery veteran, Pamela Andeson.

Jackson and Anderson are rumoured to have dated in 2008, not too long before Michael’s early death. Sources claim that the pair were a very strange couple who “hit it off in total secrecy.”

We’re not quite sure why Jackson didn’t want to show off to the world that he was dating former Playboy cover star Anderson, but each to their own.

Frank Sinatra & Mia Farrow

What’s perhaps most surprising about hunky old blue eyes and dainty Mia Farrow getting married is less that they had an age gap of three decades, and more that it took wacky comedian Woody Allen to break them up.

Okay, perhaps Allen was in no way responsible for the pair getting divorced, but once Sinatra was out of the picture, Farrow got hitched to the film director and had a few kids with him.

When you compare photos of Frank and Woody, it’s hard to know what Mia was thinking. Guess she just did it her way.

Kiefer Sutherland & Julia Roberts

These days, Kiefer Sutherland is world famous for playing the role of CTU field agent Jack Bauer in smash-hit U.S. crime drama 24. But before 24, Sutherland was reduced to taking roles in low-budget films that no one ever watched, such as the excruciating Freeway.

In fact, his only real claim to fame was that he came within inches of marrying Pretty Woman star Julia Roberts in 1991. He was pretty much jilted at the altar when Roberts broke off their engagement after over a year. Even the wedding cake was ready!

Nicholas Cage & Lisa Marie Presley

After her brief fling with Michael Jackson that resulted in him penning a song about her not being alone, Lisa Marie Presley eventually felt so alone that she ran into the arms of action hero Nicholas Cage.

The couple got wed in August 2002, but by November Cage quickly filed divorce papers. They say that love is fleeting in Hollywood.

Ryan Gosling & Sandra Bullock

Back in 2002 when Ryan Gosling was still largely unknown to everyone except his family, he dated superstar actress Sandra Bullock. The relationship fizzled out after just a few months, but Gosling continues to look back fondly, saying that he had “two of the greatest girlfriends of all time. I haven’t met anybody who could top them.”

Moby & Natalie Portman

There was a time when the whole world thought that Moby was gay.

But then he went and dated Natalie Portman, arguably one of the hottest women on the planet.

The relationship didn’t last long, with Moby confessing that it “made me the target of a lot of nerd wrath.”

Naturally, it wasn’t just nerds who were jealous of Moby. It was every living male.

Stay happy!

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