Y’all Were Together For Real? Surprising Celebrity Couples We Still Don’t Understand

July 3, 2014  |  

Have you ever looked at a couple and thought, “How in the world did these two end up together?” Proving that you could find love anywhere, here’s a look at some surprising celebrity couples that made us scratch our heads.

Surprising Celebrity Couples

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Janet Jackson and Jermaine Dupri

Janet Jackson had been the object of many a man’s affection over the years. The “Rhythm Nation” singer has kept most of her relationships private, including all of her marriages. But when she found love in the arms of Jermaine Dupri, their relationship made headlines. Jackson started dating the diminutive producer back in 2001 and they remained an item for eight years. They called it quits several months before her brother Michael passed away but Dupri rushed to her side to be a shoulder for her to lean on during her time in need.

"Mila Kunis pf"

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Macaulay Culkin and Mila Kunis

Macaulay Culkin’s claim to fame was starring in the massively popular “Home Alone” franchise when he was young. As an adult, he’s stayed out of the public eye. So it was a surprise to hear that the former child star had taken up with “That 70’s Show” actress Mila Kunis. The two were dating for over eight years, keeping their relationship well under the radar, and in 2010 their split was amicable. Since then Kunis started dating her fellow sitcom co-star Ashton Kutcher and is now pregnant with their first child.

"Fergie pf"

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Justin Timberlake and Fergie

Justin Timberlake’s dating history has been public ever since he was with fellow Mickey Mouse clubber Britney Spears. But before Britney, there was Fergie. The future Black Eyed Peas singer sunk her claws into Timberlake while he was still a teenager. “It wasn’t a long-term serious relationship, so there’s no bad blood,” Fergie said in an interview with “Glamour” magazine. “He was 16 and I was 23. It was before he got real heavy with Britney.”

"Mary Kate Olsen pf"

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Mary Kate Olsen and Olivier Sarkozy

We watched her and her twin sister Ashley go from adorable toddlers to fully grown businesswomen. Mary Kate Olsen got her start in the entertainment world alongside Ashley in the sitcom “Full House.” Since then she and her sister amassed a small fortune with multiple direct-to-video films before delving into the world of fashion and creating several different clothing lines. While she’s did her best to keep her personal life away from the public eye, word seeped out that the former child star was dating Olivier Sarkozy, brother to the president of France. She’s almost half his age and almost half his size. Earlier this year it was announced that the couple got engaged.

"Ashley Olsen pf"

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Ashley Olsen and Lance Armstrong

Mary Kate isn’t the only Olsen twin who raised eyebrows with her dating partners. In 2007, Ashley caused head scratching and shoulder shrugging of her own when she was spotted making out with seven-time Tour de France champion Lance Armstrong. Fifteen years his junior, Ashley had enough sense to keep things casual with Armstrong and was long gone from his life when things came crashing down around him after admitting he had been juicing for years.

"Ashton Kutcher and Demi Moore pf"

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Ashton Kutcher and Demi Moore

Ashton Kutcher was a bachelor enjoying life when “That 70’s Show” wrapped up in 2006. The sitcom made Kutcher a wealthy man and it helped jumpstart a career on the silver screen. So it was shocking when he stepped out with Demi Moore on his arm. It was even more shocking when the pair tied the knot. Fifteen years his senior, Moore came into the relationship with three daughters. Six years later after months of speculation, the couple had announced they were splitting up.

"Courtney Love pf"

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Courtney Love and Edward Norton

Seeing Courtney Love with anyone but Kurt Cobain is a little strange but her relationship with actor/director Edward Norton was especially jarring. Maybe it was because she was the Queen of Grunge and he was a straight-laced guy who attended acting camp during his childhood. The pair managed to remain together for several years. Since their split, Norton alleges that Love still owes him some money.

"Rosario Dawson and Danny Boyle pf"

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Rosario Dawson and Danny Boyle

Some of the men that Rosario Dawson has dated in the past include Jay Z, Colin Ferrell and Joshua Jackson. And then there’s Danny Boyle. Known for his work in films like “Slumdog Millionaire” and “Trainspotting,” the English director hit it off with Dawson after she was cast in his “Trance” movie. Never mind the fact that he was 23 years older than her. Their relationship lasted about as long as their movie lasted in theaters.

"Sandra Bullock pf"

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Sandra Bullock and Matthew McConaughey

What could America’s sweetheart possibly have in common with Hollywood’s favorite bare-footed, bare-chested, bongo-playing stoner? Sandra Bullock and Matthew McConaughey dated for a brief moment in time after they met on the set of the 1996 film “A Time To Kill.” It just wasn’t written in the cards for these two to be together for long and they eventually went their separate ways. Remaining friends, McConaughey was on hand to help Bullock celebrate her Decades of Hotness gong at the Guys Choice Awards.

"Simon Cowell pf"

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Simon Cowell and Carmen Electra

What on Earth was Simon Cowell doing with Carmen Electra? The duo met each other when Electra was brought in as a celebrity guest judge for “Britain’s Got Talent” in 2012. They remained friends after the taping and by the end of the year, the pair was hanging out together and their status went from friends to dating. But just as quickly as it began, it was over. After several months together, it was announced that they had gone their separate ways.

"Ryan Gosling pf"

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Sandra Bullock and Ryan Gosling

One thing about Sandra Bullock is apparently she’ll give any guy a shot. She started dating co-star Ryan Gosling back in 2002 after meeting him on the set of “Murder By Numbers.” Even though he was 16 years her junior, the pair found enough in common with each other to be together for a full year. Leaving the relationship broken-hearted, “The Blind Side” actress married reality show star Jesse James and then later divorced him after she and the world found out he was unfaithful.

"Benicio del Toro pf"

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Kimberly Stewart and Benicio del Toro

Who wasn’t shocked when in 2011 Kimberly Stewart announced that she was pregnant with Benicio del Toro’s baby? And it wasn’t just their 13-year age difference that had people’s jaws on the floor, it was the fact that no one knew they had even been together. The announcement was made well after the relationship was over. Stewart gave birth to her daughter in 2011, making her rocker father Rod Stewart a granddaddy for the first time.

"Tom Cruise pf"

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Tom Cruise and Cher

In perhaps one of the most unlikely and oddest celebrity couples ever, Tom Cruise and Cher dated for a brief time back in the 80’s. They were romantically linked in 1987 during the start of his career and at the height of hers. The “If I Could Turn Back Time” singer was 16 years older than Cruise and has said even though he was shy, she told “Glamour” magazine, “I was crazy about him.”

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  • Jayda Brown

    What about Sandra Bullock and Jesse James that was the one that had everyone scratching their heads.

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  • Hope Floats

    WHAT IN THE WORLD WOULD A 23 YEAR OLD BE INTERESTED IN A 16 YEAR OLD FOR?? That’s called pedophilia. But I guess if a celebrity casually admits to a crime then it doesn’t count does it?

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