Did They Really Date?!

This blog is about surprising past celebrity couples that make you think WHAT! From Brad Pitt and Christina Applegate to Tyra Banks and Seal!

Did They Really Date?!

Ashton Kutcher & January Jones

He may be dating Mila Kunis now, but at one point Ashton Kutcher was mad aboutMad Men actress January Jones. The two stars (who dated from 1998 to 2001) were both models before Kutcher got his big acting break playing Michael Kelso on That ’70s Show. But he doubted his girlfriend’s ability to make a similar leap. “He was like, ‘I don’t think you’re going to be good at this.'” Jones told GQ in 2009. “So, f*ck you! He only has nice things to say now — if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.”

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Danielle Fishel & Lance Bass

You might be surprised to know that in the heyday of Lance Bass‘ ‘NSYNC superstardom, he dated none other thanDanielle Fishel also known as Topanga fromBoy Meets World! The actress recently posted on Twitter a picture of the two of them at her senior prom: “Pics or it didn’t happen!” This was, of course, years before the pop singer came out of the closet and admitted that he was gay. Fishel is nowengaged and the actress will soon return to the small screen in Girls Meets Worldplaying Topanga as a mom!

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Sandra Bullock & Matthew McConaughey

There’s no denying that Matthew McConaughey is a Hollywood hottie —especially when he’s shirtless! But we have to admit, it’s a little surprising that he managed to snag Sandra Bullock while rocking those leather pants and that mustache. The lovebirds met while filmingA Time to Kill in 1996, and sparks flew immediately. “I just look at her and I think, Wow!” McConaughey told In Style. “But she doesn’t know how beautiful she is or how much people like her.” The magic dwindled a few years later, but the pair remained friends. “I feel very cared for by Matthew,” Bullock told Cosmopolitan in 2003. “No matter where he is in his life or where I am in mine — he could be married — I know we would stay close.” We hope that’s cool with his new wife Camila Alves!

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Seal & Tyra Banks

Seal is most famous for his (failed) marriage to Heidi Klum — but before he landed the German beauty, he canoodled with another sexy supermodel. The “Kissed by a Rose” singer dated Tyra Banks (who’s 10 years his junior) for a few months in 1996.

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Scarlett Johansson & Sean Penn

Chalk it up to their staggering age difference, but Scarlett Johansson and Sean Penn’s brief fling seemed to catch everyone off guard. The unlikely duo developed a casual relationship in 2011 — shortly after Johansson’s three-year marriage with Ryan Reynolds ended in divorce. News of their romance quickly dominated headlines, and the actress, who is 25 years Penn’s junior, was unprepared for the media attention. “In my marriage, funnily enough, we had relative privacy,” she told Vogue in April. The scrutiny she received with Penn “was a little bit of an adjustment,” she said. The pair survived only a few dates before calling it quits.

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Brad Pitt & Christina Applegate

Brad Pitt is best-known for romancing two of Hollywood’s most famous ladies: ex-wifeJennifer Aniston and current fianceeAngelina Jolie. But in the early ’80s the actor dated a slew of other famous beauties, one of whom was actressChristina Applegate. “We went to the MTV Awards [in 1989] and I ditched him!”says Applegate, who was starring on the hit show Married with Children at the time. “I left him there and I felt really bad about it, I really, really do. I left with somebody else.” What was she thinking?

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Sarah Jessica Parker & Michael J. Fox

Sarah Jessica Parker and Michael J. Foxreportedly got together in 1986 — one year after his hit Back to the Future and her movie Girls Just Wanna Have Fun hit theaters. He escorted her to the Jewish National Funds Annual Tree of Life Awards in December (pictured), but their brief fling didn’t last.

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Rihanna & Shia LaBeouf

Anyone who’s seen Rihanna in concert knows that the singer is skilled at turning up the heat. But there is one person who wasn’t transfixed by her sex appeal. After hitting the town with RiRi in 2007, Shia LaBeoufquickly relegated her to the friend zone. “It never got beyond one date,” the actor toldPlayboy in 2009. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”

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Drew Barrymore & Christian Bale

He must have done something wrong because Drew Barrymore ditched Christian Bale after only one date! The two former child stars linked up when they were teenagers. “We went to see some bloody awful horror film, and that was the end of it,” Bale told GQ Australia magazine in 2012. “She never called again.” The actor may have been heartbroken at the time, but he went on to marry (and have a child with)Sibi Blazic. Barrymore is currently expecting her first child with husband Will Kopelman.

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Nick Lachey & Kim Kardashian

Considering that Nick Lachey isn’t a professional athlete or a rapper, it’s pretty shocking that he was able to woo Kim Kardashian! After Lachey parted ways with ex-wife Jessica Simpson, he started up a fling with Kardashian (who was a relatively unknown stylist at the time). “They’re sweet on each other,” a source told People in 2006. “It’s the beginning stages of a relationship.” They soon parted ways, and Kim went on to date a slew of other celebs — including ex-husband Kris Humphriesand current beau Kanye West. Nick, on the other hand, just welcomed his first child with wife Vanessa Lachey.

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Chelsea Handler & 50 Cent

When rumors first started that Chelsea Handler was dating rapper 50 Cent, the pair claimed they were just friends. The funny lady fueled the fire by tweeting a photo of them kissing in bed in December 2010. “I don’t know why anyone thinks I would ever date a rapper,” she captioned the pic. But it proved to be more than just a playful hookup. “We dated for a couple months and then we had a falling out,” Handler toldHoward Stern in January — but at least their relationship provided some laughs. “I thought it was kind of amusing that I would even be with 50 Cent,” she added. “I thought it was funny.”

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Lisa Kudrow & Conan O’Brien

If you were a big fan of Phoebe Buffay onFriends, you actually have Conan O’Brien to thank for those years of laughs. Lisa Kudrow says she may not have stuck it out in comedy if it weren’t for the encouragement that the late-night funnyman gave her on an early date. “He was really smart, really funny and he thought I was funny,” Kudrow told Moremagazine in 2011. The two dated briefly, but decided they were “better as friends.” Kudrow went on to pursue her comedy dreams with vigor, eventually landing the iconic role as the goofy guitar player.

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Tom Cruise & Cher

Long before Katie Holmes or Nicole Kidman, Tom Cruise strangely spent some quality time with Cher. Despite the 16-year age gap, the two met in the ’80s and hit it off. “I was so crazy about him,” Cher told Oprah Winfrey in 2008. Cruise had just wrapped up his first major role in Risky Business, while the more established Cher was celebrating a career of hit singles and movie roles. “He was a shy boy. He didn’t have any money,” recounted Cher. “One night we walked into this restaurant in New York and this girl came up, this waitress came up and she took our order and stuff like that and he said, ‘I knew that girl in school and she wouldn’t give me the time of day.'” The iconic pop star even revealed that she “lived in his apartment.” Sounds serious!

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