15 Celebrity Couples That Were So Unexpected They Still Keep Me Up At Night

Here we go!

When it comes to Hollywood pairings, I don't get surprised by who ends up with who too often. But when it comes to the following couples/former flames, my face always ends up like this:

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1. Olivia Wilde and Harry Styles

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Fans literally had to do a double take when they noticed Olivia and Harry walking hand in hand during a January 2021 wedding. The couple is still going strong — most recently, the Booksmart director was seen supporting the former One Direction member at his Harryween concert, dressed as Dolly Parton.

2. Pink and Joey Fatone

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According to the former NSYNC member, "We went out. We were cool as heck. But I guess I wasn't her type."

3. Chelsea Handler and 50 Cent

Chelsea Handler @chelseahandler

Special shout out to my favorite ex @50cent (and the only ex-boyfriend I am still asked about in every interview) who gets an extra special shout out in my @hbomax special. Now, everyone will know that you’re one big fat teddybear. Xx

05:13 PM - 21 Aug 2020

Twitter: @chelseahandler

The hip-hop mogul dated the comedian for a few months in 2010. Chelsea still refers to 50 Cent as her "favorite ex."

4. Cher and Tom Cruise

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The famed actor and iconic musician had a fling in the 1980s. In 2013, Cher told Andy Cohen that Tom was one of her "top-five" favorite lovers ever.

5. Ashley Olsen and Lance Armstrong

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The business mogul and former professional cyclist had a budding romance back in 2007, but Lance's friends urged him to end things with Ashley because of their 15-year age gap.

6. Michelle Rodriguez and Zac Efron

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While their PDA-filled Ibiza trip had everyone talking back in 2014, the Fast & Furious star only dated the Disney vet for two months.

7. Madonna and Dennis Rodman

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Their high-profile 1994 romance only lasted two months, but whew chile, it was nothing short of a roller coaster ride.

8. Fergie and Justin Timberlake

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According to Fergie, she had a fling with a young JT while she and her band Wild Orchid were on tour with NSYNC back in the late '90s. The relationship was definitely inappropriate and probably illegal, as Fergie revealed that Justin was only 16 and she was 23.

9. Bella Thorne and Scott Disick

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Let's be real — outside of Kourtney Kardashian, most of Scott's dating history is shocking, but his relationship with Bella really had me like, "Wait, what?!" Their short romance took place during the spring and summer of 2017.

10. Naya Rivera and David Spade

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The late Glee star and comedian had a spring romance back in 2017. Onlookers were taken by surprise when they first spotted the two making out at the Halekulani Hotel pool in Waikiki, Hawaii.

11. Nicole Kidman and Lenny Kravitz

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Believe it or not, Lenny was Nicole's landlord when they first started dating in 2002. The two later got engaged. As for why they never got married, Nicole said, "I wasn’t ready. We weren’t ready. … I get engaged and I get married — that’s my thing. I don’t want to date. I’m interested in a very, very deep connection.”

12. Carmen Electra and Simon Cowell

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After meeting on the set of Britain's Got Talent, Carmen and Simon dated for nearly six months. Unfortunately, their relationship quickly came to an end when the former Baywatch star walked in on Simon in bed with Lauren Silverman in 2013. Simon is still dating Lauren, and they currently have two children together.

13. Brigitte Nielsen and Flavor Flav

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Their love unfolded after meeting in 2004 on VH1's The Surreal Life. Their connection was so strong that the two ended up getting a spin-off show called Strange Love in 2005. But Brigitte and the Public Enemy co-founder called it quits by the end of the show due to their constant disagreements.

14. Grimes and Elon Musk

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After dating for a few weeks, Grimes and Elon took their relationship public when they attended the 2018 Met Gala together. In 2020, the couple welcomed a baby boy into the world. But after three years together, they called it quits.

15. Lastly, Madonna and Tupac

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Rumors swirled in the 1990s about a steamy relationship brewing between the two iconic musicians, and during a 2015 interview with Howard Stern, Madonna officially confirmed they dated. “I was dating Tupac Shakur at the time, and the thing is he got me all riled up on life in general,” she said. “So, when I went on the show, I was feeling very gangsta.” A handwritten letter from Tupac to Madonna dated back to 1995 was later released, which gave a little more perspective on their relationship.

Is there a celebrity couple that still blows your mind? Tell me about them in the comments below!