19 Celeb Couples That Were So, So, So Random, They Almost Broke People's Brains

We didn't see any of these coming.

Some celebrity couples make perfect sense. Blake Lively and Ryan Reynolds? Yep. Sure. Wouldn't dream of arguing with that. But some others? Bizarre as hell.

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Like the rumors that Timothée Chalamet and Kylie Jenner are hooking up. If you think that's a weird pair, hold on to your butts.

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Lets go through some of the strangest celebrity pairings of all time...

1. 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

It's a damn strange pairing, but Chelsea regularly calls 50 one of her favorite exes. Though they only dated for two months in 2010, she says he was "a sweetheart" and "fun to be around." “My friends loved hanging out with him. I loved hanging out with him. It was a pretty short-lived romance," she told ET Canada.

2. Matthew Morrison and Kristen Bell

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Long before Glee and Veronica Mars, these two budding actors went to college together. She told Us Magazine in 2010: "We actually dated very briefly, so I'll have to say maybe Matt Morrison is my favorite part of Glee for various reasons."

3. Ashley Olsen and Lance Armstrong

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Back in 2007, she was 21, he was 36. They reportedly dated for six months, and were seen making out in an NYC bar. Apparently, as we later found out in a tell-all book written about Lance, he was warned by friends to stay away from her, as she'd be a bad influence that could damage his charity work.

4. Kat Dennings and Josh Groban

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You really wouldn't think that these two had absolutely anything in common, but apparently, they were like two peas in a pod. He told Ellen Degeneres that it was really their geek status that brought them together: “Humor is such a huge thing for me, so, you know, the fact that we could talk about Monty Python... I was like, ‘Okay, yeah, we’re on the same page.'" They dated for two years and split in 2016.

5. Tom Cruise and Cher

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I simply cannot imagine what these two talked about, but Tom Cruise and Cher — who is 16 years his senior — had a short fling in the 1980s after meeting at Madonna and Sean Penn's wedding. Cher later told Oprah that she was "crazy for him," and it could have been a "great big romance," but their schedules inevitably got in the way. 

6. Jennifer Lawrence and Chris Martin

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The kooky actress and Coldplay frontman isn't a pairing that we could have seen coming, but that didn't stop them from hooking up on and off for about a year following his "uncoupling" from Gwyneth Paltrow. Jen and Chris officially split in 2015, according to People, mostly because of schedule conflicts.

7. Madonna and Tupac

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The pair were introduced by mutual friend Rosie Perez at the 1993 Soul Train Awards, and ended up dating in secret for two years. It wasn't until 2015 that Madonna opened up about the relationship in an interview with Howard Stern. In 2018, the singer teased an unreleased track that the pair collaborated on, but she's never released it. 

8. Jared Leto and Cameron Diaz

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These two seem worlds apart nowadays, but would you believe that they dated for four long years, starting back in 1999? The pair kept it low-key, to the point where the Telegraph called them one of “Hollywood's most photogenic, but least photographed couples.” After their split in 2003, neither ever commented on the relationship again.

9. Seth MacFarlane and Emilia Clarke

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Yep, the Family Guy creator and Game of Thrones badass dated very quietly from 2012-2013 for about six months. After their split, insiders revealed it was due to location challenges while she was away filming GoT — but she's also spoken about how hard was to have strangers commenting about their relationship right to her face. 

10. Taika Waititi and Rita Ora

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Taika and Rita — who secretly married last year — are an extremely strange couple, you have to admit. But somehow, it seems to work very well. The Kiwi director and the British singer first met in 2018 and started dating sometime between then and early 2021.

11. Jennifer Lopez and Ben Affleck (version 2.0)

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Following J.Lo's split from her fiancé Alex Rodriguez in 2021, never in our wildest dreams did we think she'd do a 180º and start dating her old fiancé, Ben Affleck, again. And then, when she married him? And changed her name to Jennifer Affleck? I'm still in shock. 

12. Simon Cowell and Carmen Electra

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Did we all collectively agree to never speak about this? The British X Factor judge dated supermodel Carmen Electra for a couple of months in 2012 — but she ended things after catching him in bed with another woman.

13. Mark Ronson and Rashida Jones

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Um, what? These two were ENGAGED and dated for many years, which seems like a very bizarre pairing. He proposed to her back in 2003 with a custom crossword puzzle, but they split about a year later. Everything ended on good terms, though; Rashida interviewed Mark for Interview magazine in 2019.

14. Naya Rivera and David Spade

Fred Lee / ABC, Kevin Mazur

The late Glee actress had a short but public fling with David Spade in 2017, which was revealed when the pair were photographed making out by a pool while on vacation together in Hawaii. They hung out with Adam Sandler, Rob Schneider, and their families — it's unclear whether it was just a holiday romance or something more.

15. Taylor Swift and Tom Hiddleston

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It may have only been a flash-in-the-pan summer romance, but these two made headlines for a few months with their world tour through Europe and Australia. Now, we know it was more of a rebound situation (following Taylor's split from Calvin Harris), but it was still a bizarro pairing. Never forget the I <3 T.S. shirt. 

16. Olivia Wilde and Harry Styles

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This one is still fresh in our memories, and maybe we're a bit desensitized to this pairing now — but let's not forget how much the Olivia and Harry pairing threw us for a loop back in 2021. As we know, they met on the set of her film Don't Worry Darling, and were together for nearly two years. 

17. Zach Braff and Florence Pugh

David M. Benett / Max Cisotti/Dave Benett / WireImage

Speaking of Don't Worry Darling cast members, we as a society seem to have quickly moved on from the odd pairing of Zach Braff and Florence Pugh. They faced a ton of backlash thanks to their 20-year age difference, but that didn't stop them from lasting three long years. They split in 2022. 

18. Meghan and Harry

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Again, we're totally used to this couple by now. But please cast your mind back to 2016, when we first read headlines that the eligible bachelor Prince Harry was dating the B-list Canadian Suits actress. I would bet a million dollars that no one saw that coming. 

19. And finally, Kanye and Julia Fox

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Looking back, it kinda makes perfect sense. But when Ye and Julia Fox started getting photographed around Manhattan together, we were collectively shocked by the pairing. It only lasted a month, but the photos and outfits that they gave us will live on forever. 

Any other celebrity pairings that completely blow your mind? Let us know in the comments!