The course of true love never did run smooth… at least, according to William Shakespeare. The Bard knew what he was talking about, too. It doesn’t matter who you are: when it comes to love and dating, everybody out there has a rocky road ahead of them on the path to finding lasting love.

The heart doesn’t discriminate—it wants what it wants, after all—and that’s true no matter who you are. It doesn’t matter if you’re a celebrity or an average Joe; you fall for the people you fall for and there’s no controlling it.

Of course, sometimes the people you fall for make more sense than others. When you see who these celebrities dated back in the day, you’ll totally understand just how strange love can be…

1. Natalie Portman and Moby: While they might sound like the ultimate odd couple, believe it or not, actress Natalie Portman (known for films such as Stars Wars and Black Swan) dated the electronic musician Moby for a few months in 2001. He has said that he faced “nerd wrath” from her fans for being her boyfriend even briefly.

2. Paris Hilton and Benji Madden: Back in 2008, Paris Hilton, the original socialite famous just for being famous, briefly dated Good Charlotte frontman Benji Madden. Their relationship only lasted a couple of months, though Paris’s Simple Life co-star Nicole Ritchie is still married to Benji’s brother and bandmate, Joel.


3. Aubrey Plaza and Michael Cera: This couple flew so far underneath the radar that no one even knew they were dating! Aubrey Plaza revealed in a podcast interview that she dated actor Michael Cera for a year-and-a-half after they met on the set of Scott Pilgrim Vs. The World.

4. Sandra Bullock and Ryan Gosling: While filming the movie Murder By Numbers, Ryan Gosling and Sandra Bullock fell in love. They pair dated seriously for a couple of years back in the early aughts. Rumor has it that their 16-year age difference played a role in their split.


5. Lizzie Caplan and Matthew Perry: You might not have known that Matthew Perry of Friends and Lizzie Caplan of Masters of Sex were a serious couple for years, but they totally were! They were also an unlikely—but adorable—pair. Sadly, they are no more, having split in 2012.

6. Fergie and Justin Timberlake: Justin Timberlake has never spoken up about their brief courtship, but singer Fergie of the Black Eyed Peas did reveal that the couple dated, though their relationship was never meant to be anything serious. “He was my Mr. Right Now,” she famously said.

7. Scarlett Johansson and Jack Antonoff: Musician Jack Antonoff is currently dating Lena Dunham, the creator of the HBO series Girls. However, back in the day, he squired Scarlett Johansson around town on his arm. In fact, the two even went to his senior prom together! Clearly he was the envy of every dude at school.


8. Blake Lively and Leonardo DiCaprio: In 2011, Leonardo DiCaprio took a break from being a notorious ladies man to date Gossip Girl star Blake Lively. The pair did everything they could to keep their secret meetings private, but the paparazzi found them, even when they were on Leo’s private yacht!

9. Rihanna and Shia LeBeouf: In 2007 when Shia LeBeouf’s star was on the rise, the young actor went out on a date with singer Rihanna. Tragically, according to Shia, they never even got to date number two. “The spark just wasn’t there,” he reported.


10. January Jones and Ashton Kutcher: Way before she starred as Betty Draper on Mad Men, January Jones was just an aspiring actress who was dating TV star Ashton Kutcher. The couple were together for a few years before they inevitably wound up going their separate ways.

11. Rashida Jones and Mark Ronson: In 2003, Rashida Jones and musician Mark Ronson dated so seriously that they even got engaged! They wound up splitting the next year. “We were too young to be engaged and we both were very nervous about it,” Rashida revealed years later.

12. Alanis Morrisette and Ryan Reynolds: These two might sound like an unusual couple, but at least they had their Canadian roots in common. The couple dated and then became engaged in 2004, though they called it off just three years later.


13. Renee Zellweger and Bradley Cooper: This pair seemed like they were perfectly matched in some ways. Though the couple dated for a couple of years after meeting in 2011, their love just wasn’t meant to be.

14. Kim Kardashian and Nick Cannon: It’s crazy to think that Mrs. Kanye West and the former Mr. Mariah Carey were ever an item, but in the early 2000s they were the real deal. Apparently when they broke up in 2007, Kim was absolutely heartbroken. Clearly, she survived.

15. Reese Witherspoon and Jake Gyllenhaal: These two might both be A-list actors in their own right, but that doesn’t mean that seeing them together won’t leave a person scratching their head. This odd couple dated for two years in the early 2000s before eventually calling it quits.

16. Keira Knightly and Jamie Dornan: Between 2003 and 2005, when Keira Knightly was quickly becoming the new it-girl, she was dating a relatively unknown Irish actor named Jamie Dornan. Yes, that’s Christian Grey himself. He might not have been on everyone’s radar back then, but he was still a total stud.

17. Rosario Dawson and Danny Boyle: The actress and filmmaker seem like a completely baffling pair, but apparently when they dated it was intense and serious. They managed to keep it almost entirely to themselves until they split in 2013. “We dated longer than people think we did,” teased Rosario.


18. Emily Blunt and Michael Bublé: While these two are each happily married to other people, between 2005 and 2008, singer Michael Bublé and actress Emily Blunt were in a very serious relationship… and the Internet has all of the photos to prove it. Sadly, their love was not written in the stars.

19. Ashley Olson and Lance Armstrong: This might be the last couple on the list, but that doesn’t make them any less of a strange match. Back in 2007, Tour de France star Lance Armstrong was suspected to have briefly dated Ashley Olson of Full House fame. What would have ever paired them together?

Did you have any idea that some of these celebrities were ever romantically entangled? It must be true what they say: love really is blind!

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