Celebrities Who Dated the Same Person Will Blow Your Pop Culture-Lovin' Mind

Hollywood is a small town, especially when it comes to the love lives of the rich and famous. It's amazing to see how many celebrities have dated the exes of others — it's basically guaranteed to happen unless a celeb is actively seeking out a non-famous partner. Since those celebs are few and far between, let's take a look at the surprising celebrities who dated the same people.

Zoe Kravitz

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The Divergent star dated Badgley from 2011 to 2012. Badgley and Lively dated for almost three years and broke up in 2010, despite having to work together for another two years on Gossip Girl.

Jack Antonoff

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Who once upon a time dated…

Scarlett Johansson

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Antonoff, who has been dating Girls creator Dunham for two years, took Johansson to her senior prom.

Cameron Diaz

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Diaz is allegedly dating…

Benji Madden

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Who used to go out with…

Paris Hilton

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Yep! Madden and Hilton used to date when Hilton’s then-BFF, Nicole Richie, first started seeing her current partner, Madden’s identical twin Joel Madden. Hilton and Madden started, and finished, dating in 2008. Madden began dating Diaz in spring 2014. Guess he likes blondes!

Ian Somerhalder

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Who dated this Lost alum back in the day…

Maggie Grace

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Grace and Somerhalder met on the set of Lost in 2006 and dated for a year. Somerhalder and Dobrev play love interests on The Vampire Diaries but broke up in 2013 after three years of dating. Despite the breakups, both Grace and Dobrev appear to get along well with their now-ex Somerhalder.

Dianna Agron

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The Glee star used to date…

Alex Pettyfer

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The I Am Number Four star also stepped out with…

Emma Roberts

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The American Horror Story star began dating Pettyfer in 2007. The couple broke up a year later after Pettyfer got Roberts’ first name tattooed on his finger. (Oops.) Pettyfer started dating his I Am Number Four co-star, Agron, in 2010. The couple split after a year.

Reese Witherspoon

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Witherspoon dated…

Jake Gyllenhaal

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Who became the subject of a song written by ex-girlfriend…

Taylor Swift

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It’s always so odd to me that Witherspoon and Swift share a love connection, but both women were allegedly pretty serious about the Prince of Persia. Witherspoon dated Gyllenhaal for nearly three years before the pair called it quits in 2009. Swift and Gyllenhaal allegedly dated in 2010 and split up just around the holidays. Gyllenhaal is the suspected inspiration behind the song “State of Grace” on Swift’s album Red.

Lucy Hale

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The Pretty Little Liars star used to date this HBO star…

Chris Zylka

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The current star of The Leftovers also dated his Secret Circle co-star.

Phoebe Tonkin

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And, apparently, things didn’t end very well with either of them. Zylka and Hale dated for six months before breaking up in 2012. The world knew about their breakup immediately because a super bitter Zylka tweeted that he “didn’t have a girlfriend anymore” and that she decided that she was “too good.” Tonkin, who Zylka dated in 2013, posted an Instagram of a destroyed version of one of Zylka’s paintings with the caption “That felt good.” Ouch.

Angelina Jolie

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Before she ever met Brad Pitt, Jolie was married to…

Billy Bob Thornton

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The Fargo star was previously engaged to…

Laura Dern

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How’s this for awkward? Dern and Thornton were engaged to be married in 2000. Then Dern went to work on a film — and her fiancé married Jolie. Jolie and Thornton’s marriage ended in 2003.

Nick Cannon

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Before this reality star was a "brand," she dated this actor...

Kim Kardashian

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And that wasn’t the only Nick she dated. Kardashian also briefly dated…

Nick Lachey

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Lachey and Kardashian went on a few dates back in 2006 when she was known as being nothing more than Paris Hilton’s club pal. Lachey has accused Kardashian of using him for fame, hinting to the press that Kardashian called the paparazzi while out with him. Cannon and Kardashian dated for a few months in late 2006 but broke up in 2007, allegedly because Cannon didn’t like that she lied to him about her sex tape.