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

LAS VEGAS - NOVEMBER 07: Paris Hilton and Good Charlotte guitarist Benji Madden appear at the after party for a special screening of the Lionsgate film, 'Repo! The Genetic Opera' at Prive Las Vegas inside the Planet Hollywood Resort & Casino during the early morning on November 7, 2008 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
Source: Ethan Miller/Getty Images Entertainment/Getty Images

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.

Blake Lively

Dated…

Penn Badgley

Who also dated…

Zoe Kravitz

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.

Lena Dunham

Currently dates…

Jack Antonoff

Who once upon a time dated…

Scarlett Johansson

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

Cameron Diaz

Diaz is allegedly dating…

Benji Madden

Who used to go out with…

Paris Hilton

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!

Nina Dobrev

Used to date…

Ian Somerhalder

Who dated this Lost alum back in the day…

Maggie Grace

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

The Glee star used to date…

Alex Pettyfer

The I Am Number Four star also stepped out with…

Emma Roberts

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

Witherspoon dated…

Jake Gyllenhaal

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

Taylor Swift

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 PersiaWitherspoon 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

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

Chris Zylka

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

Phoebe Tonkin

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

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

Billy Bob Thornton

The Fargo star was previously engaged to…

Laura Dern

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

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

Kim Kardashian

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

Nick Lachey

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.