Jennifer Aniston Has Dated Some of Hollywood’s Hottest Hunks: Her Full Dating History

Charlie Schlatter

From 1990 through 1991, Jennifer costarred with Charlie Schlatter on the Ferris Bueller’s Day Off spinoff TV series. Their relationship wasn’t confirmed until 2014 when the show’s former comedy writer’s assistant, Jim Nelson, revealed he witnessed their “brief” and “torrid” romance to GQ magazine.

Daniel McDonald

Jennifer dated fellow actor Daniel McDonald for five years throughout the 1990s. The actress later called Daniel her “first love” in an interview with the New York Times in January 2015, eight years after Daniel died from brain cancer.  

Adam Durtiz

The Counting Crows band member Adam Duritz dated Jennifer briefly in 1995. After they broke up, he was linked to Jennifer’s close friend Courteney Cox.

Tate Donovan

Before landing a brief role on Friends, Tate Donovan dated Jennifer for three years after they met in 1995. The actor later opened up about their split over a decade later, which occurred while he appeared on the sitcom. “That was tricky to sort of act, and act like we are just meeting each other, and falling in love, or whatever, interested in each other, when we’re sort of breaking up,” he told Us Weekly in September 2018. “That was just tough.”

Jon Stewart

The Daily Show alum Jon Stewart confirmed he had asked Jennifer out on a date sometime in the late 1990s while she appeared on his show in August 2010. “I remember you brought so many of your friends,” the comedian recalled. “And I remember thinking, ‘She’s so excited to be on a date with me, she wants me to get to know her posse.’”

Paul Rudd

Another Friends costar in the mix! Jennifer and Paul Rudd were rumored to be in love for several years throughout the late 1990s and early 2000s. Jennifer confirmed they dated while they were young. They starred in multiple films together, including the 1998 movies The Object of My Affection and The Newton Boys. They reunited onscreen again in 2012 for Wanderlust.

Brad Pitt

Brad Pitt was linked to Jennifer in 1998, later marrying her in 2000. Five years later, the famous lovebirds announced their split amid Brad’s new romance with Angelina Jolie. However, he and Angelina emphasized at the time they didn’t start dating until after he and Jennifer divorced.

Brad and Jennifer now remain friendly, as they were seen smiling and holding hands at the 2020 SAG Awards.

Vince Vaughn

After her divorce from Brad Pitt, Jennifer moved on with future The Break-Up costar Vince Vaughn. However, their romance was short-lived as they confirmed their split in December 2006. The Freaky actor cited heavy media attention as the cause of their breakup.

Paul Sculfor

Although they weren’t in a serious relationship, British model Paul Sculfor and Jennifer casually dated throughout 2007.

John Mayer

From April 2008, Jenifer and singer John Mayer had an on and off relationship until their breakup in March 2009.

Bradley Cooper

After landing their roles in He’s Just Not That Into You, Bradley Cooper briefly dated Jennifer throughout the summer of 2009. Although their relationship didn’t last long, they remained friends.

Gerard Butler

Jennifer and actor Gerard Butler sparked dating rumors after costarring in The Bounty Hunter in 2010, but never confirmed the romance.

Justin Theroux

Although they met in 2007 while filming Tropic Thunder, Jennifer and Justin Theroux didn’t begin a relationship until after reuniting for Wanderlust in 2010. They became engaged in August 2012 and married three years later. However, Jennifer and Justin called it quits in February 2018. The duo remained friendly following their divorce later that year.