Jennifer Aniston’s Dating History: From Brad Pitt and John Mayer to Justin Theroux and More

Charlie Schlatter

Esquire reported that Jennifer and her Ferris Bueller costar “had a brief, torrid romance” while filming the TV show in 1990.

Daniel McDonald

“He was my first love,” Jen has said of her 1990 to 1995 romance with the actor, who died at 46 in 2007. “He would have been the one. But I was 25, and I was stupid.”

After Daniel’s tragic death, Daily Mail reported that Jennifer was “heartbroken.”

Adam Duritz

She briefly dated the Counting Crows frontman in 1995 — and her longtime costar and BFF Courteney Cox was linked to him the next year!

Tate Donovan

She dated the actor— who was pal Sandra Bullock’s ex — in 1995. After briefly getting engaged, they ended things in 1998, right around the time he was cast as her love interest on Friends. 

“The people that know that we dated think that we met on Friends,” Tate admitted in 2023. “But in fact we had dated for two years before then, and it was over by the time we were on Friends together.”

Brad Pitt

Brad and Jennifer’s relationship was extremely publicized from right when they met in 1998. After two years of dating, they tied the knot in 2000. However, they announced their separation in January 2005 and finalized the divorce later that year. 

The split was the subject of a media frenzy, as Brad was accused of cheating on Jen with his Mr. and Mrs. Smith costar Angelina Jolie. In a 2015 interview, Jennifer insisted, “Nobody did anything wrong. It was just like, sometimes things [happen].” She has also shut down reports that the pair split because she didn’t want to have kids. 

In 2020, the exes proved they were on friendly terms when they had an amicable reunion at the SAG Awards.

Vince Vaughn

“I call Vince my defibrillator. He brought me back to life [after my divorce],” she’s said of her rebound with the actor, who was in Mr. & Mrs. Smith. The two started dating while filming The Break-Up in 2005 but ended their relationship by December 2006.

John Mayer

Was Jen the one that got away? “I’ve never really gotten over it,” the musician and infamous Hollywood player once said of their 2009 split after a year together.

John faced major backlash for an interview he did with Playboy after the split where he hinted that Jennifer, who is nine years his senior, was too old for him. “I’ll always be sorry that it didn’t last,” he said. “In some ways I wish I could be with her. But I can’t change the fact that I need to be 32.”

Justin Theroux

After eight years together — three of which they were married — Jen and the actor, 52, called it quits in 2018. However, they remain close and still spend time together with mutual friends.