Jennifer Aniston starred as the beloved Rachel Green on Friends and has always been known as one half of the iconic Ross and Rachel pairing. Despite their on-screen romance and a small crush off-screen, their romance never became a reality. Behind the scenes, Aniston had a few memorable relationships and a couple of short-lived ones. We’ve rounded up each of the actress’s romances, whether they spanned months or years, so take a glimpse into the love life of Jennifer Aniston.
Charlie Schlatter
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Aniston had a brief romance with her Ferris Bueller sitcom co-star, Charlie Schlatter, in 1990. Schlatter portrayed Ferris in the short-lived series, while Aniston portrayed his older sister Jeannie. The two were only together for a short while, but the sitcom was canceled halfway through its first season.
Daniel McDonald
After her relationship with Schlatter came to an end, Aniston moved on with actor Daniel McDonald. The two remained together for five years, just as she was beginning to star on Friends. Aniston and McDonald eventually ended things in 1995, and sadly, McDonald passed away from brain cancer in 2007.
“He was my first love—five years we were together,” Aniston shared in 2015. “He would have been the one. But I was 25, and I was stupid.”
Adam Duritz
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The actress also dated Adam Duritz of Counting Crows for a short time in 1995 after meeting at The Viper Room nightclub. But their relationship was based on a little white lie by Duritz’s friends.
“A bunch of my friends lied to me and told me she had a crush on me,” Duritz shared. “Those same friends lied to her and told her I had a crush on her. I honestly had no idea who she was, I had been on the road during all of Friends. I had never seen it, I don’t think.”
Duritz added, “[She was] really nice, really funny, really pretty… And also, she liked me.”
Tate Donovan
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That same year after her time with Duritz, Aniston met actor Tate Donovan through a mutual friend. Donovan shared that he didn’t know who Aniston was when they met, but it wasn’t long before they began dating.
Aniston and Donovan remained a couple for two years, from 1996 to 1998, and even moved in together. But soon their relationship became rocky, making things awkward when Donovan was cast as a guest star on Friends.
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“I had mentioned to the producers that it’s always hilarious when Jen, who’s this gorgeous woman, is madly in love with somebody and the guy just doesn’t see it,” Donovan shared. “And so, the producers came to me and said, ‘Hey, we want you to do a five-episode arc where you guys are dating and you’re not really that into her.’”
Of course, the two were in the midst of a breakup, but they thought maybe it would go smoother if they had to act together in a professional setting. Unsurprisingly, that was not the case, as both actors said it made the breakup much more painful.
“It was just six episodes,” Donovan explained. “I mean, only because we were breaking up. We were like, ‘Hey, can we not keep doing this? ‘Cause this is really painful and tough.’”
Brad Pitt
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Aniston met her first husband, actor Brad Pitt, in 1994, but it wasn’t for another couple of years that they would start dating. Following her breakup with Donovan in 1998, Aniston went on a date with Pitt. Once they became a couple, the two kept their relationship private, not making any public appearances until September 1999.
Two months later, they announced their engagement and they were married by July 2000. Aniston and Pitt quickly became the It-couple, appearing on red carpets together. In 2001, Pitt made a cameo in a Friends episode, where his character was a member of the “I Hate Rachel Green Club.”
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In 2002, Aniston and Pitt co-founded the production company Plan B Entertainment, which produced films like Troy (2004) and Charlie and the Chocolate Factory (2005). But in 2005, after seven years together, the couple announced their separation.
“We happily remain committed and caring friends with great love and admiration for one another,” the former couple shared in a statement.
Vince Vaughn
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Aniston embarked on a short-lived romance with The Break-Up co-star Vince Vaughn in the summer of 2005. But they never made any official public appearances beyond the premiere of their film.
The couple split up in December 2006, with both staying quiet about the breakup for a while. But Aniston has had nothing but nice things to say about the actor in the years after their breakup.
“He literally brought me back to life,” Aniston shared. “My first gasp of air was a big laugh! It was great.”
John Mayer
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At a 2008 Oscars party, Aniston met her soon-to-be boyfriend, John Mayer. Aniston and Mayer became an item, starting an on-and-off romance. Their relationship didn’t last very long and soon Mayer cleared up the rumors.
“I ended a relationship to be alone, because I don’t want to waste somebody’s time if something’s not right,” Mayer explained.
They briefly reunited in 2009 and attended the Oscars again — this time as a couple — but this rekindling didn’t last long as Aniston and Mayer once more called it quits.
Justin Theroux
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The Friends star met her second husband, Justin Theroux, back in 2007 on the set of Tropic Thunder, where Aniston was visiting Ben Stiller. But it wasn’t until 2010 that they reconnected and sparks began to fly. By 2011, the couple were living together, and two years later, they exchanged vows. Aniston and Theroux’s wedding was a secret that even friends and family weren’t privy to..
In 2018, Aniston and Theroux announced they were separating, explaining that they were better off as best friends, which they have remained ever since.