When it comes to dealing with media attention around one’s love life, no one knows the game better than Jennifer Aniston — which is why, when looking back at the star’s long dating history, it can be difficult to separate fact from fiction. After skyrocketing to fame in the mid-‘90s thanks to Friends, Aniston was basically everywhere — and after her 2005 split from Brad Pitt, who quickly took up with Mr. & Mrs. Smith co-star Angelina Jolie, so were rumors about her love life.
Over her decades-long career, though, Aniston has somehow been able to weather any media storm that tries to rain on her parade, and that includes the often-invasive inquiries about her love life. We love the candor and confidence with which she speaks about her past relationships, and how she’s consistently respectful when discussing someone involved in her personal life.
“My marriages, they’ve been very successful, in [my] personal opinion,” she confessed to Tig Notaro in 2018, referring to exes Brad Pitt and Justin Theroux. “When they came to an end, it was a choice that was made because we chose to be happy.”
After all these years, we’re still really interested in learning more about how one of Hollywood’s biggest stars can balance her work, star persona, and personal life. We’re going as far back as we can with Aniston’s romantic life, looking back at her past relationships and the chapters that defined those moments. Take a look through this slideshow to learn more about Jennifer Aniston’s past relationships, from Tate Donovan to her marriage to Justin Theroux.
A version of this article was originally posted on Aug 2021.
Tate Donovan
Jennifer Aniston’s first major high-profile relationship was with actor Tate Donovan. The couple started dating in 1995, around the time that Aniston’s star was on the rise thanks to a little show called Friends. The two dated for about three years before going their separate ways in 1998.
While their split was fairly amicable, it wasn’t any less tough. For starters, the actors were two of the ’90s biggest stars. Not to mention, Donovan landed a role on Friends where he played Aniston’s love interest.
“It was just six episodes. 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,'” Donovan told Us Weekly in 2018. “The people that know that we dated think that we met on Friends. 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
Following her three-year relationship with Donovan, Aniston began dating Brad Pitt. The iconic couple’s romance began in 1998, and they dated for roughly two years until their wedding in 2000. The couple was a constant media fixation, and things didn’t get better in the mid-aughts when Pitt starred alongsideAngelina Jolie in the film Mr. & Mrs. Smith.
Aniston and Pitt announced their split in early 2005, and finalized their divorce in October of that year. In the immediate time following, scrutiny on Pitt and Jolie’s relationship only increased. But the couple was able to weather the media storm until they ultimately split in 2016, after more than a decade and six children together.
As for Pitt and Aniston, the two have seemingly gotten to a better place in their post-divorce relationship. In 2020, they worked together on a virtual table read of the film Fast Times at Ridgemont High, and appeared to be really supportive of one another at the Screen Actors Guild Awards in 2020.
Aniston, herself, even reflected on her relationship with Pitt back in 2015. “We’re not in daily communication,” she told The Hollywood Reporter. “But we wish nothing but wonderful things for each other. Nobody did anything wrong. You know what I mean? It was just like, sometimes things [happen].”
Vince Vaughn
After her very public divorce from Pitt, Aniston began spending a lot of time with her Break-Up co-star Vince Vaughn. The relationship was fairly short-lived, unfortunately. Due to the media scrutiny focused on Aniston after her split from Pitt, the circumstances of the relationship just couldn’t outlast the constant paparazzi.
“For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it,” he told Playboy Magazine in 2015, per Us Weekly. “You like someone and you’re spending time with them; that’s separate and that was all fine. But I really spent most of that time finding ways not to be drawn into the attention.”
John Mayer
We’re going to be honest here. This relationship really caught us off guard. Between 2008 and 2009, Aniston was in an on-again, off-again relationship with singer John Mayer. Their most notable public appearance came at the 81st annual Academy Awards, pictured above. After their breakup, though, Mayer made some *choice* statements about Aniston, who is eight years his senior.
“I’ll always be sorry that it didn’t last,” he told Playboy after the breakup, per Marie Claire. “In some ways I wish I could be with her. But I can’t change the fact that I need to be 32…One of the most significant differences between us was that I was tweeting. There was a rumour that I had been dumped because I was tweeting too much. That wasn’t it, but that was a big difference.”
Aniston, however, still saw Mayer as a “wonderful guy,” according to the outlet. “We care about each other. It’s funny when you hit a place in a relationship and you both realise, we maybe need to do something else, but you still really, really love each other. It’s painful,” she told Vogue, per Marie Claire.
Justin Theroux
Jennifer Aniston’s relationship with Justin Theroux actually goes way back. The two first met in 2007, when mutual friend Ben Stiller introduced them. But they didn’t start dating until three years later in 2010, while working on the film Wanderlust.
Two years later, in August 2012, Aniston and Theroux announced their engagment and tied the knot in 2015. Sadly, though, the couple’s romance came to an end when they made the decision to split in 2018. But Aniston and Theroux have seemingly remained incredibly supportive of one another.
During their marriage, however, even Theroux admitted that there were some challenges to being married to Aniston — most of which were created by the scrutiny around her. “In ideal circumstances, you’re known for what you do, or for the contributions you make in the arts, literature, movies, whatever. Even if it’s a negative review, OK — that’s fair play,” he told Rolling Stone in April 2021. “But there are people who are only curious about the private lives of other people, and… I think the best thing to do is to train your eyes away from it.”
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