Jennifer Aniston’s Romantic History: Every Star She’s Dated, Married, & Divorced

From her marriage to Brad Pitt, to her brief fling with Bradley Cooper, we’re looking back at ‘Friends’ star Jennifer Aniston’s complete dating history.

Jennifer Aniston‘s love life has dominated news headlines for over two decades, and she’s been linked to plenty of fellow A-listers through the years. The 51-year-old was famously married to Brad Pitt, 56, in the early 2000s and the pair recently reunited for a virtual reading of Fast Times At Ridgemont High. The Hollywood mainstay also dated the likes of John Mayer and Vince Vaughn, but we’d bet there’s few people you didn’t know Jen was linked to. Read on to find out who!

Charlie Schlatter

Before she hit the big time as Rachel on Friends, Jen was cast in the short lived TV adaptation of the John Hughes film Ferris Bueller’s Day Off, in 1990. Former writer on the show, Jim Nelson, revealed 24 years later that she had dated her co-star Charlie Schlatter. He described the relationship as “brief” and “torrid”.

Daniel McDonald

Jen’s first love, Daniel McDonald, sadly died of a brain tumor in 2015, and she opened up about the loss during an interview with The New York Times. “He was my first love — five years we were together,” she said. “He would have been the one. But I was 25, and I was stupid. He must have sent me Justin to make up for it all.” Daniel’s widow, Mujah Maraini-Melehi, wasn’t happy about Jen’s comments and clapped back when she spoke to Inside Edition, ”I am sorry that Jennifer did not realize the treasure that was Daniel when she had the chance, long before he and I met and long before he died. It pains me to read the headlines that allude to her losing him tragically when in fact she was not present during his long and difficult illness.”

Adam Duritz

Jennifer dated Counting Crows frontman Adam Duritz for a brief period in the mid 90s, but ultimately called it quits. Neither have spoken much about their time together, however Adam revealed to Us Weekly that they “never slept together”, and he went on to date Jen’s pal Courteney Cox.

Tate Donovan

Jennifer dated her Friends co-star Tate Donovan, who had a six-episode arc as Joshua, the man her character developed a crush on after he came into her work. However, the pair actually began dating before he landed the gig, and they were going through a breakup at the time of filming. ““I was just happy to be on the team,” he revealed to Us Weekly in 2018 “The only bummer was Jennifer and I were breaking up at the time. And so 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. That was just tough.”

Brad Pitt

One of the most iconic couples of the early 2000s, who could forget Jen’s marriage, and subsequent divorce from Brad. The pair were rising stars in Hollywood at the turn of the century — they began dating in 1998 and said “I do” in 2000. After five years together, they called it quits, amid rumors he had an affair with his future wife Angelina Jolie. Despite the drama that surrounded their high-profile divorce, the pair appear to have remained friendly, even sparking reconciliation rumors at the 2020 SAG Awards.

Vince Vaughn

Following her first divorce, Jen was linked to actor Vince Vaughn in 2006. They did everything they could to avoid the paparazzi, given Jen was one of the biggest star’s in the world at the time, however Vince later admitted that the media attention was part of the reason they eventually split. Their joint statement at the time read, “After Jennifer’s trip to London several weeks ago, Jennifer and Vince mutually agreed to end their relationship but continue to be good friends today.”

John Mayer

Jen went on to date musician John Mayer. The Dead & Company singer and the Friends alum started dating in February 2008 after hitting it off at an Oscars party. The couple split that summer, but were back together by the February 2009 Academy Awards. They ended things for good shortly after that rare public appearance. While it’s unclear if the exes still speak, they’re clearly on good terms over a decade later given Jen dropped in on his Instagram Live earlier this year.

Bradley Cooper

Jen and Bradley Cooper reportedly had a brief romance in 2009 while he was filming “He’s Just Not That Into You”. Very little is known about the relationship, but the pair are believed to have remained friendly.

Justin Theroux

Jennifer first met Justin Theroux, her future second husband, on the set of Tropic Thunder in 2007. They made their relationship official in 2010 when they worked on the movie “Wanderlust” together, and revealed that they were engaged in 2012. They secretly tied the knot in a surprise ceremony in 2015, and the newlyweds jetted off to Bora Bora to enjoy their honeymoon. Nevertheless, in 2018 they announced they were splitting, and later divorced.