Whether it’s a fling with a co-star or a full-on marriage, fans can’t seem to get enough of Aniston’s dating life. Now that the actress has recently sparked reconciliation rumors with her first ex-husband, Brad Pitt, many are thinking back to some of the 50-year-old star’s past romantic entanglements with fellow celebrities.
As fans wait for another flirty indication that the “Morning Show” actress may have another potential boyfriend in the wings, they can study up on who Aniston has dated publicly in the past:
Prior to her breakout role as Rachel Green on “Friends,” Aniston co-starred on a failed NBC series in 1990 based on the John Hughs movie “Ferris Bueller’s Day Off.” Although she played his sister, Jeannie Bueller, on the show, former GQ Editor-in-Chief Jim Nelson revealed in 2014 that she dated Charlie Schlatter, who played Ferris. Although the romance was brief, it marked one of the first of many showbusiness boyfriends for Aniston.
Aniston revealed in an interview with the New York Times in 2015 that she dated Daniel McDonald just before she landed her part in “Friends.”
“He would have been the one. But I was 25, and I was stupid,” she explained, not mentioning McDonald by name.
However, she also revealed that the boyfriend moved to New York and found success, but died years later of a brain tumor. The public put it together that the man was McDonald, a Tony nominee who died in 2007 long after they had already called it quits on the relationship.
Just as “Friends” was becoming a TV powerhouse and cultural phenomenon in 1995, Aniston was romantically linked to Adam Duritz, who was the frontman of one of America’s most popular bands at the time, Counting Crows.
According to InStyle, the duo were a Hollywood power couple for a little while but ultimately called it quits. No one quite knows exactly why they broke up as both stars have been relatively tight-lipped over the years about the entire relationship. However, Duritz revealed to Us Weekly that they never slept together.
After the breakup, though, he did go on to date Aniston’s “Friends” co-star Courteney Cox.
Shortly after her split with Duritz, Aniston started a romance with actor Tate Donovan. Many may remember Donovan as Joshua, the man Rachel develops a huge crush on after he came into her work to redo his wardrobe.
His six-episode arc, which did not end well for Rachel, was memorable to fans. However, the duo likely doesn’t remember the experience fondly as he revealed to Us Weekly in 2018 that they were breaking up during filming.
“I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,” he said. “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.”
Aniston's relationship with the "Once Upon a Time in Hollywood" star was not only one of her longest relationships to date, it was also her most serious.
Pitt and Aniston started dating in 1998 and eventually tied the knot in 2000. However, they had one of the most high-profile divorces in recent memory after five years together. Pitt was rumored to have had an affair with his "Mr. & Mrs. Smith" co-star, Angelina Jolie. They started dating soon after and Pitt married Jolie in 2014 but split in 2016. In 2019 their divorce was finalized. Aniston and Pitt remain friendly with each other despite the tabloid drama in 2005. During the 2020 Golden Globes and SAG Awards, they sparked reconciliation rumors after a couple of seemingly flirty encounters.
After her breakup with Pitt, Aniston went on the rebound with her co-star in the ironically titled 2006 romantic comedy, “The Breakup”--Vince Vaughn.
At the time, the duo tried to keep the relationship a secret for fear of the paparazzi in the wake of her very public breakup with the “Oceans 11” actor. Vaughn even admitted that the media attention played a part in their eventual breakup in a 2015 interview with Playboy.
Unfortunately for them, the duo was eventually forced to release a joint statement (via EOnline) that not only admitted to the romance but announced it was over.
"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," the statement read.
A year after her relationship with Vaughn came to an end, she was spotted out and about getting cozy with then-36-year-old British model Paul Sculfor. At the time, the duo were spotted in Los Angeles holding hands and being intimate, according to People.
However, the duo never made things official and the relationship fizzled out over time.
Aniston dated John Mayer off-and-on for about a year between 2008 and 2009. They were spotted out numerous times, but they eventually ended things for good.
Mayer previously hinted to Rolling Stone that the breakup was not exactly amicable.
“I've never really gotten over it," he told the outlet. "It was one of the worst times of my life."
He would go on to tell Playboy: “That pearl of possibility that lives in your heart when you meet somebody you want to know more about has such a different molecular density than everything else that you have to pursue it. And I wouldn’t undo it, man. Because if it had worked out, I would have reaped the benefits. I would be sitting here saying, 'What I have when I go home is the thing I’ve always wanted.'"
Aniston was said to have dated Bradley Cooper in 2009 for a very brief time. According to Us Weekly, they dated while filming “He’s Just Not That Into You” (a movie in which they shared no scenes). However, the “Silver Linings Playbook” actor eventually opted to engage in a serious relationship with Renee Zellweger rather than to take the next step with Aniston.
Aniston’s second serious relationship came after she met “Leftovers” star Justin Theroux in 2007 after being introduced on the set of “Tropic Thunder,” according to Us Weekly.
They started dating officially in 2010 after reconnecting to work on the movie “Wanderlust.” They made their relationship official in 2011 and revealed that they were engaged in 2012. Three years later, they tied the knot. However, in 2018 they revealed that they were separating, marking Aniston’s second divorce and last serious relationship to date.