Before landing her breakout role as Rachel Green on Friends, Aniston starred in the short-lived TV adaptation of the movie Ferris Bueller's Day Off. During that time, she reportedly romanced Charlie Schlatter, her co-star, though the relationship wasn’t revealed until years later. According to GQ’s Jim Nelson (who served as a comedy writer’s assistant on the project), he witnessed Aniston and Schlatter’s “brief, torrid romance" on set, but neither Aniston nor Schlatter has ever confirmed the reported affair.

During a January 2015 interview with the New York Times, Aniston opened up about her relationship with actor Daniel McDonald, who she referred to as her “first love” and who died from brain cancer in 2007. According to Aniston, she and McDonald dated for five years before going their separate ways. “He would have been the one. But I was 25, and I was stupid,” she said of McDonald. “He must have sent me Justin [Theroux] to make up for it all.”

Little is known about Aniston’s relationship with Counting Crows frontman Adam Duritz, but the two briefly dated in sometime in 1995. Aniston has never spoken about the relationship, and Duritz only confirmed they “never even slept together,” per Us Weekly. Duritz went on to date Aniston’s real-life BFF Courteney Cox for a bit, and of dating the two friends, he simply told Men’s Health in September 2014, “They were nice girls and I went out with them and that was that."

Following her brief romance with Duritz, Aniston went on to date actor Tate Donovan, who she met in late 1995 through mutual friends. “He’s so real, so honest, so funny, so kind and considerate,” she gushed to People during an August 1997 interview. “He’s all these things meshed into one perfect guy.” Donovan even popped the question in 1998, but they called off the engagement soon after. And it wasn’t long before Donovan landed a six-episode arc on Friends, forcing him to work alongside his ex-fiancée.

“I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,” Donovan told Us Weekly in September 2018. “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.”

Before starring alongside him in the rom-com The Object of My Affection, Aniston briefly dated Paul Rudd, and he later confirmed the romance during an August 2011 interview with Elle, joking they were together “when we were, like, 12.” They also starred alongside each other in the Newton Boys and were Friends cast mates for two years, and when asked by GQ in February 2012 whether it’s weird for them to kiss onscreen as longtime friends, Aniston jokingly replied, “Nah. I’ve kissed him for years.”

Though Aniston first met Brad Pitt back in 1994 through their respective managers, they didn’t become an item until 1998, which is when they went on their first date. In a September 2001 interview with Rolling Stone, Jen explained that their managers set them up on that first outing. "He was this sweet guy from Missouri, you know?" she said of Brad. "A normal guy." The following year, they made their debut as a couple at the 1999 Emmy Awards, and by November 1999, they were engaged.

In July 2000, Pitt and Aniston tied the knot in Malibu. Everything seemed to be going swimmingly (Pitt even appeared alongside Aniston on Friends!) until January 2005, when the two announced their decision to separate. It took nearly a year for the exes to finalize their divorce, but in a September 2005 interview with Vanity Fair, Aniston said the process was amicable. "We exited this relationship as beautifully as we entered it," she said. During the interview, she also acknowledged the rumors about Pitt moving on with his Mr. and Mrs. Smith co-star Angelina Jolie, saying, “The world was shocked, and I was shocked. I can't say it was one of the highlights of my year.”

During a January 2015 interview with The Hollywood Reporter, Aniston made it clear she had no ill will towards her ex. “We're not in daily communication. But we wish nothing but wonderful things for each other,” she said at the time. “Nobody did anything wrong.” And in January 2020, the two even sparked reconciliation rumors when they shared a cute moment at the SAG Awards, but nothing ever came of the exchange publicly.

After separating from Pitt, Aniston began romancing her co-star from The Break-Up, Vince Vaughn in the summer of 2005. The two quietly dated for about a year and a half (all while denying their relationship), but by December 2006, the couple called it quits. “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,” their reps told People in a statement. Luckily, it seems things ended on good terms.

Two years after the breakup news went public, Aniston reflected on the relationship during a December 2008 interview with Vogue. “I call Vince my defibrillator," she said. "He literally brought me back to life. My first gasp of air was a big laugh! It was great. I love him. He's a bull in a china shop. He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course."

After a brief fling with British model Paul Sculfor, Aniston crossed paths with John Mayer at a 2008 Oscars party. "Barely knew his music," Aniston joked to Vogue during her December 2008 interview. "And then we ran into each other a week later, and that was that." She and the musician dated on-and-off-again for just over a year before they split for good in March 2009. "They had a great time at the Oscars, but he seemed to go cold right after that," a source claimed to the Sun. "To say her feelings are hurt is an understatement."

Mayer later expressed regret about their breakup, telling Rolling Stone in January 2010 he “never really gotten over it” and their breakup “was one of the worst times of [his] life." Fans thought the two might be hanging out again when it appeared their dogs had matching collars, but Aniston quickly cleared up the dating rumors during an August 2021 interview with InStyle. When asked about the similar dog collars, she said, “It's funny you should say that, because the collars are so cool," she said. "My trainer's friend makes them — the brand is called RN Design.” So much for that.

Aniston’s most recent romance was with actor Justin Theroux. The two met on the set of Tropic Thunder in 2007, but they didn’t start dating until they reconnected on the set of Wanderlust four years later. After just about a year of dating, Theroux popped the question in August 2012, and three years later, they said “I do” in a secret ceremony at their L.A. home. Fans were then shocked when the pair announced their decision to separate in February 2018.

In a joint statement, the two said, “This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship.” And luckily, it seems like that has remained true. “Like it or not, we didn’t have that dramatic split, and we love each other,” Theroux told Esquire in April 2021. “I’m sincere when I say that I cherish our friendship. We can not be together and still bring each other joy and friendship.”