Justin! Brad! A Timeline of Jennifer Aniston’s Dating History

Jennifer Aniston has been married and divorced twice, but she still believes her Prince Charming is out there. “She hasn’t given up on love,” a source told Us Weekly exclusively in November. “It’s not in her nature to give up or be negative.”

The insider added that the We’re the Millers actress is “not trying to force” a relationship and would be “open to dating” if something came along organically. To see everyone Aniston has romanced in the past, keep scrolling!

Charlie Schlatter

Before she started playing Rachel Green on Friends, Aniston starred on the short-lived 1990 TV adaptation of the John Hughes film Ferris Bueller’s Day Off. It wasn’t until 14 years later, however, that the actress’ romance with her costar was revealed. Jim Nelson, the former head of GQ magazine, revealed in April 2014 that he witnessed the actors’ “brief, torrid” relationship, as he was a comedy writer’s assistant on the project at the time.

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Daniel McDonald

The Dumplin’ actress called McDonald her “first love” in a January 2015 interview with The New York Times. Aniston and McDonald, who later died from brain cancer, dated for five years before they called it quits. “He would have been the one. But I was 25, and I was stupid,” Aniston explained. McDonald’s widow, Mujah Maraini-Melehi, was not happy about the Switch star’s comments and later told 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.”

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Jon Stewart

The comedian and the actress went out on one date almost 20 years ago. “I asked you out and it was lovely,” Stewart reminded Aniston on The Daily Show in August 2010. “I remember you brought so many of your friends. And I remember thinking, ‘She’s so excited to be on a date wth me, she wants me to get to know her posse.’” The Office Christmas Party star had a different memory of the incident and rebutted, “If I remember correctly, wasn’t it sort of like, ‘Hey, a group of us are going out, do you want to join?’”

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Adam Duritz

Talk about an unlikely couple! Aniston and the Counting Crows frontman briefly dated in 1995, but the musician later admitted that they “never even slept together.” After their split, Duritz moved on with Aniston’s Friends costar and real-life best friend, Courteney Cox.

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Tate Donovan

Donovan was thrilled to land a six-episode arc on Friends in 1998, but the gig was bittersweet, as he and Aniston were splitting at the same time. “I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,” the Argo actor 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.”

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