Time to Dive Into Jennifer Aniston’s Complete Dating History

Jennifer Aniston has extremely excellent taste in most things, including but not limited to iconic haircuts that define entire eras, award-winning TV shows, and, well, partners. Obviously, we all know that JenAn was with Brad Pitt (some fan fiction-y corners of the internet think they’re getting back together), and was next married to Justin Theroux. But Jen’s also dated a few other A-listers in her day, from John Mayer (what) to Paul Rudd (what x 1,000). Without further ado, here’s a complete list of Jennifer Aniston’s ~lobsters~. (Get it? Ofc you do.)



Welcome to Jennifer’s first celebrity romance. Turns out Jen and Charlie met on the 1990 Ferris Bueller’s Day Off show (excuse me while I watch that immediately), and then in 2014, GQ’s Editor in Chief Jim Nelson casually announced that he witnessed their “brief, torrid” relationship when he was a writer’s assistant on said show. To quote:
“GQ can exclusively report that everyone on set thought she was hot, including Schlatter, with whom she had a brief, torrid romance—while playing, it must be said, his older sister. To we immaturions on the show, this seemed extra-hot. Like performative incest.”
Welp, this quote is all kinds of gross and sleazy, so moving on!


Paul and Jen were rumored to be an item sometime in their early careers, but honestly the internet wasn’t really a thing back then and no one was keeping up with Paul Rudd’s romantic life, so the details are murky at best. Jennifer did, however, admit that she and Paul were “together when we were, like, 12.”


JenAn and Daniel dated for over four years, which is a lifetime in celebrity relationships—which is why I find it truly wild that I have no memory of this ever happening! But apparently Jennifer was smitten because she opened up about her relationship with the late actor to The New York Times in 2015 (via Entertainment Tonight), saying “He was my first love—five years we were together. He would have been the one. But I was 25, and I was stupid. He must have sent me Justin [Theroux] to make up for it all.”


Jennifer and Counting Crows’ Adam Duritz dated for approximately two seconds before he went on to date her BFF and Friends co-star Courteney Cox. Of their brief fling, Adam told VICE TV’s Dark Side of the ’90s:

“A bunch of my friends lied to me and told me she had a crush on me. Those same friends lied to her and told her I had a crush on her.”
He went on to claim that he’d “never seen” Friends (sure, bud) and “honestly had no idea who she was.”

Gonna go ahead and say this is when Adam Duritz peaked even though he doesn’t seem to realize that.


Jennifer and Tate dated for a couple years, and then (awkward) he ended up getting a role on Friends (Joshua!) right as they were breaking up IRL. He told Us Weekly, “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.’”

BRAD PITT: 1998-2005

They got married in Malibu a few years later, but split up amid rumors that Brad was cheating with Angelina Jolie on the set of Mr. and Mrs. Smith. Photos eventually came out of Brad and Angie hanging out on the beach, pretty much confirming rumors of their new relationship, and Jennifer eventually spoke out about the pics in a 2006 Vanity Fair interview saying:

“The world was shocked, and I was shocked. I can’t say it was one of the highlights of my year. Who would deal with that and say, ‘Isn’t that sweet? That looks like fun!’? But sh*t happens. You joke and say, ‘What doesn’t kill you makes you stronger.’”
Anyway, it was super messy for a while there, but Brad and Jen appear to be on amazing terms these days and were even hanging out a bit before the pandemic, prompting speculation that they were reuniting.

VINCE VAUGHN: 2005-2006

Vince was Jennifer’s next serious relationship, but they didn’t last long, splitting in 2006. Jennifer opened up about the breakup to Vogue, saying, “I call Vince my defibrillator. 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.”

JOHN MAYER: 2008-2009

These two were kinda on and off from 2008 to 2009, and then John inexplicably held a press conference outside his gym to announce their eventual split. In 2010, he chatted about the experience to Rolling Stone, saying, “I’ve never really gotten over it. It was one of the worst times of my life.”

More recently, John has been spotted lurking on Jen’s Insta. By which I mean…he liked this photo in 2020 and the internet lost it:


Justin and Jen started dating after filming Wanderlust together, and got married in 2015. But they split up in 2018—though everything was super amicable and they’re still close friends.

Earlier this year, Justin told Esquire, “I would say we’ve remained friends. We don’t talk every day, but we call each other. We FaceTime. We text. Like it or not, we didn’t have that dramatic split, and we love each other. I’m sincere when I say that I cherish our friendship. We can not be together and still bring each other joy and friendship. Also, she makes me laugh very, very hard. She’s a hilarious person. It would be a loss if we weren’t in contact, for me personally. And I’d like to think the same for her.”


Jen and David dealt with fast and furious dating rumors recently thanks to a source telling Closer that after the Friends reunion, “It became clear that reminiscing over the past had stirred up feelings for both of them and that chemistry they’d always had to bury was still there. They began texting immediately after filming and, just last month, David flew from his home in New York to see Jen in LA.”

If that sounds like fan fiction, it’s ’cause it is! Celebrity gossip account @DeuxMoi shut down the story, while David’s rep told The Huffington Post UK that the rumors about him and Jen are simply not true.

It’s unclear who Jennifer is dating now, if anyone, but naturally she wants to keep it private, so on that note, BYE!

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