How Jennifer Aniston Has Mastered the Art of Being Friends With Her Exes

To be sure, Jennifer Aniston never rushed into pretending that all was hunky-dory after a breakup, but she's since proved that time can work wonders when it comes to restoring a lost connection.

By Natalie Finn Aug 17, 2021 5:30 PMTags
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Jennifer Aniston is into a lot. 

Her beloved dogs, yoga, philanthropy, taking good care of herself, the beach, sunny vacations, lavishing her tight circle of friends with generosity and affection. And acting, of course, the star of screens big and small having replenished her love of the game with her juicy, SAG Award-winning role on The Morning Show.

She knows it's a good life, one that shouldn't be taken for granted—or wasted on negativity.

So, among the things Aniston is just not that into? Bad blood, for one.

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"I'm a forgiving person. I think it's extremely important to forgive," she explained to Harper's Bazaar in 2014. "Otherwise it just builds up like toxic waste. There's nothing worse than holding a grudge. Listen, people can do unforgivable things, but you have to let it go and say, 'Look, we're all human beings. We make mistakes.' To hold any kind of resentment is like taking rat poison and waiting for the rat to die."

The actress added, "I'd rather just focus on people and things that are here, happening, and what's yet to come. My friends, my family, wonderful people I work with. We know what the real is."


The 52-year-old wasn't always so centered, having admitted that she's spent precious moments fuming, ruing and otherwise paying too much attention to a public narrative that often had her unwittingly on the receiving end of some romantic slight or another.

Which, here and there, she was. But isn't everybody?

"How many times can I be out there in the world, enjoying my life, and yet the narrative is 'Poor, Sorry, Sad in Love Jen' … whatever the stupid headline is," Aniston noted. And when told there had recently been a more upbeat headline about her prospects for happiness, she deadpanned, "Oh, thank God. Am I finally all right?"

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Of course, all of that stemmed from the dramatic ending of her not-quite-five-year marriage to Brad Pitt. While she'd dated others since and was engaged to Justin Theroux when she gave that interview, Aniston's world had been shockingly knocked off its axis back in 2005—and to many, that's how it remained years later, despite her having long been back on track. 

In fact, it may not have been until Pitt showed up at her 50th birthday party in 2019 that a lot of folks realized, Hmm, maybe Jen Aniston is having an OK time of it after all!

Not because she and Pitt were rekindling the flame following her divorce from Theroux the previous year, as a strikingly large number of people hoped they would the second they were both single again. (Such things do happen, after all.) Rather, because it soon donned on people that, holy smoke, Pitt and Aniston were...

"You know, Brad and I are buddies. Like, we're friends and we speak," she explained on The Howard Stern Show this June when asked if it was awkward to see Pitt (on Zoom) last year during a table read of Fast Times at Ridgemont High. Subsequently, she added, "There's no oddness at all, except for everyone that probably watched it and was wanting there to be."

Emma McIntyre/Getty Images for Turner

Not to mention, they'd seen plenty of each other in person, including at the aforementioned birthday party, the 2020 Golden Globes and then at the SAG Awards. Which is where the Outstanding Performance by an Actor in a Supporting Role in a Film winner caught his ex's Outstanding Performance by a Female Actor in a Drama Series speech on a screen backstage—and then they exchanged warm pleasantries right to each other's faces (and with their arms around each other), prompting an outpouring of a feeling to which the word "excitement" does no justice.

Aniston also couldn't avoid talking about the one with Brad Pitt while strolling down memory lane with her Friends co-stars in honor of their hotly anticipated, pandemic-delayed reunion special, currently being re-re-re-streamed on HBO Max. "Mr. Pitt was wonderful," she said on Access Hollywood of her then-husband's 2001 turn as former classmate Will, co-founder of their high school's "I Hate Rachel Club."

Not that Aniston necessarily ever envisioned being Pitt's buddy when they first split up and he quickly made it known he was all in on building a family with Angelina Jolie. She took no pains to hide that it was a really traumatic time for her and, a few months after the advent of "Brangelina," she still had her bad days. At the same time, she never burned the bridge, telling Vanity Fair in her spectacularly candid first post-breakup interview, "I'm not interested in taking public potshots. It's not my concern anymore. What happened to him after the separation—it's his life now."

Nor was it her concern, when they later resumed communication, if Pitt ever got around to having that "sensitivity chip" installed or not. In our humble opinion, he did, but regardless, that's the best part about being friends—it no longer matters whether the other person is romantic-relationship material or not!

"We have exchanged a few very kind hellos and wishing you wells and sending you love and congratulations on your babies," Aniston told Vogue of the state of her relationship with Pitt in 2008. "I have nothing but absolute admiration for him, and…I'm proud of him! I think he's really done some amazing things."

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Moreover, "it never was that bad," she added, referring to the endless woe-is-Jen headlines that followed their breakup. She explained, "I mean, look, it's not like divorce is something that you go, 'Oooh, I can't wait to get divorced!' It doesn't feel like a tickle. But I've got to tell you, it's so vague at this point, it's so faraway in my mind, I can't even remember the darkness."

In fact, Aniston recalled, "pretty soon after we separated, we got on the phone and we had a long, long conversation with each other and said a lot of things, and ever since we've been unbelievably warm and respectful of each other. Whoever said everything has to be forever, that's setting your hopes too high. It's too much pressure. And I think if you put that pressure on yourself—because I did! Fairy tale! It has to be the right one!—that's unattainable."

And that equitable place of mutual admiration was where they remained.


"Brad and Jen talk or text once in a while," a source shared with E! News after he joined the festivities for her 50th in 2019. "If something comes up like a birthday or a big occasion they will reach out and congratulate the other. They show support or exchange funny stories if something comes up. They don't talk or see each other all the time. They aren't a big part of each other's lives currently, but they wish each other well and have fond memories about the good times they had together."

Scars do fade after time, especially if you refrain from picking at them.

On the Friends reunion special this summer, Aniston and David Schwimmer cited their respective pre-existing relationships as the main reason why they didn't indulge their very real Ross-and-Rachel chemistry that was bubbling up behind the scenes in the late 1990s. On her end, she had been dating Tate Donovan for a couple of years—though they broke up before he was cast in the recurring guest role of Rachel's love interest Joshua. Which, per his recollection, was agonizing.

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"I was like, maybe it would be good to work through this breakup," he recalled on HuffPost Live in 2013, laughing at the memory. "What an idiot [I was]...It was bad." She thought it was a joke when he told her they wanted him for the part, but they both thought it might be cathartic. "It was horrible," Donovan said. "It was so tough, man. Oh, gosh. I remember just getting back to my dressing room and just weeping. It was tough. Could you imagine?"

And still, the bridge didn't burn.

Running into his exes in Hollywood was "awkward but also wonderful," Donovan noted. "You've both moved on and found other loves, and, you know, you have this great smile and I don't know—I generally enjoy it."

Apprised of the fact that he had told a reporter in 2013 that he was "very happy" for Aniston upon hearing of her engagement to Theroux, Donovan laughed and said, "I am happy for her."

Alice S. Hall/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images

Fast-forward to now and it wasn't a huge surprise when Aniston marked Theroux's 50th birthday on Instagram Aug. 10 by posting a couple of photos as tribute, including a shirtless shot of him on which she wrote, "Truly one of a kind. LOVE YOU!" (She only joined Instagram in 2019, but Theroux, on since 2015, has wished her happy birthday every year.)

They had indeed called themselves "two best friends who have decided to part ways as a couple but look forward to continuing our cherished friendship" in their Feb. 15, 2018, separation statement, but that isn't always a check a couple of actors can cash. Then again, the fact that they spent New Year's Eve on vacation together with pals after deciding to separate and then agreed to announce their split the day after Valentine's Day were indicators that they truly were comfortable being friends—and still shared the same wry sense of humor.

Theroux confirmed as much to the New York Times, calling their breakup "kind of the most gentle separation, in that there was no animosity. In a weird way, just sort of navigating the inevitable perception of it is the exhausting part."

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He was not invited to Aniston's 50th in February 2019 (a girl does need her space), but he still noted the occasion online—"Happy Birthday to this fierce Woman. Fiercely loving. Fiercely kind...and fiercely funny"—and they reunited a few months after that to say goodbye to Dolly, the German shepherd Aniston adopted in 2006 but who became theirs over the years.

The humans "weren't right for each other, but they did share a lot of great years," a source told E! News. "Their dogs were a big part of their life together. Even though Dolly stayed with Jen when they split up, Justin loved her hard. They're grieving her loss together, and it's a tough one."

Instagram/Justin Theroux

Terms were good enough that they didn't have to divvy up their mutual friends in the divorce, either, both exes joining longtime pals Jason Bateman, Jimmy Kimmel, Courteney Cox and more for Thanksgiving in 2019.

And they haven't stopped checking in, Theroux telling Esquire earlier this year, "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."

Speaking for both them and the whole art of remaining friends, "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." 

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Meanwhile, whether there's a lot to forgive (Pitt) or a little (more on that in a minute), Aniston has stayed consistent when it comes to taking the high road.

After their 2008 fling first ended (it would continue off and on till 2009), John Mayer told some paparazzi outside his gym that they were looking at "a man who ended a relationship."

Aniston shrugged off his apparent need to mention that he was the one who ended it ("especially because it's me," she said) and graciously told Vogue in 2008 that it didn't "take away from the fact that he is a wonderful guy. We care about each other. It's funny when you hit a place in a relationship and you both realize, we maybe need to do something else, but you still really, really love each other. It's painful."

"There was no malicious intent," she added. "I deeply, deeply care about him; we talk, we adore one another. And that's where it is."

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Mayer couldn't help but pour salt on his own wounds when he told Playboy in 2010 that there was a part of him that wished it would have worked out between him and Aniston, but "I can't change the fact that I need to be 32."

There are countless reasons why he'd come to regret that interview down the road, but Aniston (who's eight years older than him in regular years and infinitely older in maturity years) didn't take his infamous instance of oversharing too personally.

A source told Us Weekly in April 2020—after the Internet was alerted to a ripple in the Force by Aniston responding to some signature Mayer-brand self-deprecation with crying-laughing emojis on Instagram—that the singer and the actress "have a nice friendship. John has a deep admiration and respect for Jen."


Aniston also has nothing but platonic love for Vince Vaughn, her co-star in 2006's The Break-Up but not so much in a breakup, the actors' relationship eventually fizzling naturally with no hard feelings.

They tried their best to play it down early on ("I barely know the guy," she told Vanity Fair in 2005) but their constant paparazzi escort soon revealed that they were having a blast together.

"I call Vince my defibrillator," Aniston told Vogue in 2008 of her first post-Pitt romance. "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."

And that, my friends, is what they call perspective.