The Truth About Brad Pitt and Jennifer Aniston's Current Relationship

Nearly 15 years after Hollywood's golden couple announced the end of their love story, Brad Pitt and Jennifer Aniston are still there for each other when the rain (or the drinks!) begin to pour.

By Sarah Grossbart Dec 18, 2019 2:00 PMTags
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For those still 'shipping Brad Pitt and Jennifer Aniston, it was a dream scenario. 

Because there was the flaxen-haired boy himself, slipping into West Hollywood's Sunset Tower to fete his former wife's 50th birthday alongside the likes of George Clooney, Amal Clooney, Reese Witherspoon, Robert Downey Jr., Ellen DeGeneres, Barbra Streisand, Kate Hudson, Laura Dern, Demi Moore, Courteney Cox and Lisa Kudrow

It was a guest list so star-studded it could easily be mistaken for that of the Academy Awards, but for plenty of pop culture fans Pitt's was the only appearance that mattered. Coming nearly one year to the date after Aniston's shocking announcement that she and Justin Theroux had ended their two-and-a-half year union it was the sign: Clearly the universe had righted itself and Hollywood's golden couple was reuniting, their 2005 divorce and subsequent marriages just an unfortunate 14-year break. 

So let's all raise a tequila, lime juice and Cointreau margarita (no sugars, no agave) and celebrate, right? 

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While there may, indeed, be cause for revelry it's more that everyone involved in this once incredibly painful situation has found a way to close the door to the past and be cordial. Milestone birthdays can have that effect. 

An insider told E! News, "Someone extended the invitation to Brad to come to Jen's party and he accepted. He wanted to support Jen and it was a momentous occasion." 

Should she wish to return the favor and shoot him a text for his 56th birthday today, that would be fine, too. After all, they just saw each other at Aniston's annual Christmas fete. "They don't talk often but when they do its very warm and positive," said a source. "It's not as big of a deal to them as it is to everyone around them." Which is why neither half of the former golden couple is stressing about the fact that they may cross paths next month at the Golden Globes where each of their recent projects are up for awards.

"They've been in touch over the last few years and talk occasionally. If they run into each other they will congratulate each other and exchange pleasantries. They want the best for each other," explained the source. "There are no issues with being in the same place at the same time."

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Such was the case at Aniston's February bash, with The Morning Show star making the conscious decision to include everyone who had made some sort of impact on her life.

Pitt wasn't even her only ex present, what with John Mayer making the rounds mere steps away from his other ex Katy Perry and her new guy Orlando Bloom. Pitt's former fiancée Gwyneth Paltrow was also in attendance, dragging the birthday girl into the photo booth for a snap. Basically the event was a giant show-and-tell on what happens when everyone acts like grown-ups about the whole situation—when your friend asks you to come celebrate their existence, you deal with the fact that it may bring you face-to-face with a former lover. 

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"Every single person who loves Jen attended. That included Brad," a source told People. "The party was a celebration of Jen's life. Brad, for long, was a very important part of Jen's life. She debated back and forth with friends if she should invite him." In the end, the source continued, she was "very happy" that he showed. "Many of his close friends were at the party too." 

Which is good, because Aniston didn't really have time to play babysitter. While she greeted Pitt with a hug and took time for a quick chat, the source told People, "Jen was busy making sure all of her other guests had an amazing time." 

With the airy hotel terrace's pool and back bar decked out in white flowers and candles aplenty and a DJ hired for the occasion, the mood was set for fun and all of the bold-faced names took their turns greeting the birthday girl and offering up toasts. "It was a social evening with a lot of people who have been a part of her life," the insider told E! News. In other words, don't read too much into the fact that Pitt joined in. "They definitely aren't dating or on that path. They are friendly, but that's it." 

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Considering their history, though, that's fairly impressive. 

Staying friends with an ex is tough, harder still when you once thought of them as your person, the one you would maneuver through the rest of life alongside. Paired up by their agents in the spring of 1998, Pitt, having cemented his movie star status with Legends of the Fall, Se7en and Twelve Monkey, and the Friends standout knew "on our first date" that they were set to go down as one of the more successful matchmaking efforts in history, she would tell Diane Sawyer in January 2004. Though she was careful not to say it at the time, she revealed in that interview, "I thought it." 

Still, eager to preserve what was happening between them in that all-important getting-to-know-you phase, they remained intentionally cagey, even as Pitt was spotted at the Friends' 100th episode bash that fall or whisking the birthday girl off to Acapulco for a joint Valentine's Day-30th birthday celebration the following February. 

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Costar Kudrow shared her take on their successful pairing to Rolling Stone in March 1999. "There's not a lot to say about them because there's no problems," she shared. "They're both light-years ahead of themselves. You know how your grandparents have a certain perspective about life? They've got that now." 

But when asked to give her own thoughts, Aniston was less eager to oblige. "Oh, I hate this! I can't talk about it," she told the mag. "I'm sorry. I'm not withholding, just preserving something that's mine." Worried that gushing about their romance "trivializes something that's nobody's business," she would only offer up one platitude: "I'll just tell you that this is the happiest time of my life—that I'm happier than I've ever been. I'm not saying why, it's for a lot of reasons: work, love, family, just life—all of it."

That fall, the duo made their red carpet debut, their matching tans and perfectly styled tresses making them the prom king and queen of the Emmys. Who cared that Aniston was a year away from even being nominated? 

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And the following summer, they officially cemented their status as the power couple topping the Hollywood food chain. In some ways their million-dollar July 29, 2000 vows atop a Malibu cliff were as hush-hush as their initial courtship with guests, including Aniston's Friends cohorts and Pitt's Fight Club costar Edward Norton, having to wear pins to get past the security guards at the private estate. But they did slake fans' thirst with a few key details, sharing a single, black-and-white photo of Aniston in her beaded Lawrence Steele gown and Pitt in his Hedi Slimane tux and choice portions of their endearing vows. Pitt pledged to split the difference on the thermostat while Aniston promised to always make his favorite banana milkshake. 

"I had those typical jitters the day before my wedding," Aniston recalled to Rolling Stone in September 2001, "but the day of, I was just excited in a good way. The nice thing about weddings now is it's not just a chick thing. It's a team effort. The stereotype used to be men grumbling, like, 'Why are you making me do this?' There's nothing more moving than seeing a man cry at his own wedding."

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And with that milestone firmly put to bed, fans began anxiously anticipating the next. 

Aniston obliged the baby chatter—"I always thought two or three children, but Brad's definitely seven. He loves the idea of a huge family," she told the May 2001 issue of Vanity Fair—she also hinted that life with her best friend wasn't all matching highlights and a shared production company. (The couple joined up with late agent Brad Grey to form Plan B Entertainment—still a part of Pitt's portfolio as it churns out award winning fare such as 12 Years a Slave and Moonlight—in November 2001.) 

"This has been the hardest year of my life, as well as the best year of my life," she said. "Marriage brings up all the things I pushed to the back-burner—the fears, the mistrust, the doubts, the insecurities. It's like opening Pandora's box. Every question comes out—it's like: 'Here's the key, have at it!'"

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By 2003, they seem to have more or less figured it out, with Aniston admitting to W that February that of course they have arguments like any normal pair that has to figure out how to do life together. "Well, we have discussions," she said. "I am not a fan of fighting when it is screaming. I like accomplishing something. But I don't trust a couple that says they don't fight."

A fine, relatable answer, but the writer noted she seemed more stymied when asked if Pitt was the love of her life, a seeming softball of a question that the actress put an extraordinary amount of thought into. "Is he the love of my life? I think you're always sort of wondering, 'Are you the love of my life?'" she shared. "I mean, I don't know, I've never been someone who says, 'He's the love of my life.' He's certainly a big love in my life. I know that we have something special, especially in all this chaos. In this nutty, brilliant, wonderful, hard business that we have, it's nice to have somebody who's anchored and knows you, really knows all of you."

Brad Pitt's Dating History

In other words, yes, he pretty much was. Aniston was just not one to speak in absolutes. 

But her naked honesty kicked off a round of rumors that the golden pair was crumbling and forced Aniston to clarify her stance in her 2004 sit-down with Sawyer. Noting she hated reading the writer's take on her answer, particular their belief that she paused before speaking, she told Sawyer, "I can't imagine being with any other human being. I married him because he was the love of my life. And you know, he's the most fun I've ever had. So when these things are written in magazines and taken out of context, it's so frustrating because people then take it and run with it...Jesus, we were divorced and moving into different homes."

And while Aniston's characterization of how split speculation can run rampant in Hollywood was spot on, sometimes such stories turn out to be true. Because that spring Pitt would begin filming his latest action adventure flick about married assassins, unknowingly tasked with killing each other. Originally set to star Nicole Kidman, Mr. & Mrs. Smith would feature Pitt acting opposite that quirky young single mom, Angelina Jolie

20th Century Fox

"I didn't know much about exactly where Brad was in his personal life," Jolie would later tell the January 2007 issue of Vogue. "But it was clear he was with his best friend, someone he loves and respects. And so we were both living, I suppose, very full lives...I think we were the last two people who were looking for a relationship. I certainly wasn't. I was quite content to be a single mom."

But, as anyone with even a passing interest in pop culture now knows, that's not how this particular tale played out. "Because of the film, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened," she shared. "I think a few months in I realized, 'God, I can't wait to get to work.'...Anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair."

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It was an interview Aniston would later dub "uncool" in her own sit-down with Vogue and it was an apt way to label the whole situation. Because on Jan. 7, 2005, mere days after Aniston and Pitt went on a trip to Anguilla, a getaway that would prove to be their last as a couple, they were announcing their decision to "formally separate", their statement crafted carefully to illustrate that this was due to little more than two people going their separate ways. "For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media

Of course, it turned into a media circus nonetheless, an outcome that should have pretty much been expected given what happened next. 

Because that April, Pitt and Jolie were photographed on a Kenyan beach playing with Jolie's then 3-year-old son Maddox in a moment that could only be categorized as that of a happy family and by July they were willingly posing up with a set of lookalike kids for a photo-driven W feature titled "Domestic Bliss."

It was the latter in particular that would lead Aniston to famously declare her ex was missing "a sensitivity chip" when she granted her first post-divorce interview to Vanity Fair in September 2005. Though the beach tableau wasn't all that great, either. "I can't say it was one of the highlights of my year," she admitted. "Who would deal with that and say, 'Isn't that sweet! That looks like fun!'? But s--t happens. You joke and say, 'What doesn't kill you makes you stronger.'" 

Because while this chapter of her personal narrative wasn't the best—the whole world speculating on if and just how and why she had been jilted—she was not here to be anybody's victim. 

"Am I lonely? Yes. Am I upset? Yes. Am I confused? Yes. Do I have my days when I've thrown a little pity party for myself? Absolutely," she reasoned. "But I'm also doing really well. I've got an unbelievable support team, and I'm a tough cookie." 

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With the help of therapy, she insisted, she was feeling not only strong, but hopeful about what was lying ahead, just off in the distance. "You can't let the devastation of a divorce take over and win—let it make you this bitter, closed-off, angry, skeptical person," she explained. "Then you're just falling victim to it. You don't want to shut your heart down. You don't want to feel that when a marriage ends, your life is over. You can survive anything."

And while she admittedly wished she didn't have to chart her personal survival course in front of an audience of millions, she had already landed on the perfect coping strategy. Abandoning the Beverly Hills spread she once shared with Pitt, she had retreated to a serenely outfitted Malibu bungalow "in an effort to take care of myself and my heart." It was a spot where she could scream into the abyss of the Pacific Ocean ("Not too loudly," she cautioned. "You don't want people to think that you're crazy") and lean on her dearest friends.

And she could do so while sitting on the most cushy, the most enveloping of sofas. 

Stefanie Keenan/WireImage

Because while she kept quiet on the more unsavory details of her Pitt split and his decision to subsequently flaunt his romance, she did manage a few relatively harmless swipes. There was his new platinum coif to make fun of, after all ("Billy Idol called—he wants his look back,") and his penchant for filling their 12,000-square-foot Beverly Hills mansion with uncomfortable museum pieces. ("He definitely had his sense of style, and I definitely have my sense of style, and sometimes they clashed. I wasn't so much into modern.")

Asked if there's anything she had embraced post split, á la Nicole Kidman and her high heels, she responded, "I can have a comfortable couch.

That initial bombshell interview was certainly the one most mined for telling Pitt tidbits, but it was hardly the only one. Pretty much any time either half of the pair opened their mouth from 2005 until, now, basically, their words were destined to be parsed for signs they were either dissing—or embracing—their ex. 

In some instances, it was somewhat deserved, like the time Vogue splashed Aniston across their December 2008 cover with the pullout quote, "What Angelina Did Was Very Uncool." 

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Or the time Pitt tried to take a swing at himself and ended up squarely landing his jab on his ex. 

"I spent the '90s trying to hide out, trying to duck the full celebrity cacophony. I started to get sick of myself sitting on a couch, holding a joint, hiding out. It started feeling pathetic," Pitt told Parade in 2011. "It became very clear to me that I was intent on trying to find a movie about an interesting life, but I wasn't living an interesting life myself. I think that my marriage had something to do with it. Trying to pretend the marriage was something that it wasn't."

Dredging up old history and seemingly trying to drag his ex for his own issues landed the normally affable star in such hot water, he felt the need to explain himself in a statement to E! News. "It grieves me that this was interpreted this way [as a slam at Aniston]. Jen is an incredibly giving, loving, and hilarious woman who remains my friend. It is an important relationship I value greatly. The point I was trying to make is not that Jen was dull, but that I was becoming dull to myself—and that, I am responsible for."

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Either way, by 2015 Aniston was over the whole narrative. Yes, she had been married to a man she once declared her best friend and yes it all came unraveled under circumstances that could certainly be labeled as dubious, but hadn't they each moved on and done the work of successfully carrying about their own business for some time now? 

"The fact that it still follows you around—I mean, I'm divorced. It's gotta be painful," reporter Lee Cowan asked the actress on CBS Sunday Morning, while interjecting his own feelings about people bringing up his former marriage. 

"I don't find it painful, though," Aniston replied. "I think it's a narrative that follows you because it's an interesting headline. It's more of a media-driven topic." As was the idea that she and Jolie were still at odds, the actress secretly reveling in the fact that those Kitson Team Aniston shorts outsold Team Jolie many times over. "I think it's time people stop with that petty B.S. and start celebrating great work and stop with the petty kind of silliness," she told ET in remarking on Jolie's 2015 Critics' Choice Best Director nod for Unbroken. "It's just tiresome and old. It's like an old leather shoe."

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Wishing to put the entire saga to bed, she reiterated to The Hollywood Reporter that same year that she doesn't hold ill will or other similarly loaded feelings toward her ex or his bride. 

"We're not in daily communication. But we wish nothing but wonderful things for each other," she told the outlet. "Nobody did anything wrong. You know what I mean? It was just like, sometimes things [happen]. If the world only could just stop with the stupid, soap-opera bulls--t. There's no story. I mean, at this point it's starting to become—please, give more credit to these human beings."

So while her fans—and the hundreds of memes that they dreamt up—envisioned a smug Aniston taking in the news of Pitt's split from Jolie the following year, her role was more that of confidante, a familiar voice who's been there, dealt with that when it comes to the whole public breakup thing. A source told E! News at the time that the pair were in touch, categorizing their relationship as "friendly, but limited." 

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It's stayed much the same since, despite those hoping she would find herself in Pitt's arms in the wake of her Theroux split. "They do text from time to time and have exchanged a few words over the years, but there's nothing beyond that at this point," a source told E! News at the time. "She wishes Brad well, but that was a lifetime ago and they were both very different people back then."

More than three years on, they're firmly in the casual friends category in that they'll be there for each other when the rain—or the drinks—start to pour. "Brad and Jen talk or text once in awhile," the insider tells E! News. "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." 

So pretty much like the type of relationship one might maintain with a high school sweetheart that they've long moved past. "They don't talk or see each other all the time," notes the insider. "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."  

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Which is why Aniston, for all the sad sack narratives that tend to surround her, is able to label both of her past unions as ultimately fruitful ones. "I don't feel a void. I really don't," she explained in Elle's January issue. "My marriages, they've been very successful, in [my] personal opinion. And when they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness doesn't exist within that arrangement anymore."

But that doesn't mean you can't share a margarita, or a happy birthday wish, between friends. 

(Originally published February 11, 2019, at 12 p.m. PT)