A Timeline Of The Ups And Downs Of Brad Pitt And Jennifer Aniston's Relationship

Jennifer Aniston and Brad Pitt broke up more than 15 years ago, but even today, their love story is the thing of tabloid legends. It's a modern Shakespearean tragedy — with all the ups, downs, betrayals, and redemption arcs of the most classic Hollywood tales. It's the kind of epic romance that launched a thousand headlines, and it's been looking for a resolve for well over a decade. 

At the time, both actors were at the height of their massive careers. Aniston's run on Friends had spawned an iconic haircut as well as a record-number of viewers (8.6 million for the finale, according to BBC News, and that was just in the UK). Pitt was in the midst of landing some of his most revered roles in films like Se7en, Fight Club, and The Mexican. But the higher Hollywood romances rise, the harder they fall. 

Aniston and Pitt's split couldn't have been more dramatic if the tabloids invented it themselves (though, we're certain some tabloids invented some salacious plot points). Aniston was positioned as the heartbroken and scorned girl next door, and Angelina Jolie as the dangerous other woman who once wore a vial of her lover's blood (it was all, quite frankly, sexist and needs to stop). Since then, the former couple never actually left headlines. Here's a look inside the pair's iconic love story. It may not have the ending we wanted, but it's a happy ending nonetheless.

Jennifer Aniston and Brad Pitt's enduring love story began in 1994 in the most Hollywood of ways. The pair were introduced through their managers, who were friends. In an interview with Rolling Stone, Aniston revealed she initially thought Pitt, who was just one year away from becoming People's "sexiest man alive," was "a normal guy." She said, "He was just this sweet guy from Missouri, you know?" Thus, the greatest love story of the TMZ generation — with all of its coordinated his-and-hers chunky highlights — was born. Still, it took some time for things to turn romantic.

When the two first locked eyes on that fateful day in 1994, the actors were both in other relationships. Aniston was dating actor Tate Donovan, who starred alongside her in a string of Friends episodes. Pitt was dating Goop queen Gwyneth Paltrow, whose love affair was immortalized in an onslaught of tabloid headlines and that epic scene in Se7en where Paltrow's decapitated head was stuffed into a box.

Pitt, who called Paltrow "the love of my life" at the 1996 Golden Globes, ended up popping the question to Gwyn that same year. Aniston, on the other hand, split from Donovan in 1994 during his six-episode Friends run. He told Us Weekly that he was "sort of dying inside" while filming with the actress during their breakup. Awkward.

Four years after initially meeting, Jennifer Aniston and Brad Pitt finally went on their first date. According to Rolling Stone, the pair had already split from their previous partners — with Pitt breaking his engagement — and their managers penciled it in. It was basically love at second sight (or a really long rebound, depending on your level of cynicism).

In a Primetime interview, where Aniston was asked if she knew that Pitt was the one, she revealed to Diane Sawyer, "Yeah. We both did. On our first date. It was weird ... I thought it ... That was a really easy evening. That was really fun."

Even though the couple were almost constantly chased by paparazzi, it turned out they were just like everyone else beneath the surface. In her Rolling Stone interview, Aniston revealed that they bonded over music. They listened "to a lot of Radiohead," which the actress claimed "just sounded so good at that point in our relationship." We're guessing she's not talking about "Creep."

There's a few reasons 1999 will go down in the history books — the onset of Y2K, Lil' Kim's VMAs pasty, Bill Clinton's impeachment trial, the Who Wants to Be a Millionaire? premiere. But none of those things held the same pop cultural magnitude as Brad Pitt and Jennifer Aniston's public debut as a couple. After months of romance rumors, Pitt donned those sunglasses and that facial hair to walk down the red carpet at the Emmy Awards with the Friends actress for the first time. 

Aniston wouldn't win for her role as Rachel Green until 2002, but we'd argue that this moment was far more monumental. Things escalated quickly from there. Later that year, Aniston and Pitt jumped on stage at a Sting concert, presumably not to sing a haphazard rendition of "Smelly Cat." In one fell swoop, they inadvertently announced their engagement as onlookers spotted the star's massive engagement ring, according to Us Weekly. The Mirror reports that the ring was worth an estimated $500,000.

When the millennium bug didn't send civilization into total anarchy, Jennifer Aniston and Brad Pitt tied the knot. Brides reports that the couple got hitched in a "big, flashy, incredibly traditional" ceremony that cost about $1 million and included "200 of their closest friends."

According to People, the outdoor nuptials took place in Malibu, and had a "Zen garden look" at the request of the groom. It was lit by imported "candles made from brown sugar" for an extra-romantic touch, as requested by the bride. Because it was the year 2000, both actors reportedly "got matching 'brother-and-sister' blond highlights." They also had a 40-member gospel choir and allegedly required staff to sign NDAs, which mandated a fine of up to $100,000 if they spilled the matrimonial tea. In a move that could have been seen as a harbinger of the pair's tumultuous future, Pitt's brother and best man, Doug, supposedly dropped the ring.

Either way, the ceremony was sweet. Aniston vowed to always make Pitt's "favorite banana milkshake." Pitt vowed to "split the difference on the thermostat." All of Aniston's pals seemingly approved. "My friends were all supportive," Aniston told Rolling Stone in 2001. "Especially when they found out what a loving human being Brad is. At first they're like, 'I hope he's not an a**hole, some conceited f**k or whatever.' But you get past that in five minutes. Which is a real tribute to who he is. He just disarms you immediately."

After spending two blissful years as newlyweds, the first chips began showing in the couple's pristine porcelain veneers. Though Brad Pitt was so willing to admit that Gwyneth Paltrow was the love of his life, Jennifer Aniston wasn't sure she could say the same thing about their new relationship. When asked in early 2003 by W magazine about how it "feels to have found the love of her life," Aniston quickly recoiled.

"Is he the love of my life? I think you're always sort of wondering, 'Are you the love of my life?' 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," Anison admitted. "And I know that we have something special, especially in all this chaos." 

Nonetheless, these doubts seemed short-lived. The following year, Aniston revealed to The Guardian that she felt like it was time for pair to start having kids. She was "looking forward to slowing down" and planned on being a working mom.

By 2004, Jennifer Aniston wanted to start settling down. She was wrapping up Friends, and Brad Pitt was wrapping up Mr. & Mrs. Smith, in which he starred alongside Angelina Jolie. In an interview with The Guardian, Aniston admitted that she planned to spend some quality time with her husband while he began work on Ocean's Twelve. "I, thankfully, will be able to go and travel with him while he's doing that," she said. Little did she know that 2004 wouldn't just see the finale of her beloved sitcom. It would also see the finale of her marriage.

According to Entertainment Weekly, rumors of an affair between Pitt and Jolie began surfacing that May. They were reportedly fierce enough to warrant a cover story in Star and a "Hot Topic" in Us Weekly. In a bombshell interview with Vogue (via People), Jolie later revealed that neither her nor Pitt "were looking for a relationship," but they started to realize their bond was much deeper as they neared the end of filming their movie. 

"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," Jolie said. "I think a few months in I realized, 'God, I can't wait to get to work.' ... We just became kind of a pair."

In January 2005, Brad Pitt and Jennifer Aniston shocked fans by announcing their separation. In a statement to People, the couple slammed the tabloids' fixation on what would later be widely known as Brangelina. "... After seven years together we have decided to formally separate," the joint statement read. "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. This decision is the result of much thoughtful consideration." Two months later, Aniston officially filed for divorce, citing "irreconcilable differences."

Since the split, Pitt has remained adamant that he never cheated on Aniston with Angelina Jolie, though the rumors outlived both of his marriages. According to Marie Claire, the actor clarified the timeline. "We were still filming after Jen and I split up," he said. "Even then it doesn't mean that there was some kind of dastardly affair. There wasn't. I'm very proud of the way that it was handled. It was respectful."

Meanwhile, Aniston reportedly dubbed the whole thing "uncool." Falling in love with a co-star when you're already married is, indeed, a party foul.

As one of the most salacious Hollywood splits outside of Debbie Reynolds and Eddie Fisher, the media was clamoring at a chance to get any information about Jennifer Aniston's divorce. Who was at fault? Did Brad Pitt really cheat? Was it actually mutual? The Friends actress finally opened up in a bombshell Vanity Fair interview in September 2005. There, she admitted that she was publicly humiliated by Pitt and Angelina Jolie's high-profile relationship, which was featured in a 60-page W magazine photo spread that reportedly "horrified" Aniston's friends. To add insult to injury, Pitt had conceptualized the entire feature, entitled "Domestic Bliss."

"I would be a robot if I said I didn't feel moments of anger, of hurt, of embarrassment," Aniston told Vanity Fair, adding her now-famous quip that Pitt has "a sensitivity chip that's missing." In that same interview, Aniston also revealed that she was relying on therapy to get her through. "Am I lonely? Yes. Am I upset? Yes. Am I confused? Yes," she said. "Do I have my days when I've thrown a little pity party for myself? Absolutely. But I'm also doing really well. I've got an unbelievable support team, and I'm a tough cookie."

Brad Pitt and Jennifer Aniston appeared to steer clear of each other for about a decade, but then something happened: Pitt and Angelina Jolie hit a rough patch in 2017, which ultimately resulted in a divorce. According to Us Weekly, that's when the Fight Club actor decided to reconnect with his ex. At the time, the pair had reportedly "been texting," and Aniston's then-husband, Justin Theroux (who she married in 2015), was allegedly "ok with them being friends." That marriage didn't last either, but her bond to Pitt did.

Us Weekly reports that Pitt and Aniston hashed it out in May 2016 after the actress' mother passed away. "Brad contacted Jen after her mom died, and she was touched that he knew what a difficult time it was," a source told the tabloid. A separate report from ET revealed that Pitt had, at one point, attempted to make amends. "He has apologized to her for many things he felt were his issues in their relationship," an insider claimed. "He truly takes ownership for his mistakes and that has changed their relationship with each other today. They both have moved on."

During this time, the pair had reportedly become "much closer friends" than they were when they were together, and they allegedly "love[d] and adore[d] each other."

At the onset of her golden birthday year, Jennifer Aniston was in a really good place. She had split from her second husband, but had no regrets about either of her marriages, even the one that spawned leagues of nasty tabloid rumors that she never fully managed to escape from. 

In a 2018 interview with Vanity Fair, Aniston revealed, "I don't feel a void. I really don't. 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 didn't exist within that arrangement anymore."

It was the perfect time for ex Brad Pitt to swoop in, and swoop he did. The former couple made headlines when Pitt was spotted at Aniston's 50th birthday party at the Sunset Tower Hotel in Los Angeles in February 2019. According to two separate reports from Us Weekly, the pair had been "getting close" since Pitt's split and were "flirtatious at times" with an "infectious energy." Still, they insisted their interactions were strictly platonic, despite the fact that Pitt reportedly attended Aniston's Christmas party that same year. Hello, it was cuffing season!

If Jennifer Aniston's birthday party was the spark that ignited rumors of a rekindled romance, an event the following year burned the whole thing down. According to Vanity Fair, both parties attended the Golden Globes in January 2020, which marked Pitt's first win since 1996. On the red carpet, Pitt told ET that Aniston was his "good friend," and Aniston looked ultra-emotional during his acceptance speech. To boot, The U.S. Sun noted that the actress was sporting a ring similar to her old engagement ring.

Flash forward to the SAG Awards weeks later, and the reverse happened. According to The U.S. Sun, Aniston won her first SAG Award since 1996. Pitt watched from backstage and appeared to be beaming. He even reportedly said, "Oh wow," when she took the stage, and the pair had their first public photo op in more than a decade. They were nothing but smiles.

While this heightened the already ferocious romance rumors, a source that spoke to People shut it all down. "They are friends and happy for each other. They want nothing but happiness for each other," the insider said. "She is happy to have Brad back in her life as a friend, but that's it."

Though the Australian tabloid New Idea claimed that Brad Pitt and Jennifer Aniston were officially getting back together in April 2020, it doesn't seem like that was ever actually the case. (We can dream, right?) Apparently, the rumors are all a big joke to the former couple, who have made a game out of toying with our fragile hearts at a time when we need some — any – good news. A source told Us Weekly that they think it's "hysterical that fans are so obsessed with them getting back together."

At the time of this writing, Aniston appears to be single, but Pitt is reportedly in a torrid romance with a much younger, married woman. According to the Daily Mail, the actor's new gal, 27-year-old Nicole Poturalski, is married to 68-year-old German restaurateur Roland Mary, with whom she shares a 7-year-old child. Pitt reportedly became chummy with Mary while filming Inglourious Basterds in Germany, and "fell in love" with Poturalski after meeting the model in Mary's restaurant in 2019 during the Once Upon a Time... In Hollywood promotional tour. 

This isn't as salacious as it sounds, though. Per the tabloid's report, Poturalski is in an open marriage. We can probably all agree that Pitt's not so shabby for a side piece.