Celebrity relationships and friendships are a rare breed. These famous faces have their lives played out in front of the masses, whether it’s the good, the bad, or the straight-up shady. In Elite Daily’s new series, It’s Complicated, we’re highlighting the biggest celebrity “feuds” that took over Hollywood and dominated our Sunday brunches for weeks on end. We’ll take a deep dive into the lives and social media feeds of our favorite stars and dissect what happened in front of the camera, what went down behind the scenes, and everything you might have missed in between.
Hearts broke all over the world in January 2005 when Jennifer Aniston and Brad Pitt — the "It" couple of the '90s — announced they were divorcing after five years of marriage. Fast forward nearly two decades, and new fans are getting invested in their relationship all over again. You can thank Netflix for making their old-school projects like Friends more relevant then ever. Millennials are totally intrigued by what went down between Aniston and Pitt, why it was such a big deal, and where in the world the two stand nowadays. This timeline of Jennifer Aniston and Brad Pitt's relationship has seriously come full circle.
In the digital age, it's become so easy for celeb couples to publicly address their relationships through joint Instagram statements or subtle quotes posted to their Stories, but Pitt and Aniston's split happened in an entirely different time. In 2005, there was no social media to vent frustrations or subtweet on about your ex. All you had was official statements, paparazzi shots, and the tabloid press, which is why there's always been an air of mystery surrounding what happened between Aniston and Pitt. So here's a look back at their journey that'll take some of the mystery out of their rollercoaster relationship.
1998: A Classic Set Up
Aniston's whirlwind romance with Pitt all started thanks to a setup by their agents. "We both knew [we liked each other] on the first date," Aniston told Diane Sawyer in a 2004 interview. "It was weird... I thought, 'That's weird. That was a really easy evening. That was really fun.'" Watch her gush about Pitt in the clip below.
September 1999: Red Carpet Official
Less than a year after Aniston and Pitt went on their first date, the two made their red carpet debut at the 1999 Emmy Awards (looking '90s AF).
November 1999: Pitt Put A Ring On It
If you can't show off your brand new engagement ring on the 'Gram (because it's literally 1999), then crashing the stage at a packed Sting concert to show it off is definitely the next best thing. Aniston and Pitt stood front and center to share their news with the world.
July 2000: Wedding Of The Year
The moment fans had been waiting for arrived on July 29: Aniston and Pitt tied the knot in Malibu. The wedding was, of course, extravagant, but well hidden from the paparazzi. Photographers were only able to capture an aerial view of the celebration and a sky full of fireworks.
February 2003: She Won't Say She's In Love
When asked if Pitt was the love of her life during an interview with W magazine, Aniston's response made fans question everything they thought they knew about Brennifer.
“Is he the love of my life?" she mused. "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.'"
May 2004: Cheating Rumors Begin
Pitt and Angelina Jolie met and struck up a friendship on set of Mr. & Mrs. Smith. Their chemistry on screen and off was undeniable to fans, and gossip Pitt was cheating on Aniston with Jolie instantly began to swirl.
January 2005: Brennifer Is Officially Over
After months of tabloid rumors claiming Pitt was cheating on Aniston with Jolie, the actor and Aniston confirmed they were divorcing. “We would like to announce that after seven years together we have decided to formally separate," Aniston and Pitt shared in a statement to People Magazine.
They went on to deny any wrongdoing leading to the divorce, effectively shutting down cheating rumors. "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. We happily remain committed and caring friends with great love and admiration for one another.”
April 2005: Pitt And Jolie Vacation Together
While Pitt and Aniston's divorce statement stymied cheating rumors for a while, when photos of Pitt and Jolie vacationing in Kenya together surfaced online, the rumors came back with a vengeance.
Aniston spoke out about the hurt she endured after seeing the pictures in October 2006, telling Vanity Fair, "The world was shocked, and I was shocked.”
December 2008: Aniston Gets Real About Jolie And Pitt's Burgeoning Relationship
Pitt and Jolie were officially together, and Jolie wasn't shy about it. She even gushed about how she fell in love with Pitt on set of Mr. & Mrs. Smith to People — something Aniston was definitely not cool with.
"There was stuff printed there that was definitely from a time when I was unaware that it was happening," she told Vogue. "I felt those details were a little inappropriate to discuss. That stuff about how she couldn't wait to get to work every day? That was really uncool."
September 2011: Pitt Makes A Candid Confession
During an interview with Parade, Pitt gave some insight into what may have caused the downfall of his marriage to Aniston.
"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," he said. "I think that my marriage had something to do with it. Trying to pretend the marriage was something that it wasn’t.”
August 2014: Pitt And Jolie Tie The Knot
Pitt and Jolie officially wed in a private ceremony in Château Miraval, France after seven years together. They'd go on to have six children together.
August 2015: Aniston And Justin Theroux Get Hitched
One year after Pitt and Jolie tied the knot, Aniston wed Justin Theroux. The former couple said "I Do" in front of dozens of family and friends.
September 2016 & February 2018: Pitt & Aniston Divorce
Pitt and Jolie divorced in September 2016 after nine years together, and, just over a year later, Aniston called it quits with Theroux in February 2018. While Brangelina's split involved a messy custody battle, Aniston and Theroux's divorce was seemingly amicable.
"In an effort to reduce any further speculation, we have decided to announce our separation," the pair said in a joint statement to Us Weekly at the time. "This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship.”
February 2019: Pitt & Aniston Rekindle Their Friendship
Aniston threw an epic bash at the Sunset Towers in Hollywood to celebrate her 50th birthday, and single Pitt did not miss the opportunity to celebrate with his ex.
"The invite went out to a ton of people and he accepted," a source told Us Weekly, noting Aniston didn't make a big deal out of Pitt showing up. "She was happy he was there, but that was it. She was busy making the rounds and excited to see so many people near and dear to her.” Pitt and Aniston's teams did not respond to Elite Daily's request for confirmation of Us Weekly's report.
January 2020: Pitt Catches Aniston's Attention
Pitt and Aniston's first public display of post-divorce camaraderie came courtesy of the Golden Globes. When Pitt poked fun at his high-profile love life as he accepted the award for Best Supporting Actor in a Motion Picture for his role in Once Upon a Time in Hollywood, Aniston had the best reaction.
"I wanted to bring my mom, but I couldn’t because, any woman I stand next to, they say I’m dating… and it would just be awkward,” Pitt joked as the camera panned to Aniston cracking up knowingly.
So there you have it: They went from friends, to lovers, to exes, and back to friends. No one can tell the future, but fans are certainly hoping Brennifer's rekindled friendship turns into a rekindled romance.