There are few Hollywood couples as iconic as Jennifer Aniston and Brad Pitt. From a blind date in the late ’90s to a dream wedding, a devastating divorce and an unlikely friendship that endured it all, their story has everything. Here is a timeline of one of pop culture’s most iconic relationships.
1994 — The first meeting
It all started with a setup. Brad Pitt was first introduced to Jennifer Aniston in 1994 by their managers, as reported by Fox News. At the time both were on the rise. Aniston was becoming a household name through ‘Friends’ and Pitt was cementing his status as one of Hollywood’s most sought-after leading men with films like ‘Se7en’ and ‘Fight Club.’ However, despite meeting romance didn’t follow immediately. The two went their separate ways, each dating other people, and nothing came of that first encounter for several years.
1998 — The first date
Four years after initially crossing paths, Aniston and Pitt were both newly single and finally ready. Their agents set them up on a blind date in 1998 and by all accounts, the chemistry was instant. What started as a casual evening out quickly became something neither of them could ignore. Hollywood’s next great love story had officially begun.
November 1999 — The engagement
Just over a year into their relationship, Pitt popped the question. The couple announced their engagement while attending a Sting concert in November 1999, according to Rolling Stone. The news sent the press into overdrive and fans into a frenzy. The world’s two most glamorous people were going to get married and everyone wanted a front-row seat.
2000 — The wedding of the decade
In July 2000, Jennifer Aniston and Brad Pitt married in a lavish beachside ceremony in Malibu, California. Marie Claire described it as a celebration complete with caviar and musical performances, an event people still reference decades later. They were not just a couple, they were a cultural institution. Their red carpet appearances, their coordinated style, their easy affection in public, all of it made them the couple everyone aspired to be.
2004 — Talk of a family and the cracks begin
In 2004, Aniston spoke openly about her desire to start a family, telling The Guardian, “It’s time. It’s time. You know, I think you can work with a baby, I think you can work pregnant, I think you can do all of it. So, I’m just truly looking forward to slowing down.” It sounded like the next beautiful chapter was just around the corner. But that same year, Pitt began filming ‘Mr. and Mrs. Smith’ alongside Angelina Jolie and everything changed.
2005 — The divorce that shook Hollywood
Rumours of an affair between Pitt and his co-star Jolie spread rapidly, and the speculation proved to be well-founded. Jolie later confirmed that she and Pitt had fallen in love on set. Aniston filed for divorce in March 2005, and it was finalised seven months later. In a deeply personal interview with Vanity Fair shortly after, Aniston spoke about the pain of going through such a public unravelling. “It’s sad, something coming to an end. It cracks you open, in a way, cracks you open to feeling,” she said. “When you try to avoid the pain, it creates greater pain. I’m a human being, having a human experience in front of the world. I wish it weren’t in front of the world. I try really hard to rise above it.”Pitt and Jolie went on to date, start a family and raise their six chidren for nearly a decade before marrying in 2014, then separating in 2016.
2019 – Brad and Jennifer reconnect
While the public assumed Aniston and Pitt had little to no contact after the divorce, the reality was far more nuanced. Pitt quietly attended Aniston’s annual holiday parties over the years, and in a detail that slipped out almost by accident, he was reportedly present at her 50th birthday party in February 2019. Aniston’s ‘Morning Show’ co-star Reese Witherspoon accidentally revealed this on the Armchair Expert podcast, saying, “At her 50th birthday, one of the biggest testaments I can say to what a wonderful person she is, people from her teenage years, people from her 20s, people who work in her home, every ex-husband, ex-boyfriend was there.” Every ex-husband. The internet connected the dots immediately.
January 2020 — The Award moment that broke the internet
Nothing, however, compared to the moment at the 26th Annual Screen Actors Guild Awards in January 2020. Both Aniston and Pitt were nominated that night, she for ‘The Morning Show’ and he for ‘Once Upon a Time in Hollywood.’ Pitt won his award and gave a speech that had the room in stitches, joking about his character “who doesn’t get on with his wife.” Cameras immediately cut to Aniston in the audience, who smiled and applauded. Then, backstage, the two ran into each other and shared a moment that was photographed and instantly became one of the most iconic moments in Hollywood history.Ahead of the ceremony, Pitt had been asked by Entertainment Tonight whether he would welcome running into his ex. His answer was simple: “I’ll run into Jen. She’s a good friend.”
2020 – Brad and Jennifer reunite for a script read
At a time when reconciliation buzz was floating around social media, the two reunited virtually for a table read of ‘Fast Times at Ridgemont High’ to support a nonprofit. Sitting side by side on screen and giggling as they read the naughty dialogues, the two sent fans on the internet into a spiral. Shortly after, Aniston appeared on The Howard Stern Show and put the speculation to rest once and for all, confirming that she and Brad are genuinely on good terms.
2025 – Aniston opens up about ‘love triangle’
For years, Aniston largely stayed quiet about the specifics of the betrayal. But in August 2025, she finally addressed what she called the “love triangle” that had defined so much tabloid coverage of her life. Speaking to Parade, she said, “It was such juicy reading for people. If they didn’t have their soap operas, they had their tabloids.” She did not hold back on acknowledging how painful the period was, adding, “It was also such a vulnerable time. But yeah, that was one for the memoirs.” She also notably told one interviewer at the time that her ex had a “sensitivity chip missing,” a line that stuck with people for years.
Where they stand today
Today, both have moved on in their personal and professional lives. Pitt has been in a steady relationship with Ines de Ramon since late 2022. Jen, on the other hand, has been dating Jim Curtis, since 2025.
