There are few iconic couples in Hollywood 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, their story has it all. Here’s a timeline of one of pop culture’s most iconic relationships.
1994 — First meeting
It all started with a setup. Brad Pitt was first introduced to Jennifer Aniston by their managers in 1994, Fox News reported. Both were on the rise at the time. Aniston was becoming a household name through ‘Friends’ and Pitt was cementing himself as one of Hollywood’s leading men with films like ‘Se7en’ and ‘Fight Club’. However, despite meeting the romance did not immediately follow. The two went their separate ways, each contacted other people, and nothing happened after that first meeting for several years.
1998 — First date
Four years after they first crossed paths, Aniston and Pitt were newly single and finally ready. Their agents set them up on a blind date in 1998 and anyway, the chemistry was instant. What started as a casual evening quickly turned into something neither of them could ignore. Hollywood’s next great love story has officially begun.
November 1999 — Commitment
A little over a year into their relationship, Pitt popped the question. The couple announced their engagement at a wedding Sting concert in November 1999, according to Rolling Stone. The news sent the press into overdrive and fans into a frenzy. The two most fascinating people in the world were about 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 ceremony on the beach in Malibu, California. Marie Claire described it as a celebration complete with caviar and musical performances, an event that people still refer to decades later. They were not just a couple, they were a cultural institution. Their red carpet appearances, their coordinated style, their easy love in public made them the couple everyone wanted to be.
2004 — Talk about a family and the cracks begin
In 2004, Aniston spoke openly about her desire to start a family, telling The Guardian: “It’s about 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 everything. So I’m really trying to slow down.” It seemed like the next beautiful chapter was just around the corner. But that same year, Pitt started filming ‘Mr. and Mrs. Smith’ with Angelina Jolie and everything changed.
2005 – The divorce that shook Hollywood
Rumors of an affair between Pitt and his co-star Jolie quickly spread, and the speculation was well-founded. Jolie later confirmed that she and Pitt fell in love on set. Aniston filed for divorce in March 2005, which was finalized seven months later. In a very personal interview with Vanity Fair shortly after, Aniston spoke about the pain of going through such a public appearance. “It’s sad, something is coming to an end. It kind of opens you up, opens you up to the feeling,” he said. “When you try to avoid the pain, it creates more pain. I am a human being living a human experience in front of the world. I wish I wasn’t in front of the world. I try very hard to rise above him.’Pitt and Jolie dated, started a family and raised their six children for nearly a decade before marrying in 2014 and splitting in 2016.
2019 – Brad and Jennifer reconnect
Although the public believed that Aniston and Pitt had little contact after the divorce, the reality was much more nuanced. Pitt has been quietly attending Aniston’s annual holiday parties, and in one detail he almost accidentally slipped up, he reportedly attended her 50th birthday party in February 2019. Aniston’s ‘Morning Show’ co-host Reese Witherspoon revealed this unexpectedly on the Armchair Expert podcast, saying: “For her 50th birthday, one of the biggest testaments I can say to what a wonderful person she is, the people from her teenage years, the people in her 20s, the people who work at her house, all her ex-husbands were there, among other things.” Every ex-husband. The Internet immediately connected the dots.
January 2020 – The award moment that broke the internet
Nothing, though, compared to the moment at the 26th Annual Screen Actors Guild Awards in January 2020. That night Aniston and Pitt were nominated, she for ‘The Morning Show’ and he for ‘Once Upon a Time in Hollywood’. Pitt won his award and delivered a packed speech, joking about his character “not getting along with his wife”. The cameras immediately cut to Aniston in the audience, who smiled and applauded. Then, backstage, the two bumped into each other and shared a photo that instantly became one of the most iconic moments in Hollywood history.Before the event, Pitt was asked by Entertainment Tonight if he would be okay with running into his ex. His answer was simple: “I’ll meet Jen. She’s a good friend.”
2020 – Brad and Jennifer met to read the script
Amid social media buzz of a reconciliation, the two almost reunited for a reading of “Fast Times at Ridgemont High” to support a nonprofit. Sitting next to each other on screen and giggling as they read naughty conversations, the two sent internet fans 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 indeed on good terms.
2025 – Aniston talks about “love triangle”.
For many years, Aniston remained silent about the specifics of the betrayal. But in August 2025, she finally came to grips with what she called the “love triangle” that defined so much tabloid coverage of her life. Speaking to Parade, he said: “It was a juicy read for people. If they didn’t have their soap operas, they had their tabloids.” He couldn’t resist acknowledging how painful the period was, adding: “It was also such a vulnerable time. But yeah, that was one for the memories.” She also told an interviewer at the time that her ex lacked “a chip of sensitivity,” a line that stuck with people for years.
Where are they now?
Today, both have progressed in their personal and professional lives. Pitt has been in a steady relationship with Ines de Ramon since the end of 2022. Jen, on the other hand, has been dating Jim Curtis since 2025.
