Despite going through one of Hollywood’s most publicized breakups, Jennifer Aniston and Brad Pitt have remained friendly more than 15 years later. The two actors met through their managers and secretly dated before making their relationship public.
They got married in a grand ceremony in 2000 but decided to separate in 2005. After their split, Pitt married Angelina Jolie, his co-star from “Mr. & Mrs. Smith,” while Aniston tied the knot with actor Justin Theroux.
Aniston expressed her feelings about Pitt in an interview with Vanity Fair, saying, “I really do hope that someday we can be friends again. I will love [Brad] for the rest of my life. He’s a fantastic man.
I don’t regret any of it, and I’m not going to beat myself up about it.” In recent years, their friendship has appeared to grow stronger. Fans were thrilled when the two had not just one but two reunions in 2020.
Their warm backstage embrace at the SAG Awards quickly went viral, and later that year, they participated in a virtual table reading of “Fast Times at Ridgemont High.”
Here is a timeline of Jennifer Aniston and Brad Pitt’s relationship, from their first meeting to their current friendship.
1994: Jennifer Aniston and Brad Pitt Meet for the First Time
In the mid-’90s, their managers introduced them to each other. Aniston later described Pitt to Rolling Stone, saying, “He was just this sweet guy from Missouri, you know? A normal guy.”
1998: Jennifer Aniston and Brad Pitt Go on Their First Date
At the time, both actors were newly single. Aniston had ended her relationship with actor Tate Donovan, and Pitt had recently broken off his engagement to Gwyneth Paltrow.
Their managers arranged for them to meet again, and this time, they clicked instantly. “That was a really easy evening. It was really fun,” Aniston told Diane Sawyer when describing their first date.
September 12, 1999: Red Carpet Debut
The couple kept their relationship private in the beginning. However, they made a big statement when they stepped onto the red carpet together at the 1999 Emmy Awards. Pitt sported silver sunglasses, while Aniston shined in a sequined dress.
November 21, 1999: Engagement Announcement
During a Sting concert in New York City, the couple surprised the audience by announcing their engagement.
Aniston showed off a stunning diamond-and-platinum engagement ring designed by Italian jeweler Silvia Damiani. Reports later revealed that Pitt spent seven months working on the ring’s design.
July 29, 2000: Wedding Day
The couple exchanged vows in Malibu, California, in the presence of 200 friends, family members, and fellow actors. Aniston made a sweet promise in her vows, saying she would always make Pitt’s “favorite banana milkshake.”
The grand wedding included 50,000 flowers, live music from four bands, a fireworks display, and more. The event was estimated to have cost around $1 million.
September 10, 2000: First Red Carpet Appearance as a Married Couple
One year after their red carpet debut, the newlyweds attended the 2000 Emmy Awards together, captivating the crowd once again.
November 2001: Brad Pitt Guest Stars on “Friends”
Pitt joined Aniston on her hit TV show “Friends,” making an appearance in the Thanksgiving episode of season 8 titled “The One with the Rumor.”
He played Will Colbert, a character who disliked Rachel Green, the role played by Aniston. She later revealed that Pitt was one of her favorite guest stars, saying, “Mr. Pitt was wonderful.”
Jennifer Aniston And Brad Pitt (Credit: Getty Images)2002: The Couple Launches Plan B Entertainment
Aniston and Pitt co-founded Plan B Entertainment along with producer Brad Grey. Aniston explained in an interview with The Guardian that they wanted to build something meaningful.
“We started this little company underground, didn’t really talk about it because we didn’t want to be accused of being actors who have vanity deals where you don’t do anything.” Pitt eventually became the sole owner of the company after their separation.
February 2003: Jennifer Aniston Reflects on Their Relationship
In an interview with W Magazine, Aniston was asked if Pitt was the love of her life. She gave a thoughtful response: “Is he the love of my life?
I think you’re always sort of wondering. 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.” She emphasized that they shared something special.
February 2004: Jennifer Aniston Talks About Starting a Family
Aniston told The Guardian that she was ready to start a family with Pitt. “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.”
January 7, 2005: The Couple Announces Their Separation
After spending New Year’s Eve together in Anguilla, Aniston and Pitt shared a statement announcing their decision to separate. They emphasized that their breakup was not due to media speculation and that they remained “committed and caring friends.”
March 25, 2005: Jennifer Aniston Files for Divorce
Aniston officially filed for divorce in Los Angeles, citing irreconcilable differences. She also requested to legally restore her last name to Aniston. Their divorce was finalized on October 2 of that year.
September 2005: Jennifer Aniston Speaks About the Breakup
Aniston gave an interview to Vanity Fair, discussing the emotional impact of the split. She acknowledged that she had gone through different stages of grief and expressed her frustration with how the media portrayed her.
She stated, “I would much rather everyone move on. I am not defined by this relationship.”
September 2011: Brad Pitt Clarifies His Comments on Their Marriage
In an interview with Parade, Pitt said he was trying to find meaning in his life during their marriage but later clarified his remarks.
He insisted that Aniston was a wonderful person and that his words were misinterpreted. “Jen is an incredibly giving, loving, and hilarious woman who remains my friend.”
August 2014 – August 2015: Both Actors Remarry
Pitt married Angelina Jolie in a private ceremony in France, while Aniston married Justin Theroux in a surprise event at their Bel Air home.
February 2018: Jennifer Aniston and Justin Theroux Separate
After nearly three years of marriage, Aniston and Theroux decided to part ways. Their statement emphasized that they remained close friends.
February 9, 2019: Brad Pitt Attends Jennifer Aniston’s 50th Birthday Party
Pitt was seen at Aniston’s birthday celebration in Hollywood, showing that their friendship remained strong.
January 19, 2020: Jennifer Aniston and Brad Pitt’s Reunion at the SAG Awards
Fans were delighted when Aniston and Pitt shared a warm moment backstage at the SAG Awards. The interaction sparked speculation, but sources stated that they were just happy for each other’s success.
September 18, 2020: Virtual Table Read for Charity
Pitt and Aniston reunited for a virtual table read of “Fast Times at Ridgemont High.” Their playful exchange was a highlight of the event, bringing laughter to their fellow cast members.
June 23, 2021: Jennifer Aniston Confirms Their Friendship
Aniston assured fans that she and Pitt were good friends. “Brad and I are buddies, we’re friends,” she said during an interview. “We had fun, and it was for a great cause.”