Getty Images
Getty Images

Brad Pitt and Jennifer Aniston's Relationship Timeline: How They Met, When They Went Public & When It All Ended

Pedro Marrero
Dec 20, 2019
01:03 P.M.

The two met as young aspiring actors that were just about to make it in show business, but by the time when rumors about their romance started to spread, they were two A-list celebrities in an iconic Hollywood love story.


What started as another Hollywood fairytale and was made official by marriage, ended up in a negative note when a third party became involved. But 20 years since Brad Pitt and Jennifer Aniston made their relationship public, another chapter might be starting for these two.

Ever since Pitt effectively parted ways with his former wife Angelina Jolie, finalizing their divorce in 2019, there have been insisting rumors about Pitt and Jolie getting back together. (There is nothing confirmed on this matter as of December 19).

Brad Pitt and Jennifer Aniston. I Image: Getty Images.

Brad Pitt and Jennifer Aniston. I Image: Getty Images.


With this in mind, let’s take a look back in time to revisit the love story between two of the biggest stars to come out of the ‘90s.


Pitt and Aniston first met casually in 1994, when “Friends” was about to become a cultural phenomenon, launching Aniston to superstardom, and Pitt was building a big screen reputation with roles in “Interview with the Vampire” and “Seven.”

The two performers had a manager in common, and Aniston recalled how ordinary Pitt seemed to her back then. “He was just this sweet guy from Missouri, you know? A normal guy,” Aniston said about her first impression of the actor.

Brad Pitt and Jennifer Aniston. I Image: Getty Images.

Brad Pitt and Jennifer Aniston. I Image: Getty Images.

Nothing worthy of mention happened between the two at that moment, when Pitt was dating Gwyneth Paltrow and Aniston was in a relationship with Tate Donovan.



In 1998, as it only happens in Hollywood, Pitt and Aniston went on their first date, set up by their manager after the two had ended their previous relationships.

Whoever had the idea of pairing them really had a vision, for after that practically blind date, as Aniston shared with Diane Sawyer later, the two actually felt a strong connection since day one.

Jennifer Aniston and Brad Pitt. I Image: Getty Images.

Jennifer Aniston and Brad Pitt. I Image: Getty Images.


“We both [knew] on our first date. It was weird… That was a really easy evening. It was really fun,” Aniston recalled in 2004.


After a brief moment of the awkwardness out of nerves on which Aniston didn’t return Pitt’s calls, the two entered into a relationship, and they tried in vain to keep things under wraps for a while before facing public scrutiny.

Jennifer Aniston and Brad Pitt. I Image: Getty Images.

Jennifer Aniston and Brad Pitt. I Image: Getty Images.


It was hard for them to surf their busy schedules and use any free time to spend time together, and it later surfaced that Pitt secretly traveled to Texas to accompany Aniston as she filmed “Office Space.”

According to Aniston former co-star in the comedy film, Greg Pitts, Aniston stayed in a different hotel than the rest of the cast, where she could meet with Pitt in private, but, apparently, they weren’t fooling anyone, and there was already a hunt for a picture of the two together.


After testing the grounds with their inner circle of friends, with Pitt throwing a 30th birthday party for Aniston at Sunset Boulevard in February 1999, and taking a romantic trip to Acapulco to think things over, they were ready to open up.

Jennifer Aniston and Brad Pitt. I Image: Getty Images.

Jennifer Aniston and Brad Pitt. I Image: Getty Images.

Later that year, the couple used the Emmy Awards red carpet as a setting for their first official public outing as an item. Not much later, in September, Aniston and Pitt delighted their fans with the news of their engagement, during a Sting concert.



Late in July 2000, Aniston, then 31, and Pitt, then 36, exchanged vows in a lavish ceremony. The much-anticipated wedding, celebrated in Malibu, California, with about 200 lucky guests, didn’t disappoint.

People reported at the time, the occasion was marked with 50,000 flowers, four bands, a gospel choir, and fireworks. Aniston was escorted down the aisle by her father, “Days of Our Lives” actor John Aniston.


Jennifer’s “Friends” co-stars Courteney Cox, David Schwimmer, Matthew Perry, and Lisa Kudrow, were in attendance. Pitt’s “Fight Club” co-star Edward Norton, with his girlfriend of that time, Salma Hayek, also graced the party with their presence.


In 2001, the happy newlyweds famously shared the screen during an episode of “Friends” titled “The One with the Rumor,” on which Pitt guest-starred as Rachel’s former classmate who secretly hates her and wants to take revenge.

Early in 2003, Aniston raised concerns when she admitted that she wasn’t sure about Pitt being the love of her life, but by the next year, she shared that she felt the time was right for the two to start a family.


But soon, Aniston’s plans were about to change when Pitt started to shoot “Mr. and Mrs. Smith” opposing Jolie in May 2004, and soon, the chemistry between the two co-stars sparked rumors of an extra-marital affair.


Even though Pitt didn’t admit to having indulged in infidelity with Jolie at the time (the two later admitted to having fallen in love on set), by January 2005, Pitt and Aniston’s marriage had collapsed, forcing them to announce their separation.

Later that year, Aniston addressed the breakup in public for the first time, and she insisted that the rumors about cheating were not true, claiming that the two “exited this relationship as beautifully as [they] entered it.”

In October 2005, Aniston and Pitt finalized their divorce after four years of marriage, citing irreconcilable differences.

Please fill in your e-mail so we can share with you our top stories!
By subscribing, you agree to our Privacy Policy
Related posts

Jennifer Aniston's Relationship with Her Mom Left 'Deep Wounds' & Resulted in a 15-Year Estrangement

January 24, 2023

Gwyneth Paltrow's Father Loved Her Fiancé Brad Pitt 'Like a Son' —She Felt Responsible for Their Break Up

April 30, 2022

Sandra Bullock Had 'One Great Love in Life' Who She 'Chased like a Dog' & Prioritized over Herself

April 10, 2022

Mindy Cohn’s World Now after She Suddenly Felt Exhausted & Had to Fight for Her Life for 5 Years against Cancer

March 29, 2022

Angelina Jolie & Brad Pitt's Tomboy Daughter Shiloh Is Now an Exquisite Style Icon

May 21, 2022

'I Can't Believe I Actually Found You!': Birth Mom Reunites with Son after 33 Years of Separation

March 05, 2022

Laura Dern Was Dumped by Men She Loved Twice - Angelina Jolie Stole Her Fiancé While She Was on Set

February 15, 2022

Adam Sandler ‘Locked Eyes & Fell Deep’ for a Girl Serving Drinks in His Film - They Are Together for 24 Years

February 07, 2022

Ben Affleck Returned J Lo's 'Happiest Times' after Love Fails & Proposed with Bigger Ring than in 2002

April 11, 2022

Julia Roberts & Lyle Lovett’s Marriage Was like ‘One Giant Honeymoon’ – Inside the Controversial Romance

February 10, 2022

Angelina Jolie Visited Children in Ukraine - Meet Her Grown up Children

May 02, 2022

Pink Once Invited Husband to Her Room and Gifted Him a Photo Album That Included Divorce Papers

March 14, 2022

Jennifer Grey Was Married to Clark Gregg for 19 Years and Share a Child — She Cried When They Separated

February 06, 2022

Is Channing Tatum Married? Inside the Private Life of 'The Lost City' Star

May 11, 2022