The actors were introduced by their managers and secretly dated before tying the knot in a lavish 2000 ceremony. Ultimately, they called it quits in 2005 and went on to wed other people, Pitt to his Mr. & Mrs. Smith costar Angelina Jolie and Aniston to actor Justin Theroux.
“I really do hope that someday we can be friends again,” Aniston told Vanity Fair in the wake of their split. “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,” she continued.
In recent years, the former pair have appeared to rekindle their friendship, delighting fans with not one, but two reunions in 2020: a warm backstage embrace at the SAG Awards that quickly went viral and a virtual table reading of Fast Times at Ridgemont High.
1994: Jennifer Aniston and Brad Pitt first meet
Aniston and Pitt were introduced by their managers in the mid-’90s, years before their relationship turned romantic. “He was just this sweet guy from Missouri, you know?” Aniston later recounted to Rolling Stone of her first impression of her future husband. “A normal guy.”
1998: Jennifer Aniston and Brad Pitt go on their first date
With both Aniston and Pitt newly single — she split from actor Tate Donovan and he recently called off his engagement to Gwyneth Paltrow — their managers brought them together once again. This time, they hit it off.
“That was a really easy evening. It was really fun,” Aniston later told Diane Sawyer of their immediate chemistry.
September 12, 1999: Jennifer Aniston and Brad Pitt make their red carpet debut
The couple kept their romance under wraps for the first few months, before making their highly-anticipated red carpet debut at the 1999 Emmy Awards. The duo hit the carpet in particularly memorable looks, with Pitt wearing a pair of silver sunglasses and Aniston in a sequined dress.
November 21, 1999: Jennifer Aniston and Brad Pitt announce their engagement
During a Sting concert at New York City’s Beacon Theater, the couple took the stage to show off Aniston’s new bling: a diamond-and-platinum engagement ring from Italian jewelry designer Silvia Damiani, which PEOPLE reported that Pitt spent seven months helping design.
July 29, 2000: Jennifer Aniston and Brad Pitt get married
Surrounded by 200 of their friends, family and costars, the couple exchanged heartfelt vows — with Aniston promising to always make Pitt’s “favorite banana milk shake” — beside the beach in Malibu, California. The lavish nuptials featured 50,000 flowers, four bands, a 13-minute fireworks display and more. The bride wore a silk-and-satin…