Despite enduring one of the most high-profile splits in Hollywood, Jennifer Aniston and Brad Pitt remain "buddies" over 15 years later.

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.

From their first date to their renewed friendship, here's a timeline of Jennifer Aniston and Brad Pitt's relationship.

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