Brad Pitt seems pretty happy these days with his partner Ines de Ramon but if you've followed Hollywood over the years and his dating history has always been a hot topic.
Back in the late 1980s, before he was a household name Brad dated singer Sinitta and had short flings with actors like Shalane McCall, Robin Givens and Christina Applegate.
He even got engaged to his Cutting Class co-star Jill Schoelen though that ended quickly after she broke things off during a movie shoot in Budapest.
By the 1990s, Brad was becoming a major star. He dated Juliette Lewis for a few years after starring together in two films and later fell for Gwyneth Paltrow on the set of Se7en in 1995.
The two were one of the biggest celebrity couples of the decade and even got engaged before calling it quits in 1997.
Then came the iconic marriage. Brad met Friends star Jennifer Aniston on a blind date in 1998 and they married in 2000. They instantly became Hollywood’s favorite golden couple but after five years of marriage, they announced their separation in early 2005.
Shortly after, Brad began dating his Mr. & Mrs. Smith co-star Angelina Jolie. Dubbed "Brangelina" by fans and the pair spent over a decade together also raised six kids and officially married in 2014. However Jolie filed for divorce in 2016 with kicking off a long legal battle that finally settled in late 2024.
Fast forward to today, Brad has settled down again with jewelry executive Ines de Ramon.
The two were first spotted together in late 2022 and made things official on social media in mid-2026, opening a calm new chapter in the Oscar winner's love life.
