Shortly after Gwyneth and Brad called off their engagement, he famously began dating Jennifer Aniston. Of course, it wasn’t long before Brad and Jen were engaged, and by the year 2000, they were married. Their marriage was ultimately short-lived, with the pair announcing their separation early in 2005.

Pitt and Aniston met in 1998 after being set up on a blind date by their agents. The two tied the knot by 2000 before splitting five years later.