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 Paltrow began dating in 1994 before getting engaged two years later. They called it quits before making it down the aisle.