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.

Gwyneth Paltrow felt Brad Pitt didn't match up to her standards of sophistication, according to the latest bombshell claim from a new book about the actress.