We may receive a commission on purchases made from links.

In one of Hollywood's biggest what ifs, Gwyneth Paltrow was once engaged to be married to Brad Pitt. It wasn't meant to be, however, with the "Shakespeare in Love" star reportedly breaking things off. She and Pitt were eventually able to mend fences, forming a friendship that even Paltrow's current husband Brad Falchuk approves of . That said, things were still pretty tense in the immediate aftermath of the A-listers' 1997 breakup, particularly once Pitt married "Friends" star Jennifer Aniston in 2000. In fact, despite the fact that Paltrow blames herself for her split from Pitt , the Oscar winner apparently threw some serious shade at her ex and his new wife back in the day.

In Amy Odell's book "Gwyneth: The Biography," the

See Full Page