The year that Jennifer Aniston landed the role of a soon-to-be ex in The Break-Up, she was going through the same thing in real life. She and then-husband Brad Pitt announced their separation in 2005 amidst infidelity rumors about Pitt allegedly dating his Mr.

Brad Pitt's relationships with Jennifer Aniston and Gwyneth Paltrow may not have worked out, but the two ladies ended up finding friendship with each other. Aniston, who was married to Pitt from 2000-2005, opened up about her unlikely bond with Paltrow, who dated and was once engaged to Pitt in the '90s, in a new interview with Vanity Fair.