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Slide 14 of 19

Jennifer Aniston

Pitt and Aniston reportedly met in 1998 after their respective agents set them up on a blind date. The Hollywood golden couple continued to date for two more years before Pitt popped the question, and they had a lavish, million-dollar wedding in Malibu. In 2004, Pitt started shooting "Mr. and Mrs. Smith" with Angelina Jolie after Nicole Kidman pulled out of the film. This, combined with reports of Aniston not wanting to have kids, led to nonstop rumours about the couple. She filed for divorce in 2004 after four-and-a-half years of marriage, and Pitt went on to marry Jolie.

Image Source: Getty / Evan Agostini