In the late 1980s and 1990s, Pitt dated several of his co-stars, including Robin Givens (Head Of The Class), Jill Schoelen (Cutting Class), Juliette Lewis (Too Young to Die? and Kalifornia), who at sixteen was ten years his junior when they started dating, and Gwyneth Paltrow (Se7en), with whom he had a much-publicized engagement. Pitt also dated actresses Sinitta and Thandie Newton.

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Pitt met Friends actress Jennifer Aniston in 1998 and married her during an enclosed wedding ceremony in Malibu on July 29, 2000. The couple ensured that the ceremony would be a private affair by hiring hundreds of guards to block any attempts of invasion by the paparazzi; just one wedding picture was released to the media. Not long after the wedding, Pitt sued Damiani International, the company Read more...

One month after Aniston filed for divorce, in April 2005, a set of paparazzi photos emerged that seemed to confirm the rumors of a relationship between Pitt and actress Angelina Jolie. The photos, which were reportedly sold for $500,000, showed Pitt, Jolie and her son Maddox at a beach in Kenya. During the summer, the pair were seen together with increasing frequency, and the entertainment media Read more...