Mens Upflow but I couldn’t because anyone I stand next to they say I’m dating,” he teased in his speech. “It’d just be awkward.” Read more Brad Pitt reveals he hasn’t cried in almost 20 years Pitt has had two very public breakups over the course of his career. In 2005, he split from Jennifer Aniston after five years of marriage, citing irreconcilable differences. The actor famously then dated Angelina Jolie after the two met on the set of Mr and Mrs Smith, which they started filming in 2004. Pitt and Jolie married in 2014 but separated in 2016. The couple have six children together, three of whom are adopted. Their divorce was finalised in April 2019. The Independent's Millennial Love group is the best place to discuss to the highs and lows of modern dating and relationships. Join the conversation here. .