Sinitta, 1984 – 1988. Bit of weird one this, but Brad honestly did date Louis Walsh's mate Sinitta on and off for four years. Fan of a palm leaf Sinitta dated Brad during her heady pop star days and he even attended the 1988 Smash Hits Poll Winners Party with her.
Robin Givens, 1986 – 1987. Yes, there is some overlapping with Sinitta. Very naughty, Brad…
The actor dated Mike Tyson's wife, while she was married to him. Very, VERY naughty, Brad.
Christina Applegate, 1989. The Don't Tell Mum The Babysitter's Dead star took Brad as her date to the MTV Movie Awards that year, only to famously ditch him halfway through the night for another guy. Burn.
Jill Schoelen, 1989. Brad and Jill met on the set of horror movie Cutting Class. He popped the question and they were engaged for three months in 1989, until she started dating the director of another movie she was working on, and dumped Brad. Burn Part II.
E.G. Daily, 1989. Brad dated E.G. Daily, a popstar, and more importantly the voice of Tommy Pickles in Rugrats and Phoebe's Smelly Cat nemesis in Friends, for a short time after Brad's split with Jill.
Juliette Lewis, 1989 – 1993. Brad was 27 when he started dating his 17-year-old Too Young To Die? co-star Juliette. She said in 2010 about the relationship: "It amazes me that people are still fascinated that we went out for four years. I was a teenager at the time. It's a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous."
Geena Davis, 1992. Yup, another overlap…
Apparently after starring alongside Geena in Thelma & Louise, Brad and Geena met up secretly in real life. That's according to Brad's former roommate Jason Priestly anyway.
Thandie Newton, 1994. Brad and Thandie dated briefly after they met on the set of Interview With The Vampire. They split amicably and are still friends apparently.
Gwyneth Paltrow, 1994 – 1997. Brad proposed to Gwyneth in 1996 after the couple met while filming Se7en two years earlier. Brad referred to Gwyn as his "angel" and "the love of his life" in his speech at the Golden Globes. They called off their engagement seven months after he proposed. Gwyn said in 2015: "I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt! My father was devastated [when we split]. I was such a kid, I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old. I wasn't ready, and he was too good for me."
Jennifer Aniston, 1998 – 2004. Brad and his first wife Jen met when their agents set them up on a blind date. After two years of dating, Brad and Jen got engaged, and started planning their lavish, Hollywood wedding, which took place on 29th July, 2001 in Malibu, and cost over $1million. Everything was fine until 2004 when Brad started filming Mr & Mrs Smith with Angelina Jolie. Nothing happened between Brad and Ange during filming, apparently, but Brad did say later on that it was during this time that he and Ange fell in love. In January 2005, Brad and Jen announced that they were getting divorced.
Angelina Jolie, 2004 – 2016. Brad and Angelina were together for 12 years, married for two and have six children together. Angelina filed for divorce from Brad on 19th September, 2016.
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