Brad Pitt’s Dating History Is Full of Famous Faces

Brad Pitt is currently one of the most eligible bachelors in Hollywood. But during his 30+ year career, he’s been linked to numerous beautiful women. There was actually a time when the Oscar winner was in a relationship with someone other than Angelina Jolie or Jennifer Aniston! Let’s take a look at Pitt’s dating history, which is full of famous faces.

Brad Pitt and Gwyneth Paltrow at The Ivy restaurant, London, 14th August 1995.
Brad Pitt and Gwyneth Paltrow | Dave Benett/Hulton Archive/Getty Images

Brad Pitt was briefly engaged in the late 1980s to his ‘Cutting Class’ co-star Jill Schoelen

Before Pitt broke into Hollywood and started getting TV and movie roles, he dated British singer Sinitta between 1984 and 1986. During her appearance on I’m A Celebrity in the UK, Sinitta had nothing but praise for the Fight Club star.

“[He was] hot. He was beautiful with the most amazing body. I saw him for two years,” Sinitta said, per Cosmo. “He was fun, he was young and very sweet. It was before he made Thelma & Louise, but even I saw that movie and thought, ‘Oh my god, what have I done?’”

Pitt’s first major film role was in 1989’s direct-to-video slasher film Cutting Class, starring scream queen Jill Schoelen. Pitt and Schoelen started dating during filming and then he quickly popped the question. The couple was engaged for eight months before they called off their wedding and split.

Christina Applegate dumped him mid-date

After his break-up with Schoelen, Pitt briefly dated Married…With Children star Christina Applegate. However, when they were at the 1989 MTV Video Music Awards, Applegate dumped Pitt mid-date for another guy. 

During an appearance on Watch What Happens Live, Applegate refused to name the man she left Pitt for. But she did say that he was not an actor — implying he was a famous musician. 

A year later, Pitt met Juliette Lewis on the set of the 1990 TV movie Too Young to Die?. At the time, he was 26 and she was 17. Needless to say, the relationship didn’t last.

“It amazes me that people are still fascinated that we went out for 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,” Lewis later said.

Brad Pitt loves to date his co-stars

In 1994, Pitt once again fell for one of his co-stars when he started dating Thandiwe Newton, after meeting her on the set of Interview With a Vampire. Their low-key relationship lasted about a year. 

Then, Pitt started dating Gwyneth Paltrow — and things got super serious. He even thanked her at the 1996 Golden Globes while accepting his award for Best Supporting Actor. Later that year, they got engaged. 

“I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!” the Goop founder said. “My father was devastated [when we broke up]. 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.”

In 1998, Pitt briefly dated his Meet Joe Black co-star Claire Forlani. And later that year, his agent set him up with Jennifer Aniston. Of course, they got married and were together for more than five years — until he starred alongside Jolie in Mr. & Mrs. Smith.

Pitt and Jolie were together for 11 years and married for two. She filed for divorce in 2016, and the former couple is still fighting in court over the custody of their six children. Since Pitt’s divorce, he’s only been linked to model Nicole Poturalski. But they were only together for two months before calling it quits.

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