Brad Pitt’s Dating History: A Timeline of His Famous Flings

(Photo by Lawrence Schwartzwald/Sygma via Getty Images)

Brad Pitt is one of Hollywood’s most iconic actors, and the star has had a long list of former flames during his time in the spotlight. With more than 30 years as an actor, Brad Pitt has spent more than three decades dating women in Hollywood, including a few superstars such as Jennifer Aniston and Angelina Jolie. While you may think you know everyone that Brad Pitt has dated, you might be surprised to learn about some of his famous flings from his earlier years of dating. If you’re a fan of the handsome and charming Brad Pitt, follow along as we retrace his dating history back to his early years in Hollywood.

Sinitta

One of Pitt’s earliest relationships was with British singer Sinitta, best known for the song “So Macho” and appearances on shows such as I’m a Celebrity…Get Me Out of Here. The pair dated on and off for two years between 1986 and 1988, which was before Pitt’s fame skyrocketed after Thelma & Louise. Sinitta opened up about her romance with Pitt while she was on I’m a Celebrity: “[He was] hot. He was beautiful with the most amazing body. I saw him for two years,” Sinitta said at the time. “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?’”

(Photo by Mike Marsland/Mike Marsland/WireImage)

Shalane McCall

Brad Pitt and Shalane McCall were rumored to have dated on and off between 1987 and 1988. Pitt starred in four episodes of Dallas as McCall’s boyfriend at the time, and it was rumored that the pair had taken their romance off-screen. McCall was reportedly Pitt’s first onscreen kiss, but their relationship didn’t progress much after Pitt left the show. McCall quickly moved on following the rumored romance and tied the knot with Trent Valladares in 1999.

(Photo by Jim Smeal/Ron Galella Collection via Getty Images)

Jill Schoelen

One significant relationship of Pitt’s that many may forget about, or not know about at all, is his relationship with Jill Schoelen. The two were actually engaged for eight months in 1989. They met while starring together as costars in Cutting Class, but they called their engagement off when Pitt went to visit Schoelen while she was on-set in Budapest, Hungary. In 2011, Pitt reportedly opened up about the relationship and revealed: “She told me that she had fallen in love with the director of the film. I was so shocked I said, ‘I’m outta here.'”

(Photo by Barry King/WireImage)

Christina Applegate

Another one of Pitt’s famous relationships that many may forget about is when he dated actress Christina Applegate. While the two didn’t date for long, Pitt did attend the 1989 MTV Video Music Awards as Applegate’s date. Famously, Applegate ditched Pitt on the night of the MTV Awards for another man. In 2015, Applegate confirmed to Andy Cohen that this story did, in fact, take place, but she did not confirm who she left him for. She did share with Cohen that the person was not an actor, and many have speculated that the mystery man was singer Sebastian Bach.

(Photo by Jeff Kravitz/FilmMagic)

E.G. Daily

One year after his engagement ended with Schoelen, Pitt moved on to PeeWee’s Big Adventure star E.G. Daily. The couple reportedly ended their romantic relationship in 1988, but the two remained friends. Reports have revealed that E.G. helped to console a heartbroken Pitt following the end of his engagement. E.G. opened up about her relationship with Pitt in True Hollywood Story: “I think he was really intense about his work,” E.G. explained. “When you saw him, it was more like seething in him underneath. What I could feel from him was a really strong, visceral drive towards something really big.”

(Photo by Barry King/WireImage)

Juliette Lewis

Brad Pitt and Juliette Lewis began dating after meeting on the set of Too Young to Die in 1990. The pair went on to date for three years and reunited on the 1993 film, Kalifornia. Lewis opened up about their relationship while promoting the film: “We’re at the point in love, where we just like to see each other every single day and we don’t get bored with each other, so it’s really, really nice.” Years later, Lewis opened up about the relationship again in a 2010 interview: “It amazes me that people are still fascinated that we went out for years,” she said at the time. “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.”

(Photo by Jeff Kravitz/FilmMagic, Inc)

Geena Davis

In 1991, Brad Pitt made an appearance in Thelma & Louise that skyrocketed his fame and changed everything. Pitt played the character JD, a young drifter who Thelma, played by Geena Davis, falls for. Rumors circulated at the time that Davis and Pitt’s love scene inspired a real-life romance between the two in the early 1990s. Brad’s former roommate Jason Priestly told The Hollywood Reporter that Pitt and Davis unofficially dated for a year after production on the film wrapped, but Davis, who was much more famous at the time, made sure that all their meetups were done in secret.

Everett Collection

Thandie Newton

In 1994, Brad Pitt met Thandie Newton on the set of Interview With the Vampire. He dated the then-22-year-old Newton for a year after they met on set. The pair reportedly had an amicable split and continued to remain friends even after their romantic relationship ended. Pitt has been quiet about the relationship, but did tell Entertainment Weekly that the only good thing that came out of working on the 1994 film was “his love affair with New Orleans.”

© OConnor/AFF-USA.com

Gwyneth Paltrow

One of the most epic Hollywood romances from the ’90s has to be the relationship between Brad Pitt and Gwyneth Paltrow. The pair met while on the set of Se7en quickly became one of Hollywood’s it-couples of the mid-’90s. While accepting his 1996 Golden Globe for Best Supporting Actor, Pitt called Paltrow the love of his life and thanked his “angel” for her support. Pitt proposed to Paltrow in 1996, but they called off their engagement just seven months later. Paltrow later opened up about the relationship in January 2015: “I definitely fell in love with him,” she said. “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.”

(Photo by Lawrence Schwartzwald/Sygma via Getty Images)

Claire Forlani

Following his split from Paltrow, Pitt moved on and was rumored to be dating his Meet Joe Black costar, Claire Forlani. The couple walked hand-in-hand at the red carpet for their movie which had fans buzzing about a potential romance. They made their debut as a couple at the 50th annual Writers’ Guild of America Awards in 1998. Forlani and Pitt have never spoken out or confirmed their relationship, or the reason they eventually called it quits.

(Photo By Getty Images)

Jennifer Aniston

Perhaps the reason Forlani and Pitt never worked out is because in 1998, he was set up by his agent on a blind date that would change everything. Brad Pitt and Jennifer Aniston began dating in 1998 and instantly became one of the most high-profile celebrity couples of the era. The duo continue to date for two more years before Pitt popped the question, and they wed in a lavish ceremony in Malibu the following year. After five years of marriage, unfortunately, the Hollywood golden couple announced that they would be separating.

(Photo by Toni Anne Barson Archive/WireImage)

Angelina Jolie

In 2004, sparks flew between Brad Pitt and Angelina Jolie on the set of Mr. and Mrs. Smith. Following his split from Aniston, Jolie and Pitt became inseparable and fans assumed that he had finally found the love of his life. Following a two-year engagement, the actors finally tied the knot in 2014, and went on to have six children together: Maddox, Zahara, Pax, Shiloh, and twins Knox and Vivienne. Fans were shocked when the pair announced they would be divorcing just two years in 2016, citing irreconcilable differences as the reason for their split.

Photo By: Dee Cercone/Everett Collection

Olivia DiPede

Olivia DiPede

Olivia loves all things beauty, fitness and health. In her free time, she can be found taking yoga classes, visiting Sephora and creating content for her personal lifestyle blog. She loves to travel to new countries, read thriller novels and spend time with her family.

X