Brad Pitt’s dating history is as star-studded as they come.
Not only has the actor been married to two A-listers — Jennifer Aniston and Angelina Jolie — but he engaged in many high-profile relationships and flings over the years before his current romance with Ines de Ramon.
Pitt’s love life has been just as busy on-screen, with him filming his first sex scene in “Dallas” in the 1980s.
“I had to roll around in the hay in a barn,” he recalled in a June 2023 W Magazine interview. “I don’t think I had a line. I was just rolling and frolicking.”
The Oscar winner went on to declare his famed love scene in 1991’s “Thelma & Louise” to be his “entry into the big leagues.”
Meet all of Pitt’s off-screen flames below.
Sinitta
Sinitta claimed in a 2011 episode of “I’m a Celebrity … Get Me Out of Here” that she dated Pitt from 1984 to 1986.
“He was fun. He was young and very sweet,” the pop star said before gushing over the “beautiful” producer’s “amazing body.”
When Pitt and Jolie called it quits five years later, Sinitta alleged he had “been calling” until she told him to “move on.”
Robin Givens
Between Robin Givens’ 1988 separation and 1989 divorce from Mike Tyson, the “Head of the Class” star was linked to Pitt, who appeared in an episode of the ABC sitcom.
The professional boxer wrote in “Undisputed Truth” that he found duo in a car together, which Givens confirmed was “true” on “Watch What Happens Live with Andy Cohen” in 2019.
“We were coming home from, like, a screening or something,” she recalled.
As for Tyson’s claim that he caught the pair in bed before their breakup, Givens insisted that “never, ever happened.”
Jill Schoelen
Pitt met Jill Schoelen on the set of “Cutting Glass,” and the duo were engaged for months before breaking it off in 1989.
“She told me that she had fallen in love with the director of the film,” the “Interview with the Vampire” star reportedly told the Sun at the time. “I was so shocked. I said, ‘I’m outta here.'”
When Schoelen spoke to Radar online in 2013, she called her ex a “deep and soulful” man who wrote her “the most beautiful poems” during their “beautiful” time together.
Elizabeth “E.G.” Daily
Similarly, Elizabeth “E.G.” Daily” referred to Pitt as “deep-souled” while divulging alleged details of their short-lived romance on “E!’s True Hollywood Story” in 2021.
“I think he was really intense about his work,” the actress said at the time. “When you saw him, it was more like seething in him underneath.
“What I could feel from him was a really strong, visceral drive toward something really big.”
Christina Applegate
While Christina Applegate spent time with Pitt — and his then-roommate Jason Priestley — at “Married… with Children” set barbecues, she “ditched” him on their one date.
The duo were at the 1989 MTV Movie Awards when the actress left Pitt for another guy.
Applegate clarified on “Watch What Happens Live” in 2015 that the mystery man was “known to the public” but not an actor.
Juliette Lewis
After meeting on the “Too Young to Die?” set when he was 27 and she was 17, Pitt and Juliette Lewis dated from 1989 to 1993.
“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,” the “Yellowjackets” star gushed to the Los Angeles Times during their romance.
Since their split, Pitt has looked back on the relationship as one of his “greatest,” telling Vanity Fair in 2011 that he “still love[s] the woman” and “had a great time with her.”
Gwyneth Paltrow
Pitt met Gwyneth Paltrow on the “Se7en” set in 1995 and got down on one knee the following year, only for the former couple to call off their engagement in 1997.
The Goop creator detailed the “fantastic” proposal in a 2023 “Call Her Daddy” episode, recalling, “One night we were on the balcony of this house we were renting in this little town in Argentina. I wish I remember exactly what he said, but … I was thrilled.”
The exes, who experienced “major love at first sight,” remain “friends,” as Pitt proved in a Goop interview the previous year.
Jennifer Aniston
In 1998, Pitt went on a blind date with Jennifer Aniston after being set up by their agents. He proposed to the “Friends” star in 1999, with the duo walking down the aisle in Malibu, Calif., the following year.
They announced their separation with a joint statement in January 2005, writing, “This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another.”
Aniston filed for divorce two months later, which was finalized by October 2005.
The “Morning Show” star told Howard Stern in 2021 that she and her ex-husband are “buddies” and “friends” with “no oddness” between them following their respective splits from Justin Theroux and Jolie.
The duo have proved this amicability over the years, from their “Fast Times at Ridgemont High” table read in 2020 to Pitt attending Aniston’s birthday and holiday parties.
At the 2020 Screen Actors Guild Awards, the exes’ backstage hug went viral.
Angelina Jolie
Pitt was still married to Aniston when he met Jolie on the “Mr. & Mr. Smith” set in 2003.
“I didn’t know much about exactly where Brad was in his personal life,” Jolie told Vogue in 2007. “But it was clear he was with his best friend, someone he loves and respects.
“It took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we’d earlier allowed ourselves to believe. And both knowing that the reality of that was a big thing, something that was going to take a lot of serious consideration.”
The co-stars’ romance took a quick turn, with Pitt adopting Jolie’s son Maddox and daughter Zahara before welcoming daughter Shiloh. The pair went on to adopt son Pax and add twins Vivienne and Knox to their big brood.
Despite getting engaged in 2012 and married in 2014 at their their Château Miraval estate chapel, they ended their relationship in 2016 “for the health of the family.”
At the time, Pitt said, “I am very saddened by this, but what matters most now is the well-being of our kids. I kindly ask the press to give them the space they deserve during this challenging time.”
The split came on the heels of an alleged altercation on a private jet, with Pitt later denying striking their children and the FBI closing its investigation into the incident.
The “Fury” star and Jolie have since engaged in a tumultuous custody and divorce battle, which remains ongoing.
In 2019, however, they were declared legally single.
Nicole Poturalski
Pvnew confirmed in August 2020 that Pitt was dating model Nicole Poturalski after they were spotted traveling in France together, but the duo were “totally over” by that October.
“It was never all that serious as it was cracked up to be,” an insider told us at the time.
In fact, the source said the breakup had happened “awhile back.”
Ines de Ramon
After rumored romantic connections with Emily Ratjkowski and more stars, Pitt moved on with Ines de Ramon.
The fitness trainer, who was previously married to “Vampire Diaries” star Paul Wesley, was first linked to Pitt in 2022. People gave an update on their their status the following year.
“This is Brad’s first proper relationship since the divorce,” a source told the magazine of the “very happy” Emmy winner in 2023. “He introduces [de Ramon] as his girlfriend.”
