As one of the most handsome and famous men on the planet, Brad Pitt has quite the A-list dating history.
The Oscar winner counts several Hollywood superstars as his exes, including former wives Angelina Jolie and Jennifer Aniston, former fiancée Gwyneth Paltrow and ex-girlfriends including Juliette Lewis, Christina Applegate and more.
Pitt himself has insisted that most rumors about his personal life as a whole are false, especially when it comes to his relationships. He told The New York Times Magazine in December 2019, “I stopped reading all press about 2004. Not just reviews. I mean any magazine in the doctor’s office,” he said. “Because some of it would bounce around like a rat in the skull. It would stay there, and it would inform some of my decisions and choices in work, in life, and I didn’t find any of it helpful.”
“I don’t go out of my way to avoid it; I just don’t seek it out,” he explained. “I don’t know how many women they’ve said I’ve been dating the last two or three years, and none of it’s true.”
These days, following his difficult divorce from Jolie, with whom he shares six children (Maddox, Pax, Zahara, Shiloh and twins Vivienne and Knox), Pitt has been keeping his dating life more low-key.
“He has a large group of artsy friends in L.A. that he hangs out with,” a source told PEOPLE of the Bullet Train star. “He’s dating, but is not in a serious relationship.”
Ahead, a complete look at Brad Pitt’s dating history, from his reported fling with singer Sinitta in the ’80s to his most recent connection with model Emily Ratajkowski.
Pitt and singer Sinitta reportedly dated from 1986 to 1988. The British pop star told her castmates on I’m a Celebrity … Get Me Out Of Here! in 2011 (via Marie Claire UK) that Pitt was “beautiful with the most amazing body,” adding, “I saw him for two years. He was fun, he was young and very sweet. Some ardent fan gave me a slap when I came out of a supermarket over that relationship.”
She added, “It was before he made Thelma & Louise, but even I saw that movie and thought, “Oh my God, what have I done?’ “
Pitt dated actress Jill Schoelen in the late 1980s after they met on the set of the horror movie Cutting Class.
In Pitt’s E! True Hollywood Story, voice actress Elizabeth “E.G.” Daily revealed that she had a rebound romance with the star after he and Schoelen split. Daily described Pitt as “deep-souled” and “super cute” and said they connected in various ways.
“I think he was really intense about his work,” Daily said. “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.”
After Daily and Pitt called it quits on their brief romance, they remained friends.
Pitt and Robin Givens were costars on Head of the Class and grew close when she and then-estranged husband Mike Tyson separated. Tyson alleged in his memoir Undisputed Truth that he pulled into his and Givens’ driveway and saw her in a car with Pitt; he also claimed to have caught the pair in bed while Tyson and Givens were still together.
In a 2019 interview on Watch What Happens Live with Andy Cohen, Givens denied an affair with Pitt.
“Pulling up in the driveway, that part is true,” Givens said at the time. “I didn’t read the book, but I was told he says he caught us in bed, which never happened. Never, ever, ever happened.”
As for why she and Pitt were in the car together, Givens said, “We were coming from like a screening or something.”
Christina Applegate once recalled that Pitt and his former roommate, 90210 star Jason Priestley, would come to barbecues on the set of Married … With Children when she was a teen. She and Pitt were photographed getting cozy several times (including here at an Amnesty International event in 1988), and Pitt was her date to the 1989 MTV Movie Awards — until she ditched him for another guy.
During a “Plead the Fifth” segment on Watch What Happens Live With Andy Cohen in 2015, Applegate wouldn’t reveal the identity of the mystery man, but did note that she and Pitt didn’t date after the incident — nor did she date the man for whom she left him.
Pitt and Juliette Lewis dated from late 1989 to 1993 and the pair costarred in Kalifornia and Too Young to Die.
Two years after their breakup, Pitt told Vanity Fair of Lewis, “I still love the woman. There’s some real genius there. I had a great time with her … It was one of the greatest relationships I’ve ever been in.” He added, “The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?”
Though they remain friendly and each look back on the time fondly, Lewis isn’t too keen on being asked about her megastar ex.
In 2014, Lewis told PEOPLE that most press about her when she was younger was “usually about Brad Pitt or drug addiction, which hasn’t been me since I was 22. I’m 40. I quit all my bulls— at 22. There is growth. Get out of the past.”
Pitt brought model Jitka Pohlodek as his date to the premiere of Legends of the Fall in November 1994, but neither has spoken publicly about their brief romance. However, Pohlodek did later share one glimpse into her connection with the actor, telling PEOPLE in 2000, “The man glows.”
Pitt met Gwyneth Paltrow when she played his wife in the 1995 thriller Se7en. Pitt called Paltrow his “angel” and the “love of [his] life” in his 1996 Golden Globes acceptance speech for Best Supporting Actor in 12 Monkeys, and the pair got engaged that December. However, they split in June 1997 before ever making it down the aisle, and the Goop founder later recalled that her father, Bruce Paltrow, was particularly devastated because he adored Pitt.
Gwyneth and Pitt remained close, however, with Pitt telling her in a June 2022 conversation, “It’s lovely to have you as a friend now.”
Pitt met Jennifer Aniston in 1998. He proposed to the Friends star in 1999, and the couple married in Malibu on July 29, 2000. The wedding featured some 200 guests, 50,000 flowers, four bands, a gospel choir and fireworks. “Jennifer looked beautiful,” her father, Days of Our Lives actor John Aniston told PEOPLE after escorting his daughter down the aisle. “It was a spectacular wedding.”
In January 2005, Pitt and Aniston shocked the world when they announced their split.
“We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media,” the pair said in a joint statement to PEOPLE. “This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.”
Aniston filed for divorce from Pitt in March 2005, and by October, their divorce was finalized. In recent years, Pitt and Aniston have become platonic friends. In 2017, following Pitt’s split from Angelina Jolie, it was reported that he and Aniston texted occasionally, and the actor attended her 50th birthday party in 2019. Though Pitt and Aniston had a memorable run-in at the 2020 Screen Actors Guild Awards and a clearly enjoyable table-read of Fast Times at Ridgemont High, insiders have said they’re not pursuing a romantic reconciliation.
“They broke up, and they did it because they had serious issues,” a source told PEOPLE in 2018. “They’re not stupid. They remember why it didn’t work.”
In 2021, Aniston made it clear in an interview with Howard Stern that she and Pitt are “buddies” and “friends.”
Jolie and Pitt met while filming Mr. & Mrs. Smith in 2003, while he and Aniston were still married. Jolie recalled to Vogue in 2007 that she and Pitt worked well together, though they didn’t become romantic right away.
“Because of the film, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened,” she said. “I think a few months in I realized, ‘God, I can’t wait to get to work.’ … Anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair.”
About Pitt’s marriage to Aniston, Jolie noted, “I didn’t know much about exactly where Brad was in his personal life. But it was clear he was with his best friend, someone he loves and respects.” She added, “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.”
Pitt and Aniston separated in January 2005. That summer, Jolie, already mom to son Maddox, adopted daughter Zahara Marley; in January 2006, Maddox and Zahara’s last names were legally changed to Jolie-Pitt. A friend of “Brangelina” told PEOPLE at the time, “It’s the idea that you love one another and you want to create a family together. What’s beautiful is you can do it by birth (or) by adoption.” That same month, Pitt and Jolie confirmed that Jolie was pregnant.
In May 2006, Pitt and Jolie welcomed daughter Shiloh Nouvel. That December, they made their red carpet debut as a couple at the New York City premiere of Jolie’s film The Good Shepherd. The following year, they adopted their son Pax Thien from Vietnam.
On Feb. 23, 2008, Jolie debuted a baby bump at the Independent Spirit Awards, and it was later revealed she was pregnant with twins. The couple welcomed son Knox Léon and daughter Vivienne Marcheline on July 12, 2008. Jolie told PEOPLE of their expanded family at the time, “It is chaos, but we are managing it and having a wonderful time.”
By 2012, Pitt revealed that his and Jolie’s children urged them to get married, and a rep for the pair confirmed their engagement that April (with a ring estimated to be worth a cool $1 million). Pitt and Jolie tied the knot on Aug. 23, 2014, at the chapel in their Château Miraval estate, with Jolie wearing a gown that her children decorated with their own art. The children even helped the couple write their own vows.
“It was important to us that the day was relaxed and full of laughter,” the couple told PEOPLE at the time. “It was such a special day to share with our children and a very happy time for our family.”
During their 2014 honeymoon, Jolie and Pitt worked together on By the Sea, released in fall 2015.
On Sept. 20, 2016, just over two years after their second wedding anniversary, Jolie filed for divorce from Pitt. A rep for Jolie said in a statement, “Angelina Jolie-Pitt has filed for dissolution of the marriage. This decision was made for the health of the family. She will not be commenting at this time, and asks that the family be given their privacy during this difficult time.”
Pitt said in a separate statement, “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.”
It was later revealed that Jolie’s filing came shortly after an alleged heated altercation on a private plane became physical. Pitt denied striking any of the couple’s children, and the Los Angeles Department of Child and Protective Services found no evidence of abuse. The FBI also closed an investigation into the incident without filing charges against the Fight Club star.
By April 2019, the estranged pair were declared legally single, but contentious negotiations over custody and division of assets — most famously their winery — remain ongoing.
Following his split from Jolie, Pitt spent time with MIT professor and architect Neri Oxman in April 2018.
“It took him a long time to date, but he is now,” a source told PEOPLE, noting how George and Amal Clooney’s relationship inspired Pitt. “He likes women who challenge him in every way, especially in the intellect department. Brad has seen how happy and different Amal has made his friend. It has given him something to think about.” However, that October, Oxman denied ever dating the actor, but praised him as “the last of the Mohicans in post-Netflix Hollywood … He brings together the timely and the timeless, which is what cinema is all about.”
Pitt dated model Nicole Poturalski in the summer of 2020, though the pair knew each other for at least a year before romance rumors came to light. A witness told PEOPLE that Pitt and Poturalski were spotted together at a 2019 Berlin Film Festival party for Once Upon a Time … In Hollywood, noting, “They were very flirty.”
In August 2020, Pitt and Poturalski were spotted at Château Miraval in France, where a source said they were “enjoying each other’s company while traveling.” An industry insider also told PEOPLE that Poturalski was a good match for Pitt, saying, “I like her a lot. She has spunk. She’s smart. If she’s dating Brad, good for her. Good for him.”
However, just two months later, a source revealed to PEOPLE that Pitt and Poturalski were never serious, explaining, “Brad hasn’t seen Nicole since August. It was never a relationship. They saw each other a few times and that’s it. You can’t call it a split, because they were never together in the first place. It was a casual fling and that’s it.” Still, another source told PEOPLE in January 2022 that Pitt “still keeps in touch” with the model.
Pitt was linked to model Emily Ratajkowski in late September 2022 following her split from estranged husband Sebastian Bear-McClard. A source told PEOPLE that the pair are “spending a lot of time together,” though “friends aren’t sure if it’s serious,” and the two don’t “appear to be ‘dating’ formally.”