America’s favorite heartthrob, Brad Pitt, has had an impressive A-list dating history. With famous ex-wives and girlfriends, this actor is used to being in the spotlight. He vehemently denies that rumors around his personal life (and his relationship) are false, even going so far as to say that he stopped reading all press and tabloids in 2004. Here’s Brad Pitt’s full romantic history over the years, from the 1980s up until the present day.
Sinitta
Reportedly, Pitt dated this singer in the 80s, and in 2011, she told castmates on the show “I’m a Celebrity … Get Me Out Of Here!” that he was “beautiful with the most amazing body,” confirming they dated for around two years, and she often dealt with his crazy and jealous fans, including one who slapped her when she came out of a supermarket.
Jill Schoelen
Before he skyrocketed to fame, Pitt dated the actress Jill Schoelen in the late 80s. They met on the set of the horror film “Cutting Class.” These young lovers were reportedly briefly engaged but broke up when the actress confessed that she fell in love with a film director.
E.G. Daily
Voice actor Elizabeth “E.G.” Daily called Brad Pitt a rebound relationship in his E! True Hollywood Story. Still, the connection was more than a hookup, with E.G. calling him “super cute” and “deep-souled” but admitting that he was intense about his work as an actor, citing a “really strong, visceral drive.” The two remained friends after they split.
Robin Givens
After Givens split from her husband, Mike Tyson, she costarred with Pitt on “Head of the Class,” and their friendship blossomed into something more. According to Tyson, the two got together while the couple was still very much together, and he claimed to have caught them in bed! Givens said that while her ex did see her in their driveway together after attending a screening with Pitt, the more scandalous part of the rumor wasn’t true.
Christina Applegate
These two icons met at barbecues on the set of “Married … With Children” when Applegate was just a teen, and there are several photos of them getting cozy at different events, including the 1989 MTV Movie Awards, where he was her date. Like Schoelen, she left him for another man. She won’t reveal who it was, but she did say on Andy Cohen’s “Watch What Happens Live” that she never dated Pitt again after the incident.
Juliette Lewis
These actors dated for about four years starting in 1980 and also costarred in the movies “Too Young to Die” and “Kalifornia.” Years after breaking up, Pitt told Vanity Fair that he still loved her, calling her a genius and saying it was one of the “greatest relationships” he’s ever been in. The two are still friendly, but Lewis doesn’t like being asked about her relationship with the megastar, saying that she’s often asked about Pitt or her former drug addiction.
Jitka Pohlodek
Brunette beauty Jitka Pohlodek was a model that Pitt dated in the 1990s and whom he brought to the premiere of “Legends of the Fall” in 1994. They’ve both been hush-hush about their brief relationship, but Pohlodek told PEOPLE in 2000 that “the man glows,” even though he had told Vanity Fair then that he still loved Juliette Lewis.
Gwyneth Paltrow
Paltrow and Pitt met on the set of the 1995 thriller Se7en, and the actor called her the love of his life in his 1996 Golden Globes acceptance speech. They got engaged in December 1995 but split up in 1997 before getting married. According to her episode on the podcast Call Her Daddy, Paltrow wasn’t ready for marriage, but they remained friends. On the podcast, she called it “major, major love at first sight.”
Jennifer Aniston
Pitt met Aniston in 1998, proposed in 1999, and married a year later in 2000. The wedding was the event of the year with four bands, over 200 guests, a gospel choir, 50,000 flowers, and fireworks. Sadly, just five years later, they announced their breakup and filed for divorce in March 2005. After he broke up with Angelina Jolie, it was reported that the two texted once in a while and that he came to her birthday party in 2019, but insiders confirmed they’re not looking to get back together.
Angelina Jolie
These two met on the set of Mr. & Mrs. Smith in 2003 but didn’t start dating right away, especially as Pitt was still with Aniston. However, the two couldn’t deny their romance by the end of the film. Pitt and Aniston split in 2005, and by 2006, Zahara and Maddox changed their last names to Jolie-Pitt. The same month, Jolie announced she was pregnant with Shiloh. They then adopted Pax Thien, and in 2008, Angie was pregnant again. The couple made it official by marrying in 2014 after being urged by their kids, but in 2016, after just two years of marriage, they went through an ugly divorce following a heated fight on a private plane that evidently turned physical. Negotiations spanned five years, and their legal battle over their winery continues to this day.
Ines de Ramon
After Pitt and Jolie broke up, the actor was rumored to be dating several women, including Alia Shawkat, Sat Hari Khalsa, and Neri Oxman. The only one that stuck was his relationship with Ines de Ramon, a jewelry company executive he was first connected to in November 2022 after being spotted at a Bono concert in LA together. Public knowledge revealed that she moved into his home in 2024, the same year they made their red carpet debut together.
