From Gwyneth Paltrow and Jennifer Aniston to Angelina Jolie: A look at Brad Pitt’s star-studded dating history
CARMEL, CALIFORNIA: Brad Pitt is considered to be Hollywood’s most eligible bachelor and the long list of his former love affairs is testimony to it. The ‘bullet train’ actor who became the hot topic of the town after his ex-wife Angelina Jolie accused him of physically abusing her and their children, has quite a long A-list dating history.
There is no denying the fact that the ‘Money Ball’ actor has made tons of headlines for his personal life. Talking about his former flames, Brad has dated a ton of super talented and famous women and has also been married twice and engaged three times. From his fling with British singer Sinitta to his reported affair with model Emily Ratajkowski, here we bring you a look at Brad Pitt's star-studded dating history.
Brad and singer Sinitta reportedly dated on and off between 1984 and 1986. Because the internet not being quite a thing back then, the duo managed to keep their relationship under the wrap. However, their romance came out when 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."
Pitt soon moved on and met his first fiancée. Brad dated actress Jill Schoelen in the late 1980s whom he met on the set of his horror classic 'Cutting Class'. Without wasting any time, Pitt popped the question and the duo got engaged in 1989. But tragically the engagement lasted for just three months as Schoelen reportedly dumped Pitt for a director of her another movie.
Elizabeth "EG" Daily
The star then had a rebound romance with voice actress Elizabeth "EG" Daily. "I think he was really intense about his work," Daily told E! True Hollywood Story "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." However, the couple soon called it off and decided to remain friends.
Robin Givens met Pitt on the set of their movie 'Head of the Class' while she was trying to cope with her separation from husband Mike Tyson. Tyson in his memoir ‘Undisputed Truth’ revealed that he caught his wife with Brad in bed while Tyson and Givens were still together. But in an interview in 2019, Givens denied an affair with Pitt. "Pulling up in the driveway, that part is true," Givens told Andy Cohen on Watch What Happens Life "I didn't read the book, but I was told he says he caught us in bed, which never happened. Never, ever, ever happened."
Pitt and Applegate briefly dated in 1989 and the 'Once Upon A Time In Hollywood' actor even escorted her to the MTV Movie Awards that year. But bad luck for Brad, Applegate ditched him for another guy during the event. During a "Plead the Fifth" segment on 'Watch What Happens Live With Andy Cohen' in 2015, Applegate revealed that after that incident, she and Pitt never dated nor she dated that mysterious guy.
Pitt and Juliette Lewis dated each other from late 1989 to 1993 after meeting on the set of their first movie together 'Too Young to Die' in 1990. The pair then co-starred in 'Kalifornia'. At the time of their affair, 27-year-old Pitt was a decade older than Lewis. While filming 'Kalifornia' together in 1993, Lewis told the Los Angeles Times, “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.”
Geena Davis and Brad were declared couple after their steamy sex scene in 1991's 'Thelma & Louise'. The couple secretly dated each other for more than a year and called it off after the wrap-up of their movie. Brad’s former roommate Jason Priestley told Hollywood Reporter that the much-more-famous Davis made sure all of their meetups were done in secret.
‘The Lost City’ actor kept his love life low-key until he met Gwyneth Paltrow, who played his wife in the 1995 thriller 'Se7en'. It didn’t take long for Pitt to fall head over heels in love with his co-star. Flexing his love, Pitt called Paltrow his "angel" and the "love of [his] life" in his 1996 Golden Globes acceptance speech. The truly and madly in love pair got engaged in December 1996. However, the pair didn’t manage to make it to the aisle as they broke up in June 1997. The 'Goop' founder later recalled that her father, Bruce Paltrow, was particularly devastated because he adored Pitt.
Aniston and Pitt met each other when they were riding success for their on-screen performances. The couple met each other in 1998 after their respective agents set them up on a blind date. The Hollywood golden couple continued to date for two more years before Pitt popped the question, and they had a lavish, million-dollar wedding in Malibu. The happy couple left the world heartbroken when they announced their divorce in 2005. The couple reportedly called it off because of Aniston's will to not have kids. "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."
The 'Friends' star filed for divorce from Pitt in March 2005 and by the end of October 2005, their divorce was finalized.
Angelina Jolie met Brad on the set of their movie 'Mr and Mrs Smith', while he was still married to Aniston. The couple’s work on-screen left the audience astonished and made the audience blame Jolie for Pitt’s divorce from Aniston. After Pitt’s divorce from Aniston, Jolie, already a mother of son Maddox, adopted her daughter Zahara Marley; in January 2006. Then their followers got to know that the legal name of Jolie’s kids Maddox and Zahara has been changed to Jolie-Pitt. That year, the couple made their debut as a couple at the New York City premiere of Jolie's film 'The Good Shepherd' and decided to welcome their daughter Shiloh Nouvel. 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. In 2012, Pitt revealed that their children are forcing them to get married to their manager confirming their engagement in April that year. 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.
But following a storm in their love life, Jolie filed for divorce from Pitt in September 2016. 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."
Trying to move on from Angelina Jolie, a rebound romance brewed up between Pitt and MIT professor and architect Neri Oxman in April 2018. Many sources close to Brad confirmed their relationship at that time. But that October, Oxman denied ever dating the actor, but praised him as "the last of the Mohicans in post-Netflix Hollywood.”
In August 2020, Us Weekly confirmed that Pitt was dating the then-27-year-old German model after they were spotted arriving at the Le Bourget airport outside of Paris. From there, they appear headed to Château Miraval, Pitt's getaway home in the South of France. The couple split two months later. A source confirmed the news to Us Weekly and said the romance was a "short-lived relationship that was never too serious."
Lately, Brad claimed to be staying away from dating and focusing on his career. But his link with model Emily Ratajkowski had something else to say. The actor was linked with a model in late September 2022 following her split from estranged husband Sebastian Bear-McClard. Later that month, multiple sources confirmed their casual relationship. 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."