Brad Pitt Dating History: From Angelina Jolie To Ines de Ramon

Let's take a look back at Brad Pitt's dating history, from 1988 to now.

Published on Feb 29, 2024  |  12:58 PM IST |  87K
Brad Pitt (IMDb)
Brad Pitt (IMDb)

Brad Pitt has a dating history that is filled with A-list actresses. From iconic relationships with Angelina Jolie and Jennifer Aniston to shorter ones with stars like Gwyneth Paltrow and Juliette Lewis. Here's a list of all of Brad Pitt's romances.

Sinitta Malone (1986-1988)

One of Pitt's earliest romances was with British pop star Sinitta Malone, dating from 1986 to 1988. Malone, known for her time on "I'm a Celebrity … Get Me Out Of Here!" shared glimpses of their relationship, describing Pitt as "beautiful" and "fun." Their two-year happened before Pitt's breakout role in "Thelma & Louise."

Jill Schoelen (1989)

In the late 1980s, Pitt was  briefly involved with actress Jill Schoelen, whom he met on the set of the horror film "Cutting Class." 

E.G. Daily (1989-1990)

Following the separation from Schoelen, voice actress Elizabeth "E.G." Daily entered Pitt's life as a rebound romance. Daily described Pitt as "deep-souled" and "super cute," highlighting the actor's intense dedication to his craft during their brief connection.

Robin Givens (1988-1989)

Pitt's involvement with Robin Givens, his co-star on "Head of the Class," stirred controversy amid Givens' tumultuous marriage to Mike Tyson. Denying allegations of an affair, Givens clarified the nature of their relationship, shedding light on a period of tabloid speculation.

Christina Applegate (1989)

Christina Applegate once shared a memory about Brad Pitt and his former roommate, Jason Priestley, who used to attend barbecues on the set of Married... with Children when she was a teenager. There were several instances where Applegate and Pitt were photographed getting cozy, including at an Amnesty International event in 1988. In 1989, Pitt was her date for the MTV Movie Awards, but Applegate ditched him for another man - whose identity she chose not to reveal during a "Plead the Fifth" segment on Watch What Happens Live With Andy Cohen in 2015. 


Juliette Lewis (1989-1993)

Pitt and Juliette Lewis were in a relationship from late 1989 to 1993. They also worked in two movies together, Kalifornia and Too Young to Die. Two years after their break-up, Pitt spoke to Vanity Fair about Lewis, saying that he still loved her. He described their relationship as one of the greatest he had ever been in, but he also acknowledged that the idea that love conquers all is not entirely true. While they remain on good terms and have fond memories of their time together, Lewis doesn't like it when people ask her about her famous ex. 

Jitka Pohlodek (1994) 

Model Jitka Pohlodek accompanied Pitt to the premiere of "Legends of the Fall" in 1994, offering a glimpse into a romance that remained mostly private. Pohlodek's admiration for Pitt, describing him as a man who "glows." 

Gwyneth Paltrow (1995-1997)

Brad Pitt and Gwyneth Paltrow (via Getty Images)

Brad Pitt and Gwyneth Paltrow first met on the set of the 1995 thriller Se7en, where Paltrow played Pitt's wife. In his 1996 Golden Globes acceptance speech for Best Supporting Actor in 12 Monkeys, Pitt referred to Paltrow as his "angel" and "the love of [his] life." They got engaged in December of that year, but they split in June 1997 before they could get married. Paltrow later revealed that her father, Bruce Paltrow, was particularly upset about the breakup because he loved Pitt.

Despite the breakup, Pitt and Paltrow remained friends. In a conversation in June 2022, Pitt told Paltrow that he was happy to have her as a friend. During an appearance on a May 2023 episode of the Call Her Daddy podcast, Paltrow reminisced about their relationship, describing it as "major, major love at first sight." She also recalled how Pitt proposed to her on the balcony of a rented house in Argentina. Although she couldn't remember exactly what he said, she was thrilled and surprised by the proposal.

Jennifer Aniston (1998-2005)

Brad Pitt and Jennifer Aniston (via Getty Images)

Brad Pitt and Jennifer Aniston met in 1998 and got married in Malibu on July 29, 2000, in a grand wedding ceremony attended by some 200 guests. In January 2005, the couple announced their split after seven years together, and their divorce was finalized by October of the same year.


However, in recent years, Pitt and Aniston have rekindled their friendship, and they are now friends who occasionally text and attend each other's events. Although there have been rumors of a romantic reconciliation, insiders say that they're not pursuing it. In an interview with Howard Stern in 2021, Aniston confirmed that she and Pitt are just "buddies" and "friends."

Angelina Jolie (2003-2016)

Brad Pitt and Angelina Jolie (via Getty Images)

Jolie and Pitt first met in 2003 while filming Mr. & Mrs. Smith. Pitt was still married to Aniston at the time. Jolie said in an interview with Vogue in 2007 that they became friends and partners after working together on the film. They didn't realize they had romantic feelings for each other until the end of the shoot. Jolie also said that she didn't know much about Pitt's personal life at the time, but it was clear that he was with someone he loved and respected.

Pitt and Aniston separated in January 2005. That summer, Jolie adopted her daughter Zahara Marley, and in January 2006, both Zahara and Maddox (Jolie's son before she met Pitt) legally changed their last names to Jolie-Pitt. A friend of the couple told PEOPLE at the time that they wanted to create a family together, whether through birth or adoption. In May 2006, Pitt and Jolie welcomed their first biological child, a daughter named Shiloh Nouvel. The couple adopted their son Pax Thien from Vietnam the following year.

In February 2008, Jolie announced her pregnancy with twins, Knox Léon and Vivienne Marcheline, who were born in July of that year. 

In 2012, their children urged them to get married, and the couple confirmed their engagement that April. They tied the knot in August 2014 at their estate in France, with their children helping to write their vows and even decorate Jolie's wedding dress.

During their 2014 honeymoon, Jolie and Pitt worked together on the film By the Sea, which was released in 2015. However, just over two years after their wedding, Jolie filed for divorce from Pitt in September 2016, citing the health of the family as the reason. Pitt released a statement saying he was saddened by the news but that the well-being of their children was the priority.

Neri Oxman (2018)

Post-divorce, Pitt's was linked with MIT professor Neri Oxman. A source told PEOPLE, "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."


Nicole Poturalski (2019-2020)

In the summer of 2020, Pitt's rumored romance with model Nicole Poturalski gained attention, neithewr ever confirmed anything and it eventually faded.

Emily Ratajkowski (2022)

Model Emily Ratajkowski was liknked Pitt's orbit in late 2022, following her separation from Sebastian Bear-McClard, nothing was ever confirmed.

Ines de Ramon (2022-)

Pitt and de Ramon were first seen together at a Bono concert in Los Angeles on November 13, 2022. This was approximately two months after the news broke out that de Ramon and her husband Paul Wesley had quietly separated in early 2022.


In December 2022, Pitt took de Ramon to the Los Angeles premiere of his film "Babylon." The couple was reportedly seen socializing with their arms around each other at the after-party. 

A few days later, de Ramon and Pitt celebrated his 59th birthday together. The couple, dressed casually, were photographed arriving at Pace, an Italian restaurant in Hollywood.

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