Brad Pitt’s Star-Studded Love Life: From Gwyneth Paltrow to Angelina Jolie

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Brad Pitt's Star-Studded Love Life: From Gwyneth Paltrow to Angelina Jolie

Brad Pitt is considered one of Hollywood's most eligible bachelors — and he has the lengthy list of former flames to prove it. The Hollywood superstar may not have caught the public’s eye until starring as a cowboy hitchhiker in the 1991 film Thelma & Louise, but his handsome features and irresistible charm were already a staple in the industry dating pool long before then. In 1984, Pitt was linked to British-American singer Sinitta, whom he dated off and on for two years. The “Love and Affection” singer later revealed during a stint on the U.K.’s I’m a Celebrity...Get Me Out of Here that the young Pitt was “beautiful with the most amazing body" and “very sweet” while they were together. Following a series of brief relationships with costars from his guest appearances on TV shows like Dallas and Head of the Class, the Inglourious Basterds star popped the question to Cutting Class actress Jill Schoelen in 1989. Their engagement lasted only eight months before Schoelen reportedly found a new man while shooting a movie in Hungary. Nearly 10 years later, Pitt was engaged once again — this time to Se7en costar Gwyneth Paltrow. The two were viewed as Hollywood’s next It Couple before calling it quits in 1997. In 2015, Paltrow opened up to Howard Stern about the “devastating” end of her relationship with Pitt. "I was such a kid,” the Politician star said at the time. “I wasn't ready, and he was too good for me." [jwplayer 8uSQitbl-zhNYySv2] After a brief stint with actress Claire Forlani, Pitt was set up on a blind date with Jennifer Aniston in 1998. The two quickly hit it off and were dubbed Hollywood’s latest golden couple. The Morning Show star tied the knot with Pitt in 2000, and her man made a guest appearance on Friends the following year. Although Aniston had revealed hopes of starting a family with the Fight Club star, their union ended before they had the chance. In January 2005, the couple formally announced their separation. “We would like to explain that our separation is not the result of any speculation reported by the tabloid media," the pair said at the time. Their divorce was finalized nine months later. Aniston wasn't the last woman to steal Pitt's heart. After meeting on the set of Mr. and Mrs. Smith in 2004, the actor struck up a romance with his costar Angelina Jolie. Pitt eventually adopted Jolie's kids, Zahara and Maddox, in 2006 before welcoming daughter Shiloh the same year. The couple also share adopted children Pax, Vivienne and Knox. All of their kids accompanied Jolie and Pitt to their dreamy French wedding in 2014. Two years later, the beloved couple split. Scroll down to learn more about Pitt's star-studded love life! [podcast_block]

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Sinitta

The British-American singer and Pitt dated on and off between 1984 and 1986. Following Pitt’s split from Jolie in 2016, the “So Macho” singer insisted that the Hollywood hunk wanted to reignite their old flame.

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Shalane McCall

After appearing on four episodes of Dallas as McCall’s boyfriend, the two were rumored to have taken their romance off-screen between 1987 and 1988. The next year, the Dallas actress tied the knot with Trent Valladares and never looked back.

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Robin Givens

Legend has it that Givens and Pitt were caught in bed together by Givens’ ex-husband Mike Tyson before the couple finalized their divorce in 1989. In June 2019, however, the Head of the Class actress denied the affair during an appearance on Watch What Happens Live With Andy Cohen.

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Jill Schoelen

You never forget your first fiancée. Pitt and his Cutting Class costar were engaged for eight months in 1989, but their flame burned out when the two rendezvoused in Budapest, Hungary. In 2011, the Fight Club star reportedly told The Sun, “She told me that she had fallen in love with the director of the film. I was so shocked I said, 'I'm outta here.'"  

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Christina Applegate

Pitt escorted the Married...With Children star to the 1989 MTV Video Music Awards, but she infamously ditched him for another man during the event. Applegate has never revealed specifically who the mystery man was, she confirmed to Andy Cohen in 2015 that the person was not an actor.

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EG Daily

The PeeWee’s Big Adventure star was rumored to have been the one to console a heartbroken Pitt following his 1989 split from Schoelen.

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Juliette Lewis

The costars began dating after meeting on the set of Too Young to Die in 1990 when then 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.”

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Geena Davis

According to Pitt’s former housemate, Jason Priestly, the legendary Thelma & Louise love scene inspired a real-life romance between Pitt and Davis in the early 1990s.

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Thandiwe Newton

The Interview With the Vampire star had previously admitted to Entertainment Weekly that the only good thing that came out of working on the 1994 film was his “love affair with New Orleans.” However, a love affair with Newton was also rumored to emerge from the movie.

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Gwyneth Paltrow

This iconic mid-'90s couple were head over heels for each other after meeting on the set of Se7en. While accepting his Golden Globe for Best Supporting Actor in 1996, Pitt thanked his “angel” and called Paltrow the love of his life, only to call it quits with the Emmy winner a year later.

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Claire Forlani

Following his split from Paltrow, Pitt was rumored to move on with his Meet Joe Black costar. The pair made their red carpet debut at the 50th annual Writers’ Guild of America Awards in 1998.

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Jennifer Aniston

The one that got away. Aniston and Pitt were set up on a blind date by their agents in 1998, and the two instantly became one of the most high-profile celebrity couples of the era. However, Hollywood’s golden couple formally announced their separation in January 2005 after five years of marriage. They have since become friends again.

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Angelina Jolie

Sparks flew on the set of Mr. and Mrs. Smith in 2004, and the rest is history. Following a two-year engagement, the actors finally tied the knot in 2014. Jolie filed for divorce two years later, citing irreconcilable differences.

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Alia Shawkat

In 2019, the Once Upon a Time in Hollywood actor was rumored to be dating Arrested Development alum Alia Shawkat after being spotted together at an art exhibition in Los Angeles. However, a source told Us at the time that the two are “just friends.”

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Nicole Poturalski

Us confirmed in August 2020 that Pitt was dating the German model after they were spotted at Le Bourget airport outside of Paris. Pitt and Poturalski kept a low-profile as they made their way to the actor’s chateau in the South of France.

Just two months later, however, Us confirmed that Pitt and Poturalski called it quits. “Brad and Nicole have been over for a while now,” an insider revealed at the time. “They had a short-lived relationship that was never too serious.”

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Emily Ratajkowski

Us confirmed in September 2022 that Pitt had been on a few dates with the Gone Girl actress amid her divorce from Sebastian Bear McClard, with whom she shares son Sylvester.

“Brad and Emily have been on a few dates and have been enjoying each other’s company,” a source told Us one month later, noting the Bullet Train star is “playing the field” in terms of dating. “He’s really enjoying the process of putting himself out there and going with the flow as a single guy. [He’s] taking his time before committing to anything serious.”

After Ratajkowski’s few dates with Pitt, the My Body author has since been linked to Pete Davidson.

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Ines de Ramon

The Burn After Reading actor was spotted out and about with the jewelry designer several times in November and December 2022 before a source confirmed to Us that the pair are romantically involved.

“Brad and Ines are officially dating now. They really enjoy each other’s company and are having a great time in the early stages of an early relationship, but are still getting to know each other,” the insider said in December 2022.