Brad Pitt may be one of Hollywood's most legendary stars (with a capital "S"), but he's also had one of Hollywood's most legendary love lifes.
The 60-year-old Academy Award-winning actor is making waves with each update in his personal life, from his legal battle with his ex to his burgeoning new romance.
Recap all of Brad Pitt's most famous (and most significant) love stories over the course of his decades in the spotlight below…
Sinitta
© Getty ImagesBritish-American singer Sinitta reportedly dated the actor from 1986-88, saying on I'm a Celebrity…Get Me Out of Here!: "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."
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She described him as being "beautiful with the most amazing body" and continued: "It was before he made Thelma & Louise, but even I saw that movie and thought, "Oh my God, what have I done?'"
Jill Schoelen
© Getty ImagesBrad and actress Jill Schoelen met on the set of their 1989 movie Cutting Class and dated him during the late 1980s, although some reports state that they were even briefly engaged before calling it quits.
He told The Sun at the time that she had "fallen in love" with her director on the film The Phantom of the Opera. "I was so shocked I said, 'I'm outta here'."
E.G. Daily
© Getty ImagesVoice actress E.G. Daily appeared on E!'s True Hollywood Story to reveal that she had dated the Troy actor briefly following his split from Jill.
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Calling him "deep-souled," she added: "I think he was really intense about his work. 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."
Robin Givens
© Getty ImagesActress Robin Givens and Brad were linked between 1988-89 after the actor appeared in an episode of her show Head of the Class, when she was in the process of divorcing boxer Mike Tyson.
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Mike claimed in his memoir Undisputed Truth that he saw them in a car and caught them in bed together, but Robin stated on a 2019 episode of Watch What Happens Live with Andy Cohen that he never caught them in bed together and when in the car, they were "coming from like a screening or something."
Christina Applegate
© Getty ImagesChristina Applegate recalled in an interview with More magazine that Brad and his then-roommate Jason Priestly would come over for barbecues when she was starring on Married…with Children and they briefly were an item.
They were pictured together several times, and were each other's dates to the 1989 MTV Video Music Awards, but ended things after Christina revealed she left him for someone else.
Juliette Lewis
© Getty ImagesActress Juliette Lewis dated Brad from 1989-1993, during which time they also starred in the movies Too Young to Die? and Kalifornia. They parted on amicable terms, however, and look back on their relationship fondly.
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Two years after the breakup, the Once Upon a Time in Hollywood star told Vanity Fair: "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."
Gwyneth Paltrow
© Getty ImagesBrad met Gwyneth Paltrow on the set of their 1995 movie Se7en and they quickly became an item, with the actor calling her "the love of my life" during his 1996 Golden Globes acceptance speech.
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Later that year, he proposed while they were in Argentina together, but they called it quits in June 1997 before tying the knot. They remained friends, though, with Gwyneth calling the romance a "love at first sight" situation during a 2023 appearance on Call Her Daddy.
Jennifer Aniston
© Getty ImagesBrad and Jennifer Aniston went on a blind date in 1998 and were engaged the following year. They got married in 2000 in an opulent ceremony, but announced their split in 2005 following rumors of an on-set romance with his Mr. & Mrs. Smith co-star (more on that in a bit).
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In recent years, however, they've become good friends, memorably running into each other at the 2020 Screen Actors Guild Awards and even being seen together at Jen's 50th birthday bash in 2019. During a 2021 appearance on SiriusXM's The Howard Stern Show, she stated: "Brad and I are buddies, we're friends."
Angelina Jolie
© Getty ImagesBrad and Angelina Jolie famously fell in love on the set of 2005's Mr. & Mrs. Smith, but denied any notion of infidelity. They kept their romance a secret till announcing they were expecting their first child in 2006. They announced their engagement in 2012 and were married in 2014 at Château Miraval, the estate they co-owned. The pair dubbed "Brangelina" sadly separated in 2016 and were declared legally single in 2019.
They've since been embroiled in a bitter legal battle over their estate, which has transpired into their relationship with their children and custody. Brad adopted Angelina's son Maddox after they got together, accompanied her to Ethiopia when she adopted Zahara, and then adopted her son Pax. Their daughter Shiloh was born in 2006 and they welcomed twins Knox and Vivienne in 2008.
Ines de Ramon
© ShutterstockAfter being linked with the likes of Neri Oxman, Nicole Poturalski, and Emily Ratajkowski (none of which were confirmed), he began dating jewelry designer Ines de Ramon, who is 26 years his junior.
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They sparked romance reports in late 2022 after being spotted together often, not long after her split from The Vampire Diaries star Paul Wesley. They've made public appearances together but have kept their relationship under wraps, although Ines has reportedly moved in with Brad.
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