In his 60 years of life, Brad Pitt has gotten the fuck around. And if I had that face card (hello piercing blue eyes plus impeccable bone structure) and that unmatched resume, I’d do the same. Obviously everyone’s aware of his super high-profile relationships with Gwyneth Paltrow, Jennifer Aniston, and Angelina Jolie, but those famous girlies actually only make up a small fraction of this man’s dating history. To sum it up, Hollywood’s No. 1 Hunk has been with approximately a trillion costars, models, a singer, and randomly, a jewelry company executive — and those are just the women we know about. I’m sure Brad has had his fair share of private romances too.

Someone could literally write a full-length novel about the Bullet Train star’s past relationships. There’s material for eons. However, I don’t feel like writing a whole book right now, so I made my research as concise as possible: Here’s the crucial tea on all of Brad’s casual relationships, engagements, and marriages. You may wanna get comfortable ’cause it’s a lot to absorb.

Brad Pitt’s Dating History

All Of Brad Pitt’s Former Girlfriends And Wives

Sinitta

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Brad and British pop star Sinitta dated from 1986 to 1988. In 2011, she revealed on I’m a Celebrity … Get Me Out Of Here!: “He was fun, he was young and very sweet.” She noted that he had “the most amazing body.” Important detail.

Jill Schoelen

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In 1988 and 1989, the actor had a romance with his Cutting Class costar, Jill and they were reportedly engaged for three months. Apparently, when Brad took a trip to go visit her in Hungary where she was filming a movie, Jill told him that she’d fallen in love with the director of the film. Brutal.

E.G. Daily

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The voice actress and Brad got together after his relationship with Jill ended. In E!‘s Inside Brad Pitt’s Rocky Love Life | True Hollywood Story, E.G. calls him “deep-souled” and “super cute.” They stayed pals after the sparks died down.

Robin Givens

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Robin and Brad met in 1989 when Brad appeared on her sitcom, Head of the Class. They dated after she split from her ex-husband, Mike Tyson, and the boxer loves bringing that up in interviews. He’s clearly peeved.

Christina Applegate

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This is such an iconic couple. Brad and Christina dated in 1989 and he was her date to the 1989 MTV Movie Awards, but Christina was more intrigued by a different guy who was there. They stopped dating after that, LOL. Imagine being able to say “I broke Brad Pitt’s heart.” Crazy.

Geena Davis

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Brad dated his Thelma & Louise costar, Geena, in 1991, according to his former roommate, Jason Priestley. Serious question: Has Brad ever made it through filming a movie without dating a costar?

Juliette Lewis

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The Too Young to Die? and Kalifornia costars dated back in 1992. In 1995, Brad 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.” Deceased.

Jitka Pohlodek

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A bit awkward… Brad and Czech model Jitka dated in 1994 and 1995 and were reportedly still together when he was all “I still love [Juliette]” to Vanity Fair.

Gwyneth Paltrow

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When Brad and Gwyneth played husband and wife in the 1995 thriller Se7en, they fell for each other IRL. It was pretty serious — Brad literally called her “the love of [his] life” in his 1996 Golden Globes acceptance speech. They were engaged but split in 1997 and never made it to the altar. During her epic 2023 Call Her Daddy appearance, Gwyneth called their relationship “major, major love at first sight” and recalled Brad proposing on a balcony of a house they were renting in Argentina. Sigh.

Jennifer Aniston

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Like every breathing person in the ’90s, Brad fell hard for Jennifer. The actors met in 1998 and were married by 2000. In January 2005, they announced their separation, writing that the decision was “not the result of any of the speculation reported by the tabloid media” and that they “happily remain committed and caring friends.” Jennifer filed for divorce a few months later. Fortunately, there’s no bad blood between these now-friends.

Angelina Jolie

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At last, we arrive at the famous Brangelina. This is a messy tale that began with Brad and Angelina falling for each other on the Mr. and Mrs. Smith set in 2004 — while he was still married to Jennifer. The A-listers exchanged vows at their France chateau in 2014 and share six kids: Maddox, Zahara, Shiloh, Pax and twins Vivienne and Knox. Just two years after they got married, Angelina filed for divorce and her rep said in a statement that the decision was “made for the health of the family.” We later found out that their split came after an alleged physical altercation on a private plane.

Nicole Poturalski

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In the summer of 2020, Brad and Nicole, who’s a model, had a casual relationship. They were spotted together at a 2019 Berlin Film Festival party for Once Upon a Time … In Hollywood and also at Château Miraval in France. Ya know, your typical date spots.

Emily Ratajkowski

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Brad and Emily had a petite fling in September 2022 after she split from her sketchy ex-husband, Sebastian Bear-McClard. Bremily was never super serious.

Ines de Ramon

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The actor is reportedly in a relationship with Ines, a jewelry company executive. They were first linked in November 2022 and have been spotted together several times since. 14th time’s the charm, IG??