In 2020, Paltrow talked to Harper’s Bazaar about where she stood with all her exes. “I’m friendly with Brad Pitt,” the Shakespeare in Love actress said of her Oscar-winning ex-boyfriend at the time. “I don’t have any really bad blood.”
The duo met on the set of the David Fincher film Se7en in 1994 and started dating soon after. They got engaged in 1996, only a few months before their split.
Paltrow talked to radio personality Howard Stern about falling for the Ocean’s Eleven star during a 2015 interview. “He was so gorgeous and sweet. I mean, he was Brad Pitt!” she said at the time, adding that her father, the late director and producer Bruce Paltrow, was “devastated” when they broke up.
Pitt reflected on his relationship with Paltrow’s father during a June 2022 interview with the Goop founder herself. “I’ll never forget when we were engaged and he [Bruce] came to me one day, his eyes full of tears, and he said, ‘You know, I never really realized what they mean when they say you’re gaining a son. Like, I’m gaining a son,’” the Once Upon a Time in Hollywood actor said.
In the interview, the former couple discussed Pitt’s involvement with a new Goop product, God’s True Cashmere, as well as their failed relationship. Paltrow asked Pitt what her father, who died from oral cancer complications at the age of 58 in 2002, had meant to him.
The Oklahoma native replied that Bruce “did have a profound effect” on his own parenting philosophy. “He carved the way for you guys to be who you are. And I think that’s so important to parenting, you know? So the child is free to find out who they are and what they love and what they don’t,” he said. “You guys were just so free in your conversations. And witty. And intelligent. And funny as f–k.”
Paltrow went on to marry Coldplay frontman Chris Martin in 2003, with whom she shares two children: Apple and Moses. The pair finalized their divorce in 2016 after announcing their “conscious uncoupling” in 2014. The Iron Man actress married television writer and director Brad Falchuck in September 2018.
Pitt, for his part, was married to Jennifer Aniston from 2000 to 2005 and then started seeing Angelina Jolie that year. He married his Mr. and Mrs. Smith costar in 2014 but the two split in 2016. Their divorce has not been finalized though a judge declared them legally single in April 2019. Pitt shares six kids with Jolie — Shiloh, Maddox, Vivienne, Knox, Zahara and Pax — and remains in a legal battle with her for custody of their minor children.
Scroll through for a timeline of Paltrow and Pitt’s relationship: