Gwyneth Paltrow and Brad Pitt eventually reconciled their friendship, yet the news of his July 2000 marriage to Jennifer Aniston, a few years after their own engagement had ended following their "Shakespeare in Love" days, didn't sit entirely comfortably with her. According to Amy Odell's "Gwyneth," a recent biography on the actress and Goop founder, barely a month into Pitt and Aniston's union, Paltrow was grilled about her feelings regarding their wedding during the Toronto International Film Festival premiere of her film "Duets" on September 9, 2000.
"Are you really asking me this question?" Paltrow quizzically inquired of a Toronto Star reporter, as recounted by Odell. "I can't comment on this kind of thing."
However, behind closed doors, the Oscar-winner confided in friends that she felt a pang of sadness upon learning of Pitt and Aniston's engagement, as revealed in the book. Odell further wrote that Paltrow took delight in jesting with her pals about Pitt's supposed "terrible taste in women."
Nevertheless, it was an open secret that her split from Pitt had left an indelible mark on her. "It really changed my life," Paltrow confessed to Vanity Fair for its September 2000 cover story. "When we split up, something changed permanently within me... My heart broke that day, and it will never be the same."
Her alleged remark about Pitt's taste could have easily been a self-deprecating jab at herself. "I think you have to keep yourself intact to have a healthy relationship, and I didn't. I loved every second of it, but it wasn't healthy," she told VF. "But I wouldn't change anything. Even the things I hate most about myself for what happened—the darkest moment of it—I wouldn't change. Because it's made me what I am."
Years hence, Paltrow candidly revealed that she was the one who wasn't mentally prepared when Pitt proposed. "I was such a kid, I was 22 when we met," she said on The Howard Stern Show in 2015. "It took me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old... I wasn't ready, and he was too good for me."
In 2023, she elaborated on Call Her Daddy, "He was ready to do it and I was kind of all over the place."
Meanwhile, when Aniston first flashed her Pitt-designed diamond at New York's Beacon Theater during a Sting concert in November 1999, Paltrow had been on-and-off dating Ben Affleck for two years. Their relationship permanently fizzled out in October 2000, and two years later, she met Chris Martin. She tied the knot with the Coldplay frontman in 2003 and together they share daughter Apple Martin, 21, and son Moses Martin, 19.
Aniston and Pitt divorced in 2005, but after some time, they mended fences and became friends. Martin and Paltrow consciously uncoupled in 2014, remaining close coparents and occasional trolling partners.
Yet, it was Paltrow and Pitt who joined forces in 2022 to sell $2,000 shirts. "I finally found the Brad I was supposed to marry," quipped Paltrow, who was happily married to Brad Falchuk at the time, during a Goop.com conversation discussing their God's True Cashmere collaboration. "It just took me 20 years."
To which Pitt replied, "And it's lovely to have you as a friend now." When she agreed, he said, "And I do love you." Paltrow added, "I love you so much."
