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The one that got away. For both, perhaps?
"I f--ked that up, Brad," Paltrow said on the Girlboss Radio podcast when host Sophia Amoruso mentioned Gwyneth's great love of the mid-'to-late-90s, whom she met in 1994 on the set of the thriller Se7en, playing his ill-fated wife.
When he won a Golden Globe for 12 Monkeys in 1996, Pitt's final thank you was reserved for "especially the love o' my life, my angel, Gwyneth Paltrow." They got engaged, they even got matching haircuts, but then they broke up in June 1997.
Paltrow has been relentless in blaming herself for the demise of their relationship, telling Diane Sawyer in 2003, "I'm so lucky that I spent time with Brad, somebody who was such a good person! Especially when I was, like, such a mess." Admittedly the relentless media attention—which peaked when long-lens nude photos of the couple taken while they were vacationing in the Caribbean ended up online—really got to her then, understandably so.
"My kind of internal stuff really tripped up that whole relationship," Paltrow said. "And I felt really responsible, and also like I was the architect of my own misery...I just made a big mess out of it.''
The actress told Howard Stern in 2015 that her beloved father, Bruce Paltrow, who died in 2002, "adored him like a son." But "I was such a kid, I was 22 when we met. It's taken 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."
Only recently did Paltrow tell the New York Times that she too was subject to unwanted advances from alleged serial predator Harvey Weinstein roughly 20 years ago, when she was dating Pitt—and that Pitt confronted Weinstein at an event afterward, warning the producer that something like that had best never happen again. So there was more going on at the time for Paltrow to process than anyone publicly knew about for decades.
By the time of the Sawyer sit-down, Pitt was married to Jennifer Aniston. "We're able to sort of see each other and smile and wish each other well," Paltrow said.