Gwyneth Paltrow reportedly felt “sad” upon learning that Brad Pitt had married Jennifer Aniston, according to Amy Odell’s biography Gwyneth: The Biography.
During a September 2000 interview at the Toronto Film Festival, a “gossipy reporter” asked the Shakespeare in Love actress how she felt about Pitt’s recent wedding to Aniston, which had taken place in July of that year. “‘Are you really asking me this question?’ Gwyneth replied, her eyes now ‘daggers.’ ‘I can’t comment on this kind of thing,’” an excerpt from the book reveals, as reported by Us Weekly.
Behind closed doors, however, Paltrow allegedly shared her true feelings with close friends. “In reality, Gwyneth confided to friends that she’d felt sad when she learned they were getting married. (She was also fond of telling them that Brad ‘has terrible taste in women.’)”
Later that same year, Paltrow appeared to make another pointed remark about Pitt during a business dinner with Estée Lauder heiress Aerin Lauder. “At one dinner, the two were talking about Brad Pitt. According to someone familiar with the discussion, Gwyneth allegedly told her, ‘He’s dumber than a sack of s**t,’” the book claims.
Paltrow and Pitt began dating in 1994 after meeting on the set of Se7en, but their relationship had its complications. During filming for Emma, Paltrow began questioning whether Pitt was the right partner for her. “During Emma’s filming, Gwyneth expressed doubts to one crew member that Pitt was right for her, and admitted that she had a crush on Hugh Grant,” another passage states.
She also opened up about their differences in an interview: “‘Brad and I had very different upbringings,’ she told an interviewer. ‘So when we go to restaurants and order caviar, I have to say to Brad, 'This is beluga and this is osetra.'”
Though the couple got engaged in 1996, they ended their relationship the following year. According to the book, they never publicly shared a “concrete reason for their breakup.”
After the split, Pitt began dating Aniston and proposed in 1999. The two wed in a lavish ceremony in Malibu on July 29, 2000. Their marriage lasted five years, ultimately ending in divorce after Pitt became involved with Mr. and Mrs. Smith co-star Angelina Jolie.
Following Pitt, Paltrow dated actor Ben Affleck. According to Odell’s biography, he was “struggling with alcoholism and a gambling habit” when they met in 1997. Their relationship lasted just over a year before they parted ways.