According to Amy Odell's new biography, Gwyneth: The Biography, Gwyneth Paltrow reportedly felt "sad" when she learned that her former fiancé, Brad Pitt, had married Jennifer Aniston in 2000. Paltrow and Pitt's relationship began in 1994 after meeting on the set of Se7en and were engaged in 1996, but they ended their relationship in 1997. The book reveals that Paltrow confided in friends about her feelings regarding Pitt's marriage to Aniston.

In September 2000, during an interview at the Toronto Film Festival, Paltrow was asked by a reporter how she felt about Pitt's marriage to Aniston, which had occurred in July of that year. According to an excerpt from the book, Paltrow responded with visible annoyance, her eyes turning "daggers," and stated, "Are you really asking me this question? I can't comment on this kind of thing". However, the biography claims that, in reality, Paltrow told friends she felt saddened by the news. She also reportedly told them that Pitt "has terrible taste in women".

Later that year, Paltrow allegedly made another critical remark about Pitt during a business dinner with Estée Lauder heiress Aerin Lauder. According to someone familiar with the discussion, Paltrow purportedly said, "He's dumber than a sack of s--t". Odell suggests that Paltrow's feelings toward Pitt were rooted in their different backgrounds. She felt that Pitt, who was raised in Missouri with a religious upbringing, lacked the sophistication she desired, having grown up in Manhattan. In an interview, Paltrow said that "Brad and I had very different upbringings," and gave an example: "When we go to a restaurant and order caviar, I have to explain to him which is beluga and which is sturgeon". Despite these feelings, Paltrow's family, especially her late father, Bruce Paltrow, adored Pitt.

Pitt and Aniston were married for just over five years, having tied the knot in a lavish ceremony in Malibu on July 29, 2000. They announced their separation on January 7, 2005, and were divorced less than nine months later. Following Pitt, Paltrow dated Ben Affleck, and their relationship lasted a little over a year. Paltrow later married Coldplay frontman Chris Martin in 2003, and they had two children before separating in 2014. Paltrow is currently married to writer and director Brad Falchuk, whom she wed in 2018.