In one of Hollywood's biggest what ifs, Gwyneth Paltrow was once engaged to be married to Brad Pitt. It wasn't meant to be, however, with the "Shakespeare in Love" star reportedly breaking things off. She and Pitt were eventually able to mend fences, forming a friendship that even Paltrow's current husband Brad Falchuk approves of. That said, things were still pretty tense in the immediate aftermath of the A-listers' 1997 breakup, particularly once Pitt married "Friends" star Jennifer Aniston in 2000.
In fact, despite the fact that Paltrow blames herself for her split from Pitt, the Oscar winner apparently threw some serious shade at her ex and his new wife back in the day.
In Amy Odell's book "Gwyneth: The Biography," the author revealed that while Paltrow declined to publicly address her past relationships, the Goop founder's private comments were scathing. According to Odell, Paltrow was distraught when she learned that Pitt and Aniston were getting married, which is obviously perfectly understandable. However, she frequently told her friends that the "Fight Club" star had "terrible taste in women" too. In fact, during a dinner with New York socialite Aerin Lauder, Paltrow reportedly scoffed that Pitt was "dumber than a sack of s**t."
Of course, Pitt and Aniston weren't built to last either, and the beloved celebrity couple ultimately divorced in 2005. Happily, much like how Paltrow managed to bury the hatchet with Pitt, she did the same with Aniston, and the two are now good friends. The nineties icon even dished to Vanity Fair in 2025 that they occasionally exchange stories about Pitt, quipping, "How can we not? We're girls."
Read more: All Of Brad Pitt's Failed Relationships: A Timeline
Why Did Gwyneth Paltrow And Brad Pitt End Their Engagement?
If you're wondering what exactly led to the abrupt end of Gwyneth Paltrow and Brad Pitt's engagement in the first place, well, on multiple occasions, the "Shallow Hal" star has cited the age gap between the two (Pitt is nine years older than her) as a deciding factor, as well as the fact that she simply wasn't ready for marriage yet. "I was 22 when we met. [...] You can't make that decision when you're 22 years old," Paltrow reasoned in a 2015 chat with Howard Stern, per Vanity Fair. She echoed this sentiment during her 2023 appearance on the "Call Her Daddy" podcast, admitting that she still felt like "a kid" while dating the Oscar winner, and thus "had a lot of development left to do." And yet, Amy Odell reckons that there was something else at play too.
"[Pitt] was brought up very religious, in Missouri," Paltrow's biographer pointed out to People shortly before the release of her book. "It's just a very different world from [Paltrow's], growing up in Manhattan, going to [The] Spence [School], I think she thought he wasn't sophisticated enough for her. She thought she was smarter, better educated, more sophisticated." Odell also claimed that Paltrow had confided in a crew member on the set of her 1996 movie "Emma" that she wasn't sure if things were going to work out with Pitt in the long run, adding that she was crushing on Hugh Grant, who is a few years older than the "Se7en" star, funnily enough. But whatever the whole truth is, all parties involved seem to have moved on in the years since.
Read the original article on The List.
