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Jennifer Aniston spills on discussing Brad Pitt with his famous ex


The Friends alum is good friends with her ex's ex-fiancée


Brad Pitt and Jennifer Aniston attend the premiere of "Troy" on May 10, 2004 in New York City© Getty
Beatriz Colon
Beatriz ColonNew York Writer - New York
August 11, 2025
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Jennifer Aniston and Gwyneth Paltrow are just "girls," who sometimes can't help but talk about their — shared — ex.

The Friends alum and the Goop founder have both been proposed to by Brad Pitt, first the latter, who was engaged to the F1 actor from 1996 to 1997, and later the former, who was engaged and later married to him, from 2000 to 2005.

Twenty years later, it's their own friendship that has outlasted both those romances.

GWYNETH PALTROW, JENNIFER ANISTON attend Stand Up To Cancer (SU2C), a program of the Entertainment Industry Foundation (EIF), staging its fourth biennial fundraising telecast at the at the Dolby Theatre on Friday September 5, 2014© Getty
Gwyneth and Jennifer in 2014

In a new cover story for Vanity Fair starring Jennifer, both she and Gwyneth gave insight into their friendship, which began around the time the Shakespeare in Love actress starred opposite Jennifer's Friends co-star David Schwimmer in the 1996 romantic comedy The Pallbearer.

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"Ironically, I went to her and Brad's engagement party," Gwyneth confessed. Brad proposed to Jennifer in November 1999, just over two years after his split from Gwyneth, and they confirmed their engagement at a Sting concert.

Asked whether the two, Jennifer and Gwyneth, still talk about Brad, Jennifer confessed: "Oh, of course," adding: "How can we not? We're girls."

Gwyneth Paltrow and Brad Pitt© Getty Images
Gwyneth and Brad were together from 1994 to 1997

Still, more than about Brad they talk about wellness and health tips. "We're always swapping advice — 'What are you doing for this? What are you doing for that? Do you have a new doctor for that?'" Jennifer further shared.

Both Jennifer and Gwyneth have spoken candidly about Brad, and reunited with him, in recent years, testifying to their friendly relationship with him to this day.

Jennifer Aniston and Brad Pitt make their first red carpet appearance as a married couple at the 2000 Emmy Awards© Getty
Jennifer and Brad made their first red carpet appearance as a married couple at the 2000 Emmy Awards

In a 2022 interview for Goop promoting Brad's line of cashmere clothing, God's True Cashmere, Brad fondly looked back on his relationship with Gwyneth's dad Bruce Paltrow, who passed away in 2002, and how it was him who first introduced him to cashmere. 

"Bruce taught me about cashmere, what a nice bottle of red is — what a fine bottle of wine means and how to experience it. And I really value that. Hanging out with both of you sanded off some of my rough country edges," he said at the time.

Brad Pitt and Jennifer Aniston reunited publicly in 2020 - with the photo going viral© Getty
The former couple reunited publicly in 2020

Further in the conversation, Gwyneth also joked: "I finally found the Brad I was supposed to marry. It just took me 20 years," referring to her now husband Brad Falchuk. Solidifying their love for one another decades later, Brad told her: "And it's lovely to have you as a friend now," before the two exchanged "I love yous."

As for Jennifer and Brad, after reuniting for a virtual, live table reading of Fast Times at Ridgemont High to raise money for Sean Penn's nonprofit CORE (Community Organized Relief Effort) and REFORM Alliance, in September 2020, the former gave an update on their relationship during a subsequent appearance on The Howard Stern Show. "It was absolutely fun. Brad and I are buddies, we're friends," she maintained at the time.

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