Jake Gyllenhaal on Meeting Brad Pitt Amid Jennifer Aniston Marriage

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Jake Gyllenhaal, Brad Pitt, and Jennifer Aniston.
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Not his best hour. Jake Gyllenhaal let his nerves get the most effective of him when he met his costar Jennifer Aniston’s then-husband, Brad Pitt, within the early 2000s.

The Guilty star, 41, and the Friends alum, 52, had been working on 2002’s The Good Girl and had “a lot of very racy scenes” collectively. However, Gyllenhaal was extra anxious about his first encounter with Pitt, 58.

“I remember putting my hand out to shake his and accidentally hitting the door. He said, so confidently and kindly, ‘Well, you have another one. It’s all right,’” the Spider-Man: Far From Home actor recalled in W Magazine’s Best Performances issue. “He was very, very, very sweet to me, and it was actually a really lovely exchange. But, yeah — I was starstruck.”

Gyllenhaal beforehand confessed in October 2021 that he had a crush on Aniston whereas taking pictures the movie. “Oh yeah, it was torture,” he stated on The Howard Stern Show of filming intercourse scenes with the actress. “But it was not torture. Come on, it was a mix of both.”

The Morning Show star was married to Pitt from 2000 to 2005. She later moved on with Justin Theroux — after tying the knot in August 2015, they introduced their separation in February 2018. The Fight Club star, in the meantime, was declared legally single in April 2019 amid his divorce from Angelina Jolie, with whom he shares Maddox, 20, Pax, 18, Zahara, 17, Shiloh, 15, and twins Knox and Vivienne, 13.

Following the Once Upon a Time in Hollywood star’s break up from Jolie, 46, he and Aniston rekindled their friendship. She opened up about their relationship in June 2021 after they teamed up for a digital desk learn of Fast Times at Ridgemont High.

“Brad and I are buddies, we’re friends,” she defined on The Howard Stern Show. “And we speak, and there’s no oddness at all, except for everyone that probably watched it and was wanting there to be, or assumed there to be.”

As for Gyllenhaal, he has one other attainable connection to Aniston. Fans speculated in November 2021 that his ex Taylor Swift referred to the Horrible Bosses star within the 10-minute model of her music “All Too Well,” which is extensively believed to be concerning the Grammy winner’s breakup from the Brokeback Mountain actor.

“Now I’m weeping in a party bathroom / Some actress asking me what happened, you / That’s what happened, you,” Swift, 32, sang on the monitor, as followers pointed to a January 2011 report that claimed Aniston supplied the songwriter recommendation on the People’s Choice Awards shortly after her break up from Gyllenhaal.

However, Aniston’s pal Jennifer Meyer shut down the rumors in November 2021, commenting on an Instagram publish, “NOT TRUE PEOPLE!!! YOU HAAVE [sic] THE WRONG ACTRESS.”

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