Jake Gyllenhaal Had Awkward Brad Pitt Encounter Amid Jen Aniston Marriage

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

Brad Pitt and Jennifer Aniston’s Relationship Timeline

The Guilty star, 41, and the Friends alum, 52, were working on 2002’s The Good Girl and had “a lot of very racy scenes” together. However, Gyllenhaal was more 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 previously confessed in October 2021 that he had a crush on Aniston while shooting the film. “Oh yeah, it was torture,” he said on The Howard Stern Show of filming sex scenes with the actress. “But it was not torture. Come on, it was a mix of both.”

Justin! Brad! A Timeline of Jennifer Aniston’s Dating History

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 announced their separation in February 2018. The Fight Club star, meanwhile, 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 split from Jolie, 46, he and Aniston rekindled their friendship. She opened up about their relationship in June 2021 after they teamed up for a virtual table read of Fast Times at Ridgemont High.

“Brad and I are buddies, we’re friends,” she explained 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.”

Looking Back at Jake Gyllenhaal’s Dating History

As for Gyllenhaal, he has another possible connection to Aniston. Fans speculated in November 2021 that his ex Taylor Swift referred to the Horrible Bosses star in the 10-minute version of her song “All Too Well,” which is widely believed to be about 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 track, as fans pointed to a January 2011 report that claimed Aniston offered the songwriter advice at the People’s Choice Awards shortly after her split from Gyllenhaal.

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

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