jennifer aniston and pitt


Movie stars—they’re just like us. When it comes to meeting A-list celebrities, we can’t help but feel just a tad intimidated. But to say that Jake Gyllenhaal became nervous when meeting Brad Pitt for the first time would be a colossal understatement.



Some 20 years ago, Gyllenhaal, 41, was filming 2002’s The Good Girl with Pitt’s then-wife, Jennifer Aniston, 52. Some of the comedy-drama’s plot was about an affair, and, obviously, included sex scenes between their characters. For the Spiderman: Far From Home actor, filming the “racy scenes” with Aniston was no problem, he told W Magazine. But when it came to meeting Pitt, 58, on the movie set, he was pretty anxious. By then, the Fight Club actor already had some major credits under his belt and was massively famous.



jennifer and brad pitt regrets
“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,’” he said of Pitt’s response. “He was very, very, very sweet to me, and it was actually a really lovely exchange. But, yeah — I was starstruck.”



Back in October 2021, Gyllenhaal also admitted on The Howard Stern Show that he had a crush on the Friends actress while they were shooting The Good Girl, according to Us Weekly. “Oh yeah, it was torture,” he said, recalling his early career as a 22-year-old. “But it was not torture. Come on, it was a mix of both.”



jennifer aniston dating
Aniston stayed married to Pitt until 2005, then later married Justin Theroux, 50, but they separated in February 2018. On the other hand, the Once Upon a Time in Hollywood actor went on to marry Angelina Jolie, 46, in 2014, but officially divorced her in April 2019. The two share children Maddox, 20, Pax, 18, Zahara, 17, Shiloh, 15 and twins Knox and Vivienne, 13.



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