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.
“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.”
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.
Shortly after Pitt’s split from Jolie, the world was ecstatic to see his reunited friendship with Aniston—especially when the two worked together on their virtual table read of Fast Times at Ridgemont High in 2020.
In June 2021, she gushed about their relationship on The Howard Stern Show: “Brad and I are buddies, we’re friends,” she said at the time. “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.”
The star of The Guilty may have had a slightly more difficult 2021. His ex-girlfriend Taylor Swift, 32, released Red (Taylor’s Version), which included a 10-minute version of her 2012 song, “All Too Well,” commonly known by Swifties to have been written about him.
The lyrics may even hint at a run-in with Aniston at the People’s Choice Awards right after the breakup with Gyllenhaal, according to Us Weekly: “Now I’m weeping in a party bathroom / Some actress asking me what happened, you / That’s what happened, you.” But the rumors were shut down immediately. Aniston’s close friend Jennifer Meyer took to Instagram, commenting on a post, “NOT TRUE PEOPLE!!! YOU HAAVE [sic] THE WRONG ACTRESS.”
While it’s impossible to know who the song really refers to, it sure is fun to speculate what goes on in the relationships of celebrities.