Jake Gyllenhaal Recalls Awkward Meeting With Brad Pitt Amid Jennifer Aniston’s Marriage

Jake Gyllenhaal recently opened up about an awkward exchange he had with Brad Pitt during the time the actor was married to Jennifer Aniston. In 2002, Gyllenhaal starred in the romantic-dramedy The Good Girl with the former , as part of a pair of characters that begin an affair that has deeply lasting ramifications. It was around this time, Gyllenhaal tells W Magazine for the Best Performances issue, that he had an embarrassing encounter with Pitt.

“I remember putting my hand out to shake his and accidentally hitting the door,” the Spider-Man: Far From Home star remembered. “He said, so confidently and kindly, ‘Well, you have another one. It’s all right.’” Gyllenhaal added, “He was very, very, very sweet to me, and it was actually a really lovely exchange. But, yeah – I was starstruck.” Notably, in 2021, while speaking to Howard Stern, the actor shared that he had a “crush” on Aniston during the Good Girl days, which contributed to acting in sex scenes with her feeling like “torture.” 

“But it was also not torture. I mean, come on, it was like a mix of both,” he said. “Weirdly, love scenes are awkward, because there are maybe 30, 50 people watching it? That doesn’t turn me on.” He went on to describe the process of shooting sex scenes as “oddly mechanical.” Elaborating, Gyllenhaal likened it to a “dance” between actors. “You’re choreographing for a camera. You can get in it, but it’s like a fight scene, you have to choreograph those scenes.” 

The Zodiac actor also shared that they used something called “the pillow technique” to help them be more comfortable. “That was just pre-emptive and used generally always when actually in a horizontal place in that movie,” Gyllenhaal said. “I think that was actually a Jennifer suggestion. She was very kind to suggest it before we began. She was like, ‘I’m putting a pillow here.’”

In big career news for Gyllenhaal, it was recently reported that he’s being considered for the lead role in MGM’s Road House reboot. According to Deadline, sources have said that MGM is very eager to get a new version of the film into production, and have begun looking for scribes to do a re-write on a previous script. Gyllenhaal and director Doug Liman are both attached to the project and, while the two have other films they are starting work on soon, the studio is said to be placing a high priority on the new reboot film.