Jake Gyllenhaal's First Encounter With Brad Pitt Was Downright Embarrassing

Actor Jake Gyllenhaal has become a household name through his roles in "Brokeback Mountain" and "Nightcrawler." In 2020, he opened up to Vogue about his passion for the industry. "I do love acting in movies and I have had great luck, but really I feel at home when I'm acting and singing simultaneously. It's been that way since I was very young," he said.

Although he has made headlines in recent months, through the resurgence of his relationship with Taylor Swift and the re-release of "Red (Taylor's Version)," he hasn't seemed very phased by the news. However, that hasn't stopped Gyllenhaal by being embarrassed in other ways. Even The Independent was inspired to make a list of his weirdest moments, from admitting he doesn't shower to his appearances with "Spider-Man" co-star Tom Holland.

Now, the actor has been the subject of another embarrassing encounter, this time with another A-list movie star.

Brad Pitt wasn't phased by Jake Gyllenhaal's clumsiness

During a new interview with W Magazine, actor Jake Gyllenhaal reflected on his first time meeting Brad Pitt: on the 2002 set of "The Good Girl." According to Gyllenhaal, Pitt popped into the set to support his then-wife Jennifer Aniston, before the pair had an incredibly awkward encounter.

"I remember putting my hand out to shake his, and accidentally hitting the door," Gyllenhaal said. Instead of being phased by the mishap, Pitt had a sense of humor. "He said, so confidently and kindly, 'Well, you have another one. It's all right.' He was very, very, very sweet to me, and it was actually a really lovely exchange. But, yeah—I was starstruck."

However, the interview alone isn't the only thing raising eyebrows among fans, as many on social media point out the potential inspiration behind Gyllenhaal's W photoshoot. As the magazine initially captioned on Instagram along the lines of "Jake's Version," the actor is eerily dressed in all red and what appears to be Taylor Swift-inspired sunglasses, similar to hers in the "22" music video.