Some stories from early careers always make people smile, and Jake Gyllenhaal recently shared one of his own. He opened up about filming intimate scenes with Jennifer Aniston more than twenty years ago—and how surprisingly difficult it was for him.

Back in 2002, Gyllenhaal starred with Aniston in The Good Girl, a romantic drama about two unhappy store workers who form a close connection. It was one of his first major roles, and working with an actress he admired made the experience both exciting and overwhelming. When asked about it on The Howard Stern Show, he didn’t hold back.

Gyllenhaal admitted the love scenes were “torture,” but not for the reason people might expect. He explained that intimate moments on camera are anything but romantic, with dozens of crew members watching every move. Everything is carefully planned, he said, almost like a choreographed dance rather than a natural moment.

The real turning point came when he confessed he had a longtime crush on Aniston. He adored her charm and personality long before they worked together, which made filming close scenes feel even more awkward. He said working beside her was both a dream and a challenge.

Gyllenhaal also shared that Aniston helped make things easier on set. She even suggested using a pillow for their scenes to keep everything comfortable and professional. He remembered the gesture fondly, calling it thoughtful and kind.

Looking back, both actors laugh about the moment now—a reminder that even Hollywood stars face their own shy, human moments along the way.