'Working with her was not easy,' Gyllenhaal joked to PEOPLE and EW editorial director Jess Cagle
Credit: Jeff Vespa/WireImage

Jake Gyllenhaal has starred with some of Hollywood’s biggest actresses throughout his career — everyone from Anne Hathaway to Rene Russo to Rachel McAdams to Natalie Portman to Reese Witherspoon. But it was Jennifer Aniston, Gyllenhaal’s costar in The Good Girl, who left the actor almost speechless.

“She’s a rough one. Not likable. So hard to compliment,” Gyllenhaal joked to PEOPLE and EW editorial director Jess Cagle in the latest edition of The Jess Cagle Interview.

Gyllenhaal was 21 years old when The Good Girl came out, and the film found him playing Aniston’s onscreen love interest. “I will say, I had a crush on her for years. And working with her was not easy,” Gyllenhaal said of making the film with Aniston. “I was — um, yeah. That’s all I’m going to say. It was lovely. It wasn’t hard, that’s what I would say.”

Now 35, Gyllenhaal says it wasn’t Friends that put him on Team Aniston, but the way the actress presented herself both onscreen and off.

“Not so much Friends, but kind of her personality from afar, and movies she was in,” he said. “And some of Friends — I’m not a huge Friends fan — but who she is.”

Watch Gyllenhaal discuss Aniston with Cagle in the video segment above, and check out the full interview with Gyllenhaal below.

Gyllenhaal stars in the new film Demolition, from director Jean-Marc Vallée (Wild), out in theaters this week