"It was lovely. It wasn't hard, that's what I would say," Jake Gyllenhaal said of working with Aniston

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April 06, 2016 11:00 AM

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 Entertainment Weekly editorial director Jess Cagle in the latest edition of The Jess Cagle Interview.

Watch more of The Jess Cagle Interview with Jake Gyllenhaal this week on PEOPLE.com.

Jake Gyllenhaal and Jennifer Aniston
Jeff Vespa/WireImage

Gyllenhaal was 22 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.”

Read more on Jake Gyllenhaal in the new issue of PEOPLE, on newsstands Friday

Drew Barrymore on the cover of PEOPLE

Now 35, Gyllenhaal says it wasn’t Friends that put him on Team Aniston, but the way the actress presented herself. “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.”

Gyllenhaal stars in the new film Demolition out this week; watch more of his interview with Jess Cagle in the clip above.

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