Jake Gyllenhaal: I Had a Crush on Jennifer Aniston for Years

Jake Gyllenhaal poses with Jennifer Aniston at “The Good Girl” premiere in 2002. (Photo: Getty Images)

Jake Gyllenhaal wasn’t, as the song goes, always there for Friends. However, the actor confesses that he had a soft spot for Jennifer Aniston, one of the sitcom’s stars, long before he played her love interest in the 2002 indie movie The Good Girl.

The Demolition actor was asked about several of the people he’s shared the screen with, including Aniston, as part of The Jess Cagle Interview, hosted by the editorial director of People and Entertainment Weekly.

“She’s a rough one,” Gyllenhaal, 35, joked about Aniston, who’s 11 years older than him. “Not likable. So hard to compliment."

Then, Gyllenhaal — who’s exes include Reese Witherspoon, Kirsten Dunst, and Taylor Swift — got seriously flustered.

"I will say, I had a crush on her for years. And working with her was not easy,” Gyllenhaal answered. “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."

Cagle asked if the crush developed while watching Aniston as Rachel Green.

"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 just who she is."

Sounds like someone is still carrying a torch! Gyllenhaal never found love with Aniston, and she married actor Justin Theroux in August. (He’s reportedly single or dating every woman who’s ever been seen with him.)

Five years after Gyllenhaal worked with Aniston, he dated Reese Witherspoon for three years, beginning when both were cast in the 2009 drama Rendition. So, of course, he was asked about her.

Witherspoon and Gyllenhaal broke up in 2009. (Photo: Eric Charbonneau/Getty Images)

"She is, as I would say about most of the women who I’m close friends with or had relationships in my life, one of the smartest, strongest people I’ve ever met,” he said.

Gyllenhaal also clarified that he and Witherspoon never actually shared any screen time.

Related: Jake Gyllenhaal: I’ve Been in Love Three Times

However, he worked twice with Anne Hathaway, whom he never dated. His opinion of his leading lady in Brokeback Mountain and Love and Other Drugs is glowing as well.

Gyllenhaal and Hathaway promote their dramedy. (Photo: Theo Wargo/WireImage)

“A massive talent, and a really brilliant and sometimes confusing human,” he said about Hathaway. “She’s one of the most adventurous people I’ve ever met. … When I first met her, and even now, even knowing her for a long time, Anne is somebody who would just not really want to get into the party — she is the life of the party and the person who will jump off the cliff first. She really is! I love contradictions in people, she happens to be that. I think she’s probably one of the most talented actresses of our generation.”