Jake Gyllenhaal Was Starstruck Meeting Brad Pitt While Working With Jennifer Aniston

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Jake Gyllenhaal is recalling the "lovely exchange" he had the first time he met Brad Pitt -- but it didn't start out that way.

Gyllenhaal revealed in an interview with W Magazine that the encounter happened while on the set of his and Jennifer Aniston's 2002 film, The Good Girl. The dramedy featured Gyllenhaal and Aniston as love interests who also shared racy love scenes. Gyllenhaal would later reveal he also had a crush on her at the time.

That, in and of itself, made things all the more awkward for Gyllenhaal, who, at the time, was only a few years removed from his breakout role in the 1999 film October Sky, and still looking to cement his name in Hollywood.

Enter Brad Pitt, Aniston's husband at the time.

"I was definitely starstruck when I first met Brad Pitt on the set of The Good Girl," Gyllenhaal admitted. "I was working with Jennifer Aniston, who was his wife at the time, and there were a lot of very racy scenes. I remember putting my hand out to shake his, and accidentally hitting the door. He said, so confidently and kindly, 'Well, you have another one. It's all right.'"

Despite the false start, Gyllenhaal said meeting the Fight Club and Ocean's Eleven star couldn't have been more pleasant.

Jake Gyllenhaal
Tim Walker/'W' Magazine

"He was very, very, very sweet to me," said Gyllenhaal, who triggered Taylor Swift fans with his red-themed photo shoot for W Magazine, "and it was actually a really lovely exchange. But, yeah -- I was starstruck."

The Brokeback Mountain star opened up to Howard Stern on his eponymous SiriusXM show last October, calling his experience filming The Good Girl as "torture" because he struggled to overcome his crush on the Friends star.

"It was torture, yes it was, but it was not torture, I mean, come on," Gyllenhaal said of working with Aniston. "It was a mix of both." 

ET spoke with Aniston about Gyllenhaal's public crush back in 2016 when she was married to Justin Theroux. 

"What do I do with that information now? What good does that do me now?" she jokingly asked at the time. "I love that boy." 

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