Before her big break, when she was 33, Pompeo auditioned for the film Moonlight Mile where she was introduced to Jake Gyllenhaal, who was only 21. “I was…in the waiting room and the director, and this guy, Jake Gyllenhaal, who I had never heard of – no one had ever heard of him at this point – walked past me.” She added Gyllenhaal proceeded to hit on her, which she said made her feel uncomfortable because he was so young. She later said, “It was the best thing that happened to me all week – to say the very least… I was so flattered. I thanked him and told him how much I hoped we would have a chance to work together one day.” Sure enough they were both cast and worked together on 2002’s Moonlight Mile.
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