For years, Brian Herzlinger has had a crush on a pretty girl. There's nothing so strange about that, or even that the girl in question is the famous actress Drew Barrymore. What is unusual is that Herzlinger decided to do something about it. Herzlinger was flat broke and out of work when he won 1,100 dollars on a game show, and decided it was time to make his dream come true - and make a movie about it at the same time. Herzlinger and a friend bought a high-end video camera at an electronics store with a 30-day, "no questions asked" return policy, and with his 1,100-dollar bankroll, they set out to find a way to meet Drew Barrymore and have Brian take her out on a date before they ran out of cash and had to return the camera. My Date with Drew is the document of Herzlinger's struggle to live out a regular guy's dream.