My Date with Drew (2005)

Ever since the second grade when he first saw her in E.T. The Extraterrestrial, Brian Herzlinger has had a crush on Drew Barrymore. Now, 20 years later he's decided to try to fulfill his lifelong dream by asking for her a date. There's one small problem: She's Drew Barrymore and he's, well, Brian Herzlinger, a broke 27-year-old aspiring filmmaker from New Jersey. But that doesn't stop Brian and his film school pals from doing everything they can think of to convince Barrymore to go out with him--and documenting their quest along the way. Equipped with a video camera they have to return to Circuit City in 30 days and the $1,100 Brian won on a game show (where the winning answer was, prophetically, "Drew Barrymore"), they've got one month to accomplish their mission. To succeed, they'll need to negotiate an army of publicists, agents, producers and assistants who surround the star so Brian can pop the question.