Rent My Date with Drew (2004)

Since the second grade, Brian has had a crush on Drew Barrymore and now 20 years later he wants to fulfill his dream by asking her on a date. It starts with only two friends, a camera (that has to be returned to Circuit City in 30 days) and $1,100. There's one little problem though: Brian's just an average guy in L.A. - an aspiring filmmaker with no money. He has only one month and knows his chances are slim, but driven by the words of Drew Barrymore herself*, nothing will stop him, not even his mom.