I caught a cute documentary on Showtime this week called "My Date With Drew," which I am adding to the Movies You Might Not Know list.
It's about Brian Herzlinger, a guy in his late 20s knocking around Hollywood taking any kind of job to make ends meet. When he wins $1,100 as a contestant a TV game show pilot, he decides to use the cash to try to get a date with Drew Barrymore, who he had a crush on since he was 10 and saw her in "ET."
He sets a time limit of thirty days to accomplish this, and recruits a couple of friends for assistants. They buy a video camera with the intention of returning it for a full refund before the month is over, and then try to connect with anyone who can get Brian a step closer to his dream, from her "facialist" to the screenwriter on "Charlie's Angels 2." Fully aware of that thin line between fan and stalker, Herzlinger is a likable enough guy that he gets you on his side early and you root for him, even if it means having to put up with an appearance by Corey Feldman.
I won't tell you how it turns out, but there is one strategy that they don't try until very late in the project, which should have seemed obvious to anyone who wanted to get word-of-mouth going.
"My Date With Drew" won awards at a few film festivals in 2004, but I don't know what happened to Brian Herzlinger -- there isn't much more info on him at IMDB.