Everybody loves Drew Barrymore. But face it - she's not a great actress. People like Barrymore (Fever Pitch, 50 First Dates) because they got to watch her grow up. She's cute, highly personable, and looks like a lot of fun to be around. Moreover, everybody got to watch her get past some bad personal problems. What's not to like? Brian Herzlinger has had a crush on her ever since he was a little boy. They are about the same age, and it was crush at first site. Herzlinger always wanted to go on a date with Barrymore. Now, he's living in Hollywood, trying to make it in the movie business. My Date with Drew has a reality show-like premise - Herzlinger has thirty days and $1,100 to get a date with Barrymore.

Herzlinger decided to make a movie out of it. It's a great vehicle for self-promotion (a la Morgan Spurlock's infinitely better Super Size Me), as well as a potential way to fulfill his childhood fantasy. Herzlinger's rules come from his lack of money. He won the $1,100 from a game show, where the final answer was "Drew Barrymore." He saw this as a sign. Circuit City has a thirty-day return policy, so Herzlinger and his friends Jon Gunn (Mercy Streets) and Brett Winn buy an expensive digital camera with the intention of returning it at the end of the month. The trio then attempts to harness the power of 'six degrees of separation,' doing the best they can to use their connections to reach Barrymore.

There is a fine line between fandom and stalking, and Herzlinger is acutely aware of this. He seems like a nice guy, but does sometimes come across as a bit creepy when he pines about his crush. Otherwise, he seems like a normal guy with a hint of dorkiness. Would Barrymore like him? Sure, why not. But as most people know (well before it was mentioned in the film) she was in a committed relationship. He does seem a bit off; after all, what's the big deal? Shouldn't he worry about other things like getting a job? As a result, but bulk of the film is Herzlinger, trying hard to make everything sound more important than it is. He has a strong personality that becomes tiring, especially after seeing how seriously he takes everything, but My Date with Drew does have its moments.

It is impressive how far Herzlinger and company are able to go just on connections. They reach people who are important, like John August, who wrote Charlie's Angels: Full Throttle, and people who are not, like Corey Feldman. Throughout it all, Herzlinger has an optimistic view (or is it ignorance is bliss?) that he is drawing ever closer to his goal. Now, the entire thing is pretty stupid, but it is hard to avert one's eyes from watching (like most reality television). The film moves at a jaunty pace, counting down the days until the return policy runs out. Herzlinger gets tantalizingly close at times, but again, it does often seem like a big fuss about nothing. My Date with Drew does not approach the level of train-wreck watchable, but sometimes comes close.