My Date with Drew was sadly missed by too many people, including myself, when it was released in 2005. Because of its obscurity, I was concerned about its quality. But within the first ten minutes I was sure there was no need to worry.

Brain Herzlinger is 27, a rather anonymous young man living in Los Angeles who is, in simple terms, broke and unemployed. So he does what any rational person would, he takes the $1,100 he won on a game show and sets out to get a date with Drew Barrymore, filming the whole thing. Ms. Barrymore is an obvious choice for a guy who joined her fan club when he was ten. Oh, and because he can’t afford a video camera, he only has 30 days before he must return it and end his quest.

Herzlinger’s is a fundamentally quixotic quest. But he has no delusions, and his film shows a keen awareness of comical nature his goal. In conveying this story, the film would most easily be called a documentary, but the stodgy image that conjures isn’t really accurate.

In making fun of himself, it’s hard to not get at least a few good laughs out of this film–something better than many comedies manage. In just one example, Herzlinger decides that he needs to be in better shape if he’s ever to win a date with Ms. Barrymore. So, he works out with a trainer friend in a montage ripped straight out of one of the six Rockys, and featuring his curly hair bobbing over his ironic red headband.

Herzlinger and his two friends exhaust every possible means to get to Ms. Barrymore. Their idea is fun, if not the most effective. They’ll play “Six Degrees of Separation” until they find someone to introduce them. This leads them to a number of dead ends, including Barrymore’s cousin–who claims never to have met Drew Barrymore–and the famous but rather unhelpful Cory Feldman.

They also get more innovative. They cut together a trailer for their film and send it to Ms. Barrymore’s publishing company. They create a website to supercharge their six degrees quest. They fake passes to get themselves into the premiere of Charlie’s Angels: Full Throttle.

As you can probably guess, some of these methods work better than others. Throughout, Mr. Herzlinger unselfishly admits many of his struggles, quirks, and insecurities. He constantly worries that he’ll come off as little more than a stalker. It’s refreshing to see such honesty in film, even in documentary–a genre which is supposed to be honest, but is often filled with people’s rosy views of themselves.

I must, of course, concede that the film is not flawless. Sometimes it feels like Mr. Herzlinger’s team is trying to do things the hardest way they can. But if that’s really the case, they hide it well. They seem always to be doing their best–even when it doesn’t appear to be much–to accomplish their goal.

Overall, I think it’s a great film. And though I’d love to tell you how it ends, the closest I’ll allow myself to offer is something Mr. Herzlinger has to say about his quest:

“And for anyone out there thinking of pursuing a lifelong dream: Take the risk. I highly recommend it.”