“If you don’t take risks, you’ll have a wasted soul.” So says Drew Barrymore, quite possibly the nicest person to ever work in Hollywood. For 27-year-old Brian Herzlinger these are not just words of wisdom but also words of encouragement. Fixated on Barrymore since she became a child star, Herzlinger wins $1,100 on the game show Taboo thanks to the actress (her name is the winning answer during the program’s final round), an act of fate that motivates him to try and score a date with her in a matter of a month, documenting the experience using a camera from Circuit City he hopes to return just under the wire of the store’s 30-day return policy.
Insofar as the documentary may actually come to a theater near you, it’s difficult not to look at it in the same way most people refused to look at Super Size Me: as an attention-grabbing stunt. Directed by Herzlinger and pals Jon Gunn and Brett Winn, My Date Wit Drew has considerably less to say about the world than Morgan Spurlock’s totem to his lack of self-regard, but it happens to be infinitely more agreeable, if still rather conflicting, at least for me: Herzlinger—who shares my same exact birthday—is an average joe as endearing as his object of affection (for us, the darling Barrymore could be a girl we played with as a child who so happened to make it in the movies), but it’s easy to scoff at his journey in the same way a cynical Bill D’Elia does when he wishes Herzlinger fails for “the sake of America.”
Against all odds, though, Herzlinger moves closer and closer to his goal and Win a Date With Drew reveals itself to be not so much a desperate love letter to a Hollywood starlet but an accidental commentary on the difficult task of reaching out and initiating something resembling genuine human contact through a seemingly impenetrable and guarded web of Hollywood connections. It’s a depressing journey (does Herzlinger even realize that most of the people who grant him interviews—like Corey Feldman and Jenna “Survivor” Lewis—are either has-beens or never-weres?), and though the filmmakers don’t strain very hard to relate Barrymore’s oft-repeated words of wisdom to the dreams of anyone with more in mind than dating a superstar, the film’s charming coda proves to be an affront to D’Elia insofar as America could stand to learn that not everyone in Hollywood is a callous powerplayer.