What he chooses to do with that money is perhaps even more frightening: Rather than use it to pay his rent, to keep the lights on, to feed himself, he instead invests it in a documentary about chasing down a childhood crush in the hopes of going out on a single date with her. What's even more unsettling is the object of his infatuation: Drew Barrymore, with whom Herzlinger has been in love ever since he was a 10-year-old member of her fan club. (He still has the publicity still sent to members, in its original pink envelope, and even now his apartment is decorated with an E.T. movie poster, signed by Steven Spielberg, presumably when Herzlinger met the director during his senior year in high school, in 1994.) With his life's savings and a video camera from Circuit City, which he would return within 30 days, Herzlinger set out in 2003 to track down his prey through friends of friends of friends, including actors Eric Roberts and Corey Feldman and Charlie's Angels screenwriter John August. But, of course, you dare not label him a stalker. His is, after all, an innocent sort of pestering -- the last gasp of a desperate man in search of the elusive dream girl who will make his life seem a little worthwhile.
Of course, you may choose to read My Date With Drew several different ways -- as endearing or frightening, as bleak or expectant, as the optimistic daydream of the naive Everyman or the beginning of a problem that could only lead to a restraining order. Barrymore had her own ideas, revealed at movie's end, but to give away her response would spoil the final and most compelling moments of a movie that keeps trying to convince you its star's obsession is healthy and reasonable. Suffice it to say that Herzlinger could have picked a far worse subject; God only knows how badly things might have gone had he spent a lifetime stalking -- pardon, adoring from afar -- someone far less bubbly, perky, compassionate, and sympathetic than Barrymore.
To be fair, Herzlinger, who looks like a more hirsute version of Gremlins star Zach Galligan, doesn't come across as menacing, only a little lost and a lot goofy. (He's a grown man prone to jumping up and down like a little girl when he receives good news, and he's honest enough to include audio of an ex-girlfriend telling him she asked him out only because she felt sorry for him.) But you can't help but feel a little worried for the guy, precisely because he's put so much into his hunt for Barrymore that he comes perilously close to becoming a fuck-up -- to the point where he almost doesn't go on a job interview with E! Entertainment Television because he doesn't want real life interfering with the pursuit of his fantasy. And Herzlinger's friends only encourage and enable him: They drive him to pick up a $100 check his folks have overnighted him, they help shoot his movie, they make phone calls on his behalf, they cash in favor after favor and connection after connection, and never once lecture him on the need to be the slightest bit responsible.
And they don't lose their shit when Herzlinger actually meets Barrymore at the post-premiere party for Charlie's Angels: Full Throttle and completely freezes up. They've spent hours plotting how to get him in, even making two sets of fake badges that allow him access, and yet when he's introduced to her by the wife of a friend, Herzlinger goes blank, stammers, and wastes the opportunity. It's the ultimate blowing-it moment, a pissing away of so much effort and occasion, yet his pals Joe Gunn and Brett Winn (the doc's co-directors) just let it go. Where most folks would lay into Herzlinger, branding him coward or schmuck or worse, they regroup and press on -- true believers in their buddy's cause, even if he doesn't prove himself up to the challenge during such instances.
Early in the movie, a screenwriter pal of Herzlinger's wishes him nothing but failure on his quest -- "for the sake of America," he says, suggesting that Herzlinger's is little more than the shallow pursuit of a famous person, and he's not far off. After all, it's our national pastime, our collective obsession -- to either be famous or know someone who is. But there is, admittedly, something a little inspiring, too, in watching one man risking everything to see whether he can make a childhood fantasy become reality -- if only for an afternoon. After all, as a wise person once said, "If you don't take risks, you'll have a wasted soul." Oh, wait. That was Drew Barrymore.