My Date with Drew (2005)

My Date with Drew is the kind of scrappy, big-hearted documentary that reminds you why movies make people dream in the first place: it turns a wildly improbable wish into a real, funny, and surprisingly moving journey. With nothing but a camera, a shoestring budget, and an earnest streak a mile wide, Brian Herzlinger invites you into a quest that feels both ridiculous and deeply relatable, capturing the awkward grace of trying hard when the odds are laughing. The vibe is light, playful, and genuinely warm, the humor coming not from cruelty but from the absurdity of the mission and the sincerity behind it. If you prefer sleek, polished docs, the DIY rough edges might not be your thing—but if you like authenticity and an underdog you can’t help rooting for, this is a delightful watch.

My Date with Drew is clearly trying to be a scrappy, feel-good DIY documentary about chasing an impossible dream and turning a personal obsession into a filmmaking experiment. The problem is that the “romantic” premise can read less like charming persistence and more like uncomfortable entitlement, with moments that feel manipulative or self-promotional rather than genuinely heartfelt. On top of that, the home-movie roughness and thin narrative may test your patience if you want a documentary with real depth or broader stakes. If you can enjoy it as a time-capsule of early indie hustle and root for the audacity more than the ethics, there’s some earnest energy here—but if “creepy” celebrity-chasing vibes are a dealbreaker, skip it.