"Dear Wendy" is set in a nondescript small town in America. It tells the story of Dick Dandelion (Jamie Bell), an adolescent who stays to himself, and can't seem to please his dad who'd rather he just get a job in the mines. But when his father dies, Dick finds himself obsessively drawn to a toy gun. This inspires him to start an exclusive club for other gun enthusiasts, his oddball friends, Stevie (Mark Weber), Huey (Chris Owen), Susan (Allison Pill) and Freddie (Michael Angarano). The club, which meets in the town's mine, is called The Dandies, and each member calls their gun their "partner". They vow to stick to a complicated set of rules detailing when and how they may fire their weapons. The conflict arises when Sheriff Krugsby (Bill Pullman) gets the idea to enlist Dick to help him with delinquent Sebastian (Danso Gordon), with unexpected consequences.