In the 1990s, Gay and Lesbian activists began stamping their dollars to prove they contributed to the American economy. This is the story of one of those dollars. A routine visit to the local convenience store turns out to be an adventure for Pete, a shy teenager who finds himself the unlikely "best bud" of a giant lesbian dollar bill named Evelyn. When Pete's best friend Ben takes a liking to Evelyn, Pete must figure out a way to spend her in this irreverent teenage bromantic comedy.

Two lesbian hookers wind their way through a world of bargain-hunting housewives and double-dealing conservative women in this buddy comedy, an homage to and riff on iconic male hustler films. Margaret is a down-on-her-luck hooker in training, who meets up with Jo, a beautiful and self-assured grifter from a wealthy family and an expert on servicing women, even as she considers herself proudly heterosexual. The film follows their adventures together on the street, through encounters with husky-voiced seductresses, mumbling erotic accessory salesmen and shopaholic swingers. Navigating the bizarre fetishes and sexual needs of their 'dates' brings into focus the hilarious and pathetic disparity between the two hookers, fellow travelers who will share the road together but only for a while.