Rusty is as clueless in love as they come. He gets talked into getting a job as a bartender by his gay friend, Jim, who insists that the bar is the greatest place to work. His entire life changes on his first day on the job when he meets Angel, a twenty-something dating veteran. Taking pity on him, Angel takes Rusty under her wing and shows him the ways of dating the single women of their bustling metropolis, with hilarious results. Rusty develops his incredibly awkward social skills, collects souvenirs from the people he meets, and gains memories that last him a lifetime.