Against the advice of his best friend Ted (Michael Weston), Anderson (Jason Biggs) publicly proposes to his girlfriend Vanessa (Audra Blaser), while dressed in a cupid costume. The shock of the unexpected proposal leads to her instantaneous death. Utterly devastated and distraught, Anderson quits his job and goes into mourning. A year later, Anderson is still obsessed with his "perfect" (and dead) former girlfriend. While Ted and Anderson are lunching together in a diner, to help him move on, Ted persuades Anderson to give romance one more try. To placate his friend, Anderson agrees, looks around, and asks attractive waitress Katie (Isla Fisher) to marry him. To both men's utter astonishment, she accepts Anderson's proposal.