After his long-time girlfriend dumps him, a thirty-year-old record store owner seeks to understand why he is unlucky in love while recounting his "top five breakups of all time".

Hitman Martin Blank becomes a moving target after he rebuffs a fellow assassin's invitation to form a union. On the advice of his quirky assistant and neurotic psychiatrist, Martin begrudgingly heads out to Grosse Pointe, Michigan for his ten-year high school reunion, where he soon comes across the woman he jilted on prom night.

In the future, the desert country of Turaqistan is torn by a riot after private corporation Tamerlane, owned by the former Vice President of the United States, has taken over. Brand Hauser, a hitman who suppresses his emotions by gobbling down hot sauce, is hired by the corporation's head to kill the CEO of their competitors.