An odd-but-gifted poet, Evan Merck (Wes Bentley) makes his living writing suicide notes for the soon-to-be departed. So when he meets Charlotte (Winona Ryder), the free-spirited sister of his latest client, Evan has no choice but to lie about his relationship to her late, lamented brother. Curiously attracted by his evasive charms, a smitten Charlotte begins her pursuit, forcing Evan to juggle an amorous new girlfriend, a sarcastic new client (Ray Romano) and an ever-increasing mountain of lies.