A darkly comic film centering on an odd-but-gifted poet, Evan Merck (Wes Bentley) who makes his living writing suicide notes for the soon-to-be departed. One day, while attending the funeral of a client Evan meets Charlotte (Winona Ryder) the free-spirited sister of the deceased. Blissfully unaware of Evan’s true connection to her late brother, Charlotte becomes fascinated by the introverted writer and love blossoms between the unlikely pair. Evan finds himself juggling an ever-increasing mountain of lies, an amorous new girlfriend, and a sarcastic new client (Ray Romano).