When Charlie Carroll (Tveit) quits his job and his girlfriend (Elliott) on the same day, it seems as though he’s finally found freedom. But after a quick dip in the dark waters of the NYC dating pool, Charlie begins to wonder if he’s made a mistake. He’s not equipped for single life. In fact, Charlie might not be equipped for life in general. With no job and no love, Charlie is forced to go on a journey of self-discovery so intense that he begins to suffer from surreal hallucinations, flashbacks, and fantasies. Will he find “the one?” Or did that ship already sail, taking with it his only hopes for relationship sanity?