One week before proposing to his girlfriend, Kyle, a down-on-his-luck romantic, discovers that she's been sleeping with another man. Unemployed, saddled with debt, and depressed, Kyle embarks on a funny yet affecting journey to recovery that involves living in his car, bottom-of-the-barrel jobs, therapy, online dating, and Kyle's own wild, fantastical, and snarky imagination.

Zak is a smart, good-looking nice guy whose heretofore charmed life starts coming apart as his longtime romance with Samantha, a painter whom he finds increasingly intimidating, begins to crumble; impending graduation makes it clear to her that that she's ready to move on.