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.

Washington, DC, 1935: At the height of the Great Depression, a charming and irrepressible young thief is forced to help an icy and mysterious United States Navy spy steal a brand new device that the Japanese military is using to encode its top-secret messages. During the mission, which is complicated by the spy's dark past in Tokyo, the two discover that they are pawns in a larger game. Together, they devise an intricate but risky scheme to outwit the people trying to use them.