I Probably Shouldn't Have Done That chronicles the series of vast, at times incomprehensible, mistakes that Jules makes in an attempt to get over her first "serious" boyfriend. It follows her through drunken nights, drunker nights, bad dates, worse dates, encounters with her ex, and a very few glistening moments of hope and self-realization.

It is a thoroughly sad break-up story, an occasionally naive love story, and a comical train wreck throughout.