Hey Girl (2010)

New to Chicago, 'Julie' adapts to single life in the big city while her best friend 'Becka' offers emotional support from her home town in Wisconsin where she desperately doesn't want to be. Julie's perverted landlord 'Mr. Willis' contributes many awkward moments as does the many dates with the wrong men that Julie goes on. Becka's boyfriend, Jason is a small town cowboy who doesn't want to lose his girl so he encourages them both to surprise Julie and move into the small studio apartment with her in Chicago, where chaos ensues.