A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he’ll help her with her crushing debt if she helps him become a better lover. To win back his ex-girlfriend, a conservative accountant enlists the help of an exotic dancer to guide him on a quest for sexual experience, leading him into a world of strip clubs, sensual massage parlors, cross-dressing, and S & M. Thirty-seven year old Winnipeg-based accountant Jordan Abrams, a proverbial doormat of a man, has pined after Rachel Stern since he was twelve. He finally got her to be his girlfriend last year after she being a peripheral or not so peripheral part of his life all these years. Now, in a relationship for a year, Jordan plans on asking her to marry him on a week-long romantic vacation they are taking to Niagara Falls. Rachel decides not to go on the trip but dumps him when he, learning that she isn’t going, asks her to marry him the day before the trip instead. The primary reason she dumps him?: he’s lousy in bed; she’s not able to envision bad, boring sex with him for the rest of her life. Rachel convinces him to take the vacation by himself, instead of hanging out in Toronto with his college friend Dandak, his return from the vacation when they will talk about the break-up in more detail. Dundalk, a sex machine, sees his role in mending his friend’s broken heart as getting him back in the dating scene.