An Awkward Sexual Adventure (2012)

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 not only 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 not being able to envision bad, boring sex with him for the rest of her life. Rachel convinces him to take the vacation by himself, instead 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. Dandak, a sex machine, sees his role in his mending his friend's broken heart as getting him back in the dating scene. Jordan, however, can only think about getting Rachel back, he believing the best way to be a better lover by getting sex pointers from Dandak and to make Rachel jealous by texting her a photograph of him together with a sexy woman. The woman who obliges his sexy photograph request is Julia Bowe, a stripper he befriends. Due to Dandak's changing circumstance, Jordan turns to sexually-liberated Jules also to be his non-sex sex teacher, he in return helping her manage her dismal finances, she who has no concept of money or its management beyond buying whatever she wants. In Jordan and Jules' not always smooth student-teacher and teacher-student relationships, in what ends up being Jordan and Rachel's truncated week apart, and in Dandak dealing with his new situation, each in the collective may eventually come to the realization of what and who he or she wants in life, the further issue being if they can admit these realizations to themselves and the people that matter.