My Awkward Sexual Adventure

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 …