You feel sorry for the two leads in this film, and it has nothing to do with their respective characters. No, you sympathize with Sarah Polley ("The Sweet Hereafter") and Eric Thal because they both try so hard to make the most of poorly-written roles. Josephine is a college student and aspiring journalist. Joe is a wiretapper masquerading as a phone company technician. They meet in a bar. She's intrigued and pursues Joe, but Joe plays it cool. They finally get together, have a night of bland sex (bland to the viewer, anyway) and begin a complicated relationship. She finds out about his secret occupation, and continues to date him. He has no people skills whatsoever, and embarrasses Josephine in front of her friends. She continues to date him. It's not until much later in the film that she comes to her senses and realizes what a jerk Joe is. It's a variation of Roger Ebert's idiot plot. The story continues only because both characters are too stupid to realize they're hopelessly wrong for each other. "Joe's So Mean to Josephine" wastes the talents of Polley and Thal. On the bright side, it was nice to see the city of Toronto actually playing itself this time, instead of pretending to be New York or Chicago.