The Upside (2009)

Following the misadventures of two eccentric personalities, Dee and Jamie the story is a quirky romantic comedy of two well-meaning individuals who meet and fall in love in an especially clumsy manner. Jamie and her friend Arnold are elementary school teachers. While Arnold is laid back and practical, Jamie is fun and easygoing, but has forgotten how to trust. Jamie's insular world is changed when Dee moves into the building where she's parking her camper van. Dee is tall, attractive, and even more fearful and insecure than her. A hopeless mama's boy, Dee is finally moving into his own place at the age of 30 - with his mother's help, of course. Jamie and Janet clash at first meeting, and Jamie's strange personal world is sucked into the even more bizarre reality that exists around Dee and his mother. However, Jamie remains undeterred by his behavior and a flirtatious rapport develops between the two eccentric characters. Meanwhile, Janet begins a torrid and unlikely affair with Jerome, the obnoxious building supervisor. While Dee and Jamie are suffocated with their insecurities and meaningless exchanges, unable to just go for it even though there is an obvious attraction, Jerome and Janet immediately connect in a very lustful, physical way. A complication arises when Karen, the new phys-ed teacher from out of town meets Jamie.