Nothing ever goes quite as planned for Westley Little (Sean Kaufmann). Wes, a meek and mild insurance broker, sets out to impress his girlfriend, Jennifer (Vanessa Broze), with a surprise romantic evening. Unfortunately, he gets shut down and he is left feeling embarrassed and exposed. In an effort to win her affection, Wes plans a weekend getaway in cottage country for them and some friends. This time, however, not only do his plans go off track, he learns a devastating piece of information about his girlfriend that sends him over the edge. He decides to enlist the help of some old friends to make him look heroic and desirable. The weekend getaway doesn’t go as planned, full of a series of unfortunate, morbidly, and amusing events.