It’s Friday afternoon, and Dave McGuiness has a problem. Last night, his longtime girlfriend, Karen, told him that she wants to get married. She’d like an answer by Monday, but Dave’s not sure he’s ready to propose. As Dave starts to share his feelings with family and close friends on the pros and cons of getting married, he learns that the rumor mill is two steps ahead of him. Everyone in the South Suburbs of Chicago already thinks he and Karen are “officially” engaged. Dave’s buddy Marv knows just what will help Dave forget the dilemma for a while. He takes Dave, Dave’s brother Ben and their friend Al out to party on the town all weekend. Marv figures that if this is Dave’s last weekend before he pops the question, it had better be one he won’t soon forget. But Dave figures that if he does marry Karen, he may never get a chance to try something else, and the rest of his life won’t be much more than night after night in these same bars. And it seems that everyone they talk to has an opinion - waitresses, blues singers, and even a family friend who wants to give Dave a job to help support his new wife. Dave finally decides that he does love Karen enough to marry her, so he’s ready to go through with the proposal. But, in the back of his mind, he also hopes that she loves him enough to help him grow and to consider leaving the South Suburbs with him. Karen is surprised that Dave wants to change - surprised enough to rethink getting married. If Dave wants a fresh start with his life, it’s going to have to be a fresh start with Karen too.