New York based jazz pianist Willie Conway heads back to his small hometown of Knights Ridge, Massachusetts for a high school reunion. The trip is as much to go to the reunion and see his old friends - none of whom left Knights Ridge after graduation - as it is to get away from his current life, at which he is at a crossroads both personally and professionally. He is just eking out a living with his piano playing gigs, and as such he is thinking about taking a sales job. He's also not sure if he's ready to marry his long time girlfriend, lawyer Tracy Stover. Most of Willie's Knights Ridge blue collar friends' best days were in high school, they still having that "trophy" mentality of girlfriends and wives. Only Michael "Mo" Morris is happily married with a family. Paul Kirkwood, whose room is plastered with magazine pictures of models, wants his waitress ex-girlfriend Jan back only because he knows now that he can't have her...