The lives of a group of young Chicago men, as seen through the eyes of one of them, a thirty-something writer suffering from the early onset of midlife crisis brought on by nostalgia, his dying friend and the wedding of his old flame.
A man and a woman go out on a "big" third date. He's ashamed to admit he just lost his job, and she's afraid he'll run away if he finds out that she has a kid. Small lies lead to bigger ones and the night gets crazy very soon.