As 34-year-old Timothy Dugan makes his way through life, he is beset by a growing list of problems.

His girlfriend, a full-time college student, wants to have a baby, he hates his job, and his mother announces that she and his father, long divorced, plan to remarry. He copes by drinking too much. When his mother suggests it's time for another round of therapy, Timothy loudly resists. He knows his outlook is sour and vows to do better. Then Harcourt, a former fraternity brother, presents him with an attractive business opportunity to get in on a home-building business, and things start to look up. Timothy happily resigns his position as manager of the local GAP store. Harcourt, however, has a bad habit of cutting corners to save money and things fall apart. Timothy feels the best way to get his feet back under him is to nail things down with Sam, so he buys her an insanely expensive engagement ring she says is all wrong. She comes around to the idea of marriage after meeting Melissa, Timothy's former girlfriend, who has a son Timothy didn't know about. Timothy's feelings are stirred up by Melissa's presence, and he goes into a slow-motion train wreck. Promise after promise is broken until Sam reaches a breaking point. She's committed to Timothy, but their future is dark. Will her love light the way again? Or has she finally had enough?