When we meet Bob Funk, he isn't much of a role model for the upwardly mobile Generation X or anyone for that matter - For starters, he is laudably outspoken, crass and seemingly reprehensible. With serious ex-wife and family issues, he has no idea how to be sober and human in his own skin. As a result, Bob has become acerbic yet irreverently charming with just about everybody he runs into.

To get through the day, Bob drinks exorbitantly, lives one 'one night stand' to the next, slacks through work, disobeys orders and is barely tolerated by those who know him. And he just doesn't give a damn.

Bob's life takes a turn however when an attractive young executive (Rachael Leigh Cook) joins the family company run by his mother, and becomes the object of his affection. Can the lovely Miss Thorne see past this cad to true love?