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?
Mom has had it and it isn't long before Bob is fired from his lofty executive position for his sexist and politically incorrect behavior toward the lovely new executive. To add insult to injury, his mother insists that the only way he can regain his job is if Bob sees a female psychiatrist, reports to a female boss (Ms. Thorne) and quits drinking. If he agrees to these terms, he can stay in the family business - as the office janitor.
The series of career and personal setbacks brought on by his own hubris puts Bob's life into perspective and slowly, Bob begins to realize there is more to life than sex and booze. Eventually, he becomes motivated to straighten his life out once and for all. But this is Bob Funk. Can he actually make friends, be polite and treat women with respect -- all while remaining sober and holding down a steady job? With Bob Funk, anything is possible, even true love!