Preppy and wealthy Whitt Sheffield is in his last semester of law school when a professor assigns him to act as an advocate for a young, single mother who needs help finding - and keeping - a job. Whitt (Justin Bruening), whose snooty father wants Whitt to follow him into corporate law, is insulted by the low-class assignment, especially after he meets Kylie Burch (Jodi Lyn O’Keefe), the woman he has to help.