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. Kylie and Whitt clash at first, and it looks like Whitt will never be able to help her if he doesn't understand her situation. But when Kylie and her son's future as a family is suddenly threatened, Whitt discovers he and Kylie may not be so different, after all.