Preppy and wealthy Whitt Sheffield (Justin Bruening) is in his last semester of law school at Morgan College when his radical-thinking professor, Victoria Corrales (Constance Marie), gives his class a very different kind of assignment: to act as a mentor and advocate for a young, single mother who needs help finding-and keeping-a job. Whitt, whose snooty father, Benjamin (Eric Roberts), 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. Given their extreme opposite backgrounds, 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.
Then, Kylie's seven-year-old son, Shane (Maxwell Perry Cotton), gets very sick and must be rushed to the emergency room. Seeing how desperate Kylie needs a job to be able to care for her son, Whitt begins spending more time with her. As Whitt becomes more attracted to Kylie and bonds with Shane, his family and friends question Whitt's movement out of his social circle. Then, when Shane and Kylie's future as a family is suddenly threatened, Whitt discovers he and Kylie may not be so different, after all.