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.

As a little girl, Melanie Hogan wished to find her own prince charming just like her parents found true love. Now an adult, Melanie is running her own bakery and dating a handsome CEO, Justin. Although things seem perfect when Justin asks Melanie to spend the holidays together at his beautiful lake house upstate—and meet his mother. Melanie finds herself spending more time with Justin’s best friend and loyal assistant, Dean, who just might be harboring a secret crush on her. When complications arise that throw Melanie and Dean together over the holiday, will the two realize they're meant to be?

When a temperamental Broadway director is fired from yet another job, she is forced to direct a community Christmas pageant.