Jack (Andrew McCarthy) is an executive in a financial brokerage firm trying to impress the firm’s president, Drew Clayton (Chris Gillett), in hopes of a promotion. However, Jack is dating the fabulously rich and elegant Demi Clayton (Stephanie Mills), who happens to be Drew’s daughter. Although Demi’s mother Clarisse (Jane Moffat) doesn’t necessarily approve of Jack and would prefer her daughter to date a man within their social circle, Jack still plans on proposing. Trying to create the perfect proposal, Jack signs up for dance lessons in preparation for his proposal to Demi at her father’s lavish annual Christmas Dance. But when sparks start to fly between Jack and his dance instructor, Christine (Michelle Nolden), Jack will have to make some important decisions before it is too late.
Chicago native Emily Jones (Autumn Reeser) loves her city, and has dedicated her career to coordinating its beloved Thanksgiving Day parade every year. This year, Emily is hoping for a memorable holiday and anticipating a long-awaited proposal from her long-distance boyfriend Brian (Ben Cotton). Then, the parade director hires a wealthy development consultant, Henry Williams (Antonio Cupo), to analyze the finances of the parade and increase profits.
Dr. Lauren Brunell (Bure) has her whole life planned out. As a third year surgery resident, she is counting on being accepted into a prestigious hospital fellowship to follow in the footsteps of her supportive father, Henry (Pine). But when those plans quickly fall apart, and Lauren is put on the wait list, she must take the only other opening available: a head doctor position in the small, remote town of Garland, Alaska. Convincing herself it is only temporary, Lauren moves to Garland where she is immediately charmed by Andy (O’Donnell), a handsome local who soon starts to show her the importance of living in the moment and enjoying her unexpected adventure. As Lauren excels as Garland's trusted doctor, she warms up to the friendly town. But Andy's father, Frank (Doyle-Murray), is hiding something from her in his top-secret shipping warehouse. Just as Lauren decides to get to the bottom of her suspicions, she receives news that will force her to make a life-changing decision, while knowing for certain that the Christmas season will never be the same.
