Darlington Industries is a successful family business; the Darlingtons an old-money family in Connecticut. After 2 1/2 years in the position, in the New Year Jessica Lew is moving up from efficient, trusted Executive Assistant to company CEO Charles Darlington to working int he company’s legal division, as she has just passed the bar exam and earned her law degree. As Charles is scheduled to head off to Europe for a business trip, he asks Jess to do one last task before her much-deserved Christmas break: pick up Charles’ orphaned nieces and nephew—Emma, Abby, and J. Henry—from the airport; they’re coming “home” after spending four years in Australia. Their father was Charles’ engineer brother Jarrett. Legal arrangements have been made for Charles and the third brother, Max, to assume custody of the three children. Max is considered the wild, irresponsible one who, despite officially being the company President, has no dealings with the company as he carries on with his carefree life doing what he pleases. With Charles away, Max not even aware of this new situation, and their aging longtime housekeeper Mrs. Brooks unable to care for three children on her own, Charles has arranged for the children to spend Christmas at the boarding school they will attend in the new year. Individually, Jess—not wanting the children to be alone on Christmas, understanding such a situation too well—and Max upon learning of the children now being under his and Charles’ care; decide to forgo their Christmas plans to spend Christmas at Darlington Manor with the children. During this time, Jess not only discovers how sweet the children are, but also that Max, whom she hasn’t dealt with much, is a better, more-substantial person than he seems—Charles doesn’t give him enough credit or actually see the real Max. Jess and Max start to fall for each other and envision a different path for themselves and the children—if only Charles, who is actually in charge of the children, can reshape his view of his younger brother.