Charles Whitley is a wealthy businessman living in 1903, but he feels unfulfilled with his life. One day, he meets a mysterious woman who gives him a pocket watch and tells him to "follow his heart." He later discovers that the pocket watch has magical powers and transports him to the year 2020.
In 2020, Charles meets Megan Turner, a tour guide at his historic mansion who is amazed by his appearance and believes him to be an actor hired for the Christmas tour. Charles is taken aback by the changes in society and the concept of Christmas, which he finds commercialized and devoid of its true meaning.
As Charles navigates this unfamiliar world, he grows closer to Megan and begins to question his own beliefs and values. Meanwhile, he must also try to find a way to return to his own time before it's too late.
Together, Charles and Megan explore 21st-century Christmas traditions, such as ice skating, caroling, and visiting Santa Claus. As they spend more time together, they develop feelings for each other, but Charles knows he will eventually have to return to his own time.
In the end, Charles discovers the true meaning of Christmas and finds a way to reconcile his past and present. He returns to his own time, but not before leaving a lasting impact on Megan and the people he met in the 21st century.