At the age of four, Will Martin lost his parents and went to live with his grandparents. The warm memories of life in a small town and the old-fashioned Christmas holidays he and his grandparents shared sustain him still as a young man making his way in the world.

Years later, Will takes a leave of absence from his job in New York City to return home after his grandfather's death to help run the family real estate business. There he discovers something about his grandfather's past that shatters him and the memories of the life he so loved. At dinner one evening, his grandmother tells Will that she has been reading her husband's journals and learned that every Christmas Eve, when she and Will were out doing their traditional last-minute shopping, her husband was seeing a woman named Lillian. This year, his grandmother's Christmas wish is for Will to find out who Lillian is and why Will's grandfather, a seemingly devoted husband, saw Lillian every year for more than twenty-seven years and never mentioned her name.

As Will struggles to salvage the family business and learn the truth about Lillian, he approaches a revelation that teaches him a lesson in the power of kindness, forgiveness, and love to uplift an entire community and touch each life within it.