Contemporary screenwriter Lucy Hardgrove is hired to pen the remake of the holiday classic His Merry Wife!, which was shot at the renowned Biltmore Estate. Taking a tour of the grounds, she accidentally knocks over an hourglass, transporting her back in time to 1946, right when His Merry Wife! is being filmed.

In 1951, a doctor wants to make the holiday special for his worried wife before he is shipped out to serve in Korea, but when she suffers a minor fracture to her arm his carefully planned out Christmas Eve plans are upended. In 2003, a newly married couple who are always in agreement about everything hosts two sets of in-laws for Christmas Eve for the first time and find that they may not have had as much in common as they thought they did. And in 2024, a couple tries to arrange special Christmas surprises for each other but keeping them a secret may be harder than they thought.