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.

Bryce is ready to propose to Madison while they visit her family for Christmas. However, the spontaneous wedding of Madison's sister Harper throws Bryce's perfect proposal plans into a tailspin.