James and Lindsay both grew up in Madison, Connecticut and attended Ryerson Elementary School together. They first met in the second grade and quickly became friends (although James fails to remember this detail). James and Lindsay attended public school in Madison until they left for college. Years later, they met again at a local brewery and quickly fell in love. Even on their first date, Lindsay knew James was the one she wanted to spend the rest of her life with. Three years later, on December 23, 2021 (20 years from the second grade) James proposed.