One of the first scenes shot was the romantic kissing scene by the fire between Jesse Tuck (Jonathan Jackson) and Winnie Foster (Alexis Bledel). Jackson, cast at the last minute, had not even met Bledel before shooting the scene.
Jonathan Jackson, playing a seventeen-year-old character, is one year younger than Alexis Bledel, who played a fifteen-year-old character. Bledel was twenty-one when this movie was released, and Jackson was twenty.
Actor Jared Padalecki was offered the role of Jesse Tuck due to his and Alexis Bledel's on-screen chemistry in Gilmore Girls (2000). However, Padalecki declined because he wanted to work with other people.