Lily (Midori Francis), who loves Christmas, decides to start something fun. She places a red notebook with the title "Do You Dare?" on the shelf of her favorite book store in New York City, in between other books. Dash (Austin Abrams) comes along and finds the notebook. Intrigued, he opens it to find a question asking how this time of year makes him feel. A true cynic, he writes that he hates Christmas, calling it "the most detestable time of the year."
Disappointed, she leaves another message for Dash, assigning him a dare, which if completed, will give him a clue to her identity. He completes the task and assigns her a dare of her own.
They continue to pass notes back and forth and decide they'd like to meet, but Lily worries that she won't measure up to the girl he may be expecting. Undaunted, Dash goes on a quest to find her.