16-year-old Lily has left a red notebook full of challenges on her favorite bookstore shelf, waiting for just the right guy to come along and accept its dares. Dash, in a bad mood during the holidays, happens to be the first guy to pick up the notebook and rise to its challenges. What follows is a whirlwind romance as Dash and Lily trade dares, dreams, and desires in the notebook they pass back and forth at locations all across New York City. But can their in-person selves possibly connect as well as their notebook versions, or will their scavenger hunt end in a comic mismatch of disastrous proportions?