Sixteen-year-old Lily left a red notebook full of challenges on her favorite bookstore shelf, waiting for just the right guy to come along and accept is dares. Dash, in a bad mood during the holidays, happens to be the first guy to find the notebook and rise to its challenges. What follows is a whirlwind romance as the two trade dares, dreams, and desires in the notebook they pass back and forth a locations 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?