After Margaret complains that she and Sadie had a lacklustre summer, Sadie comes up with a "risk list" that will make their first days back at school a little more exciting. While Margaret breezes through the challenges, Sadie finds it increasingly difficult, especially when it comes to the final risk: asking Owen out. Her predicament is only made worse by the fact that she finds herself strangely attracted to the new kid in school - Ben Harrison. Meanwhile, Hal mentors Rain in the Tao of Hal, a "philosophy" that should help Rain get closer to his crush, Vivian.