“How have you gotten out of your comfort zone?” That’s the Stanford University essay prompt keeping senior Aisha Agarwal up at night. As a daughter of immigrant parents, and a shoo-in for valedictorian, Aisha’s straight-and-narrow path has always guaranteed safety and success. But after her longtime crush, fellow brain Brian, stands her up at winter formal, Aisha decides that playing it safe just isn’t worth it anymore. As if on cue, a banged-up Volkswagen arrives at the dance. Soon Aisha is unloading all to her would-be chauffeur, seventeen-year-old Quentin. To her surprise, her easygoing confidante opens up too, leading to a deal: if Aisha helps Quentin pass math, he’ll help push her out of her comfort zone, using a series of sticky note to-dos—dares—that will not only give Aisha something to write about for her Stanford essay, but will create a version of herself that Brian can’t resist.