Phoebe recalls her childhood obsession with falling in love, fueled by devouring romance novels. Despite her romantic longing, by seventh grade, she was the only one of her friends who had not had her first kiss. At a welcome-back assembly, her friends conspired to sit Phoebe next to her crush, Lucas Johnson. As Lucas put his arm around her, Phoebe was overcome by a sudden panic attack. As Lucas leaned in to kiss her, Phoebe projectile vomited all over him. The incident reinforced her belief that something was fundamentally wrong with her and shaped a lasting pattern of avoidance around physical intimacy. Now, 17 years later, she’s still a virgin and about to turn 30.

On a Monday, 30 days before her 30th birthday, Phoebe has a session with her therapist, Sandy. Phoebe feels distraught over a letter she wrote to herself at age 18 for a school assignment in which students were asked to set goals to achieve by the time they turned 30. The teacher promised to mail all the students their letters just before their milestone birthdays, and Phoebe’s has just arrived in the mail. In her letter Phoebe wrote a single goal: “Lose your virginity.