After ending her engagement, thirty-something Andi Cutrone leaves New England and returns to her hometown of Long Island to put the past behind her and focus on her career. When she meets Devin at a cocktail party, she is both shocked and fascinated. He is a genuine playboy. A few months later, she spontaneously calls him. During a cheesecake date at a café in Brooklyn, she makes him an offer: he should teach her how to be better in bed, and in return, she will pay him with writing lessons. To Andi's surprise, Devin agrees. An intense relationship develops between them, one that is as educational as it is exhilarating. Through lessons in writing theories and foreplay techniques, Andi and Devin unexpectedly delve into the big questions of truth, beauty, and identity.