To optimally address sex and sexuality, normalize gender and sexual diversities, and attend to adolescents’ needs, clinicians will best serve their patients and their families by becoming comfortable initiating confidential, developmentally appropriate discussions with all adolescent patients. The goal is to create a safe, affirming, nonjudgmental space wherein adolescents may learn about sexual matters, discuss concerns, ask questions, and find support to assist them to achieve healthy, positive development. This article provides useful, practical suggestions to begin these conversations, offers specific examples and tips to encourage dialogue, and discusses ways to be a resource to adolescent patients.