Adolescence should be a time of healthy growth and development. Indeed, it is a critical period with significant physical, emotional, and mental changes. Despite robust physical health, adolescent risky behaviors may result in lifelong consequences as well as increased morbidity and mortality. The HEEADSSS review of systems is a tool to understand adolescent behavior and assess risk-taking behaviors to provide appropriate interventions. Using the HEEADSSS review of systems is an effective way to engage in dialogue with teens and address many of the challenges faced by this age group.