Objective: Peer support is an essential component of adolescence and is instrumental in reducing feelings of isolation and loneliness. Yet, many youth and young adults experiencing a chronic medical condition conceal or minimize aspects of their conditions due to feared rejection. Disclosure practices in adolescents with chronic illnesses are not well-studied with little known about the nature of information disclosed. This study sought to better understand the relationship between the depth of information disclosed to friends and health-related quality of life, response to stress, and coping strategies. Methods: The sample consisted of 140 patients between the ages of 15–21 years who were recruited from seven sub-specialty medical clinics. Quantitative data was collected from a baseline survey examining disclosure, coping, and health-related quality of life. Results: Three groups were created and compared based on participant responses to the types of information being disclosed to friends: No Disclosure, Facts, and Concerns/Emotions. Participants who disclosed the psychological impact and concerns related to their condition tended to be female and had a significantly higher number of friends to whom they disclosed. This group of participants also tended to endorse higher levels of illness-related stress and was engaging in more positive coping strategies than those who chose not to disclose information or only shared objective information about their conditions. Conclusion: Understanding of the nuances of the depth and decision-making of disclosure is necessary for providers to be able to support youth with chronic illness as they navigate their social environment and relationships.