Background: Outpatient clinic visits are a window of opportunity to address health risk behaviors and promote a healthier lifestyle among young people. The HEADS (Home, Education, Eating, Activities, Drugs [i.e. substance use including tobacco, alcohol, and illegal drugs], Sexuality [including contraception], Safety, Self-harm) interview is a feasible way of exploring health risk behaviors and resilience. Objective: The purpose of this study was to evaluate how often HEADS topics were addressed according to young patients and staff in pediatric and adult outpatient clinics. Methods: We conducted a questionnaire survey among young patients and health care professionals at a tertiary university hospital. Young patients reported on their cumulative experience and staff reported on their usual practice. Results: A total of 290 young patients aged 12–22 years (78% having a chronic condition) and 97 health care professionals participated. We found only small reported differences between staff and young patients regarding whether home, education, and activity were addressed. However, staff reported twice the rate of addressing smoking, alcohol, illegal drugs, sexuality, and contraception compared to young patients. Young patients reported that smoking, alcohol, illegal drugs, sexuality, and contraception were addressed significantly more at adult clinics in comparison to pediatric clinics. After controlling for age, gender and duration of illness, according to young patients, adjusted odds ratios for addressing smoking at adult vs. pediatric clinics was 2.47 (95% confidence interval [CI]: 1.26–4.83), alcohol 2.84 (95% CI:1.45–5.57), illegal drugs 4.20 (95% CI:1.69–10.44), sexuality 3.54 (95% CI: 1.67–7.50), contraception 3.68 (95% CI:1.61–8.41), and any of the above 2.95 (95% CI: 1.47–5.91). Conclusion: According to young patients, smoking, alcohol, illegal drugs, sexuality, and contraception were not routinely addressed at a tertiary hospital, and especially at paediatric clinics, these issues were seldom addressed.