Emerging adulthood is a transitional time often marked by instability in many areas of life, including residential status, work, school, and romantic relationships. The purpose of this study is to examine transitions in HIV-risk related behaviors among a cohort of ethnically-diverse young men who have sex with men (YMSM) and to reveal how changes in developmental contexts during emerging adulthood might be associated with these behavioral changes. Hidden Markov models were used to examine movement across different stages of behavioral risk-taking over time. Semi-annual surveys were administered across 2 years; analyses included those with at least three of the five waves of data. Results indicated substantial movement at the individual-level transitions. Additionally, high variability in sexual risk, alcohol misuse, and illicit drug-risk behaviors was predicted by age, ethnicity, and correlates of emerging adulthood, such as residential status, work, post-secondary school enrollment, and primary-relationship status. Findings provide evidence of great change in risky behaviors among YMSM during this pivotal time, particularly among those who actively experiment in varying levels of risk-taking. In order to prevent experimental behaviors from evolving into more serious risk, interventions must consider ways to assist YMSM to adjust to life changes brought on by emerging adulthood.