There is a need to expand the current focus of burnout in medical trainees so that we can understand not only trainee distress but also trainee well-being. Work engagement as measured by the Utrecht Work Engagement Scale-15 (UWES-15) is a positive construct that is conceptually related to burnout and is a component of the Job Demands-Resources Model (JD-R). We sought to explore the relationship of work engagement to burnout, perceived stress, lifestyle factors, and medical student attitudes to testing whether work engagement could serve as a positive construct to study medical student well-being. We surveyed 287 1st and 2nd-year medical students at a large academic medical center in the United States. Our survey consisted of demographic measures, UWES-15, Burnout Measure short version, Perceived Stress Scale-4, lifestyle factors, and medical student attitudes. Statistical analysis revealed work engagement is negatively correlated with burnout and perceived stress. Work engagement and its subscales are correlated to exercise, sleep, drugs and alcohol use, maintaining relationships, and financial stress. Work engagement is negatively correlated with thoughts of dropping out and questioning the decision to enter medical school. Work engagement can be a useful measure to assess medical student well-being and identify areas for intervention.