AbstractWe describe GuysWork, a school‐based healthy living program for adolescent boys, and share results from a pilot evaluation in Nova Scotia, Canada, during COVID‐19. The team hypothesized the program would reduce loneliness, perceived stress, and adherence to key traditional male gender role norms postprogram. A longitudinal cohort pre‐ and postsurvey design was used. One‐hundred fifty‐two participants completed sections of UCLA Loneliness Scale, Perceived Stress Scale, and the Meanings of Adolescent Male‐Role Norms Scale (MAMS). Results were nonsignificant for loneliness and perceived stress. MAMS results were statistically significant with a medium effect size (r = −.26) but there are limitations in the study. This pilot study of GuysWork has resulted in important lessons learned that will ensure a forthcoming Atlantic Canada‐wide evaluation results in robust evidence with the potential to support the need for masculinity norm‐changing work specifically for adolescent boys in schools.