We 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 = -0.26) 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.