Men volunteering to mentor other men is a growing form of social engagement in Australia. Masculine norms associated with not disclosing emotional distress or discussing loneliness are often set aside by participating in these one‐to‐one relationships. Mentors have reported improvement in their well‐being and a desire to contribute more. In this phenomenological study, which draws on hermeneutic methodology, 12 men who voluntarily met and mentored another adult man for a minimum of 6 months participated in a semi‐structured interview. Findings showed non‐judgement and deep listening facilitated a rewarding and personally developmental relationship. Most voluntary mentors experienced substantial changes in their masculine views, particularly with the regard to trust and openness with others. This experience has implications for men realising their ability to engage others and for community well‐being.