Background The period of adolescence can be a challenging time for boys, particularly in forming their own self‐identity and reputation. In the school context, boys can often adopt a “tough” masculine image (e.g., alpha male) out of fear of being coined weak or being seen as inferior among their peer group. Thus, for an adolescent boy to adopt a compassionate self‐identity at school is a risk to his reputation because to be compassionate can also be viewed as being weak by one's peer group. Yet both of these views of “weak” are misconceptions of what it means to be masculine and compassionate. Method This article examines masculinity and compassion through an evolutionary perspective, with an aim to demonstrate how compassion can help adolescent boys with hegemonic masculine identities. Results This article focuses on the following areas in understanding masculinity and compassion in boys: (1) evolutionary and biological approaches to masculinity and compassion, (2) adolescence and reputations, (3) the role of environment, (4) interventions, and (5) a series of recommendations for future research exploring links between compassion and masculinity. Conclusion Collectively, this article proposes that masculinity and compassion need to be understood in terms of evolutionary models to help better understand how these constructs function and what factors facilitate and inhibit them.