This study aimed to explore adolescent boys’ views of masculinity and emotion management and their potential effects on well-being. Interviews with 33 adolescent boys aged 16 - €“17 years in Sweden were analysed using grounded theory. We found two main categories of masculine conceptions in adolescent boys: gender-normative masculinity with emphasis on group-based values, and non-gender-normative masculinity based on personal values. Gender-normative masculinity comprised two seemingly opposite emotional masculinity orientations, one towards toughness and the other towards sensitivity, both of which were highly influenced by contextual and situational group norms and demands, despite their expressions contrasting each other. Non-gender-normative masculinity included an orientation towards sincerity emphasising the personal values of the boys; emotions were expressed more independently of peer group norms. Our findings suggest that different masculinities and the expression of emotions are strongly intertwined and that managing emotions is vital for well-being.