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Research has consistently found that expressing emotion related to distressing events promotes social adjustment (Rimé, 2007, 2009), whereas suppression of negative emotion has social costs (e.g., Gross & John, 2003). However, prior research has largely failed to take into account the degree of relationship between the distressed individual and the person to whom the distressed individual is speaking, and the social norms of the population to which the distressed individual belongs. Considering these factors, the relationship between emotional expressivity and social adjustment may be more complicated than the emotional regulation literature would suggest. Thus, the primary aim of this study was to examine the relationship between social adjustment and emotional expressivity toward friends and nonfriends in a sample of late adolescent males, through the lens of masculinity research that suggests that low emotional expressivity may be adaptive for males in certain contexts. Adolescent boys (N = 178) reported the degree to which they expressed emotion to friends and to nonfriends (which includes acquaintances and strangers). Results indicated that for these boys, emotional expressivity was associated with better social adjustment only when the expression of emotion occurred within the context of friendship. Additionally, boys who exhibited greater “expressive flexibility,” expressing more to friends than nonfriends, reported the greatest social adjustment.