The purpose of this study was to assess the relationship between masculine gender role conflict, attachment variables, narcissism, and adjustment. It was expected that men who reported higher masculine gender role conflict would also report unhealthy attachment, have a greater degree of narcissism and poorer adjustment. This study employed a sample of undergraduate males who completed self-report questionnaires measuring masculine gender role conflict, narcissism, adjustment, and attachment. Hypotheses were tested using canonical correlation techniques. Results indicated that healthy attachment was related to low masculine gender role conflict; however, unhealthy attachment was not related to high masculine gender role conflict. In terms of narcissism, higher amounts of narcissism were related to high amounts of gender role conflict, but in a subset of results individuals who reported low masculine gender role conflict also reported higher narcissism in areas that are assumed to relate to positive self regard. Results related to adjustment indicated that high masculine gender role conflict was related to less psychological well-being replicating past studies. Theoretical and methodological issues were discussed in light of these findings.