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Guided by both the social–cognitive model of career management and social comparison theory, this study compared men’s own well-being and their perceptions of other men’s well-being in the context of male gender norms and work–family management. Working men (N = 693) who adhere to traditional male gender norms reported lower levels of well-being. The same group of working men assessed other men who adhere to traditional male gender norms as having lower levels of well-being. Notably, men who adhered to traditional masculine norms were more likely to perceive that other men are “happier.” Further, “less happy” men (men in the low own well-being class) tended to rate other men “happier,” whereas “happier” men (men in the medium own well-being class) did not share that tendency. Lastly, men who reported higher levels of multiple role self-efficacy and positive work–family spillover reported that their own well-being was higher and reported that other men would have higher levels of well-being when they also have higher levels of multiple role self-efficacy and positive work–family spillover. These findings are discussed within the context of the social comparison and work–family interface literature. Implications for future research and practice also are addressed.