Evolutionary theories of human attraction draw heavily upon nonhuman literature, and currently the Immunocompetence Handicap Hypothesis dominates research into female attraction to male facial masculinity. Although some studies have shown links between masculinity and some measures of health, other data have failed to support the Immunocompetence Hypothesis as applied to human face preferences. Here we summarize that literature and present new data regarding links between masculinity and multiple measures of health condition in human males. Undergraduate males were photographed and their faces were assessed for sexual dimorphism using multiple methods and rated for apparent healthiness and attractiveness. Participants also reported recent health experiences both prior to being photographed and then again 10 weeks later. Although both attractiveness and rated health were associated with better actual health in the past and future (mainly indexed by lower antibiotic use), results were mixed for masculinity. With respect to respiratory illnesses, facial masculinity (assessed using morphometric techniques) was associated with better past health but with worse future health. Possible reasons for the complex and inconsistent findings are discussed and some potentially fruitful avenues of future research are outlined.