Work and masculinity are inextricably linked in post-war Japan. Although the employment system has changed in the last 20 years it appears that social attitudes of what men should do and be are changing at a slower pace. Men and women of varied ages continue to stress that men should be responsible breadwinners, husbands and fathers. Male freeters, many of whom are attempting to pursue and create alternative lifestyles, are often unable and unwilling to fill this normative role. This paper explores how male freeters negotiate dominant discourses of work, masculinity and maturity in their attempts to create alternative lifestyles whilst simultaneously expecting to fail. Furthermore, it argues for a deeper analysis of women’s effects on the construction of masculinities in Japan.