This article tries to find out whether “the glass ceiling” concept, coined and used to describe the woman’s status, is also applicable to men. Gender theory and empirical research based on this theory will help us to realize this objective. Analysis of empirical data covering a brief period (1998–2002) within the transformation process allowed us to formulate an intriguing yet optimistic conclusion as far asmen are concerned. If the hypothetical identification of the male “glass ceiling” with an unfortunate pattern of sex-typing is confirmed, we will be able to say that the men’s situation is paradoxically rather good. The presented results show that the changes in gender self-definition whichmen have undergone in so short a time and which have led to a shift from the former dominant poor gender definition to cultural masculinity, and the simultaneous enrichment of this self-definition with traits conducive to relation building (“caring,” “emotional,” “affectionate”), place men in the position of individuals who are more social adapted than before. Our sociological diagnosis suggests that the proportion of culturally androgynous men may increase in Poland.