Little is known about the family setting and the role of family education in a setting where "intimacy and justice are intertwined" (Okin, 1989). Most intriguing is the unique moral and complex relationship between mother-in-law and daughter-in-law: what is the nature of these two women's failure to maintain harmony between themselves even though the literature suggests that they are predominantly care-orientated? The following paper questions whether there is a problematic relationship between Israeli mothers-in-law and their daughters-in-law. It further attempts to examine whether there is an association between selected situational variables (work outside the home, years of marriage), personality variables (moral orientation, depressive mood and general life satisfaction) and the quality of the relationship between mothers-in-law and daughters-in-law. It seems that being cast in the role of the mother-in-law most probably overrides any other situational or personality variable. It created an ongoing asymmetry between the psychological experience of the mothers-in-law and the daughters-in-law, which is being discussed.