In recent decades renewed attention has been given to the notion of middle age and particularly to women in this age group. Many of us think that this is a welcome development. These women (popularly referred to as “baby boomers”) have capitalized on the major sociocultural changes and transformed meanings and behavioral codes traditionally attached to this age group. In numerous interviews, in both academic and popular media, the dominant sentiment voiced by middleaged women is of overall satisfaction, to the effect that “the puzzle [life issues] straightens out … there is a greater sense of confidence in relations and overall a greater sense of authenticity … now it is totally me.” The discussion becomes complicated, however, when issues related to body image and, particularly, sex appeal are raised. Statements such as “I feel invisible … I don’t attract men” can be heard. It is as though there has been a trade-off: a sense of greater self-assertion in return for vulnerability vis-à-vis desirability and romance. Therefore, issues related to well-being and the quality of life of women in this age group cannot be easily measured. In this chapter I will discuss changes in gendered-age roles of women in this age group and the fragmented structure of well-being that results.