(1) Background: The present study is aimed to determine the predicting role of objective (lifestyle) and subjective factors of middle-aged women's psycho-emotional health such as their relations with parents, attachment and separation types. Women who are overloaded with professional and family roles have high stress level, their indicators of psychological well-being and emotional level decrease when they have to give everyday care to their elderly parents. (2) Methods: The research sample has two empirical groups. Sample of Study 1 includes middle-aged women (n = 61) aged 38-56 (M = 48.1, SD = 3.5); sample of Study 2 includes middle-aged women (n = 85) aged 33-52 (M = 40.6, SD = 3.1): married (70.5%) and divorced (29.5%), having children of 14-28 years old; giving everyday care to elderly parents for more than 1.5 yrs. Some live separately (62.3 %), or have to cohabitate with parents (37.7%). All women evaluate their life situation as difficult and manifest signs of high psycho-emotional stress. We used methods adapted for the Russian-speaking sample: getting socio-demographic information, an interview; The scales of psychological well-being; Attachment style and Interpersonal Guilt Questionnaires (study 1); Psychological Separation Inventory, Purpose-in-Life Test, projective methods (study 2), mathematical statistics. (3) Results: A number of factors and indicators of women's psycho-emotional health decrease in the situation of role overload have been identified. Among the factors there are four main types of women's relationships with parents: Anxious closeness; Ambivalence of feelings; Secondary relationship with parents; Alienation, predicting of psycho-emotional health that are reducing or enhancing their personal resources. Besides, a type of separation of an adult woman from her mother predicts her level of well-being. (4) Conclusions: The study confirms that middle-aged Russian women's psycho-emotional health depends on contextual factors (difficult role-overloaded lifestyle) and factors integrating women's relations towards parents, attachment, guilt and separation. Types of middle-aged women's relationships with parents contribute to their psychoemotional health in a different way.