Objectives: The primary purpose of this study is to investigate the relationship between middle-aged men’s self-differentiation, chemyon (face) sensitivity, and family communication. Methods: A quantitative survey was conducted with 269 men aged 40 to 59. Results: The research findings are as follows: first, analysis considering factors related to middle-aged men’s basic characteristics indicates considerable differences in their respective religions. Second, the correlation analysis shows that there is a meaningful relation between family communication, self-differentiation, and chemyon (face) sensitivity. Third, the result of multiple regression analysis investigating factors that affect middle-aged men’s family communication shows that it is heavily related to religion (one of the basic characteristics), self-differentiation, and chemyon (face) sensitivity. Conclusions: The findings of this research not only support the improved quality of life and healthy lifestyle for middle-aged men, but also function as the basic data for family therapy and family counseling, as required for arranging their system.