Purpose: This study investigated the effects of gender differences on the association of chronic stress and depressive symptoms in middle-aged and older adults in Taiwan. Methods: The population base was of adults aged 50 and older in Taiwan. This study included 2,889 participants and examined the gender differences on the impacts of life stress that exhibited depressive symptoms. Results: Females were more susceptible to depressive symptoms when they felt constant stress from finances, increasing stress from jobs, and fluctuating stress from family relationships. Discussion: Gender differences were evident when assuming social roles, as were psychological susceptibilities.