This study examined the relationships between stressful life events in childhood and differentiation of self and intergenerational triangulation in adulthood. The sample included 217 students (173 females and 44 males) from a college in northern Israel. Participants completed the Hebrew versions of Life Events Checklist (LEC), Differentiation of Self Inventory-Revised (DSI-R) and intergenerational triangulation (INTRI). The main findings were that levels of stressful life events during childhood and adolescence among both genders were positively correlated with the levels of fusion with others and intergenerational triangulation. The levels of positive life events were negatively related to levels of emotional reactivity, emotional cut-off and intergenerational triangulation. Levels of stressful life events in females were positively correlated with emotional reactivity. Intergenerational triangulation was correlated with emotional reactivity, emotional cut-off, fusion with others and I-position. Findings suggest that families that experience higher levels of stressful life events may be at risk for higher levels of intergenerational triangulation and lower levels of differentiation of self.