The adaptation to a new country is a complex and stressful process that is compounded when changes in status and identity have to be made. This exploratory study examined the adaptation of international company transferee spouses when they decide to follow the transferee on overseas assignments. Research to date indicates that the spouses’ dissatisfaction with life abroad is the leading cause of transferees breaking contract and prematurely returning home. The causes of this dissatisfaction are still not clear and this study sought greater clarification, particularly examining the experiences of male as well as female trailing spouses. The study, thus, takes gender as a main variable to consider. It explores how gendered expectations inherent in the structures of society inflect and inform the decisions, attitudes, and behaviors that affect the adaptations of trailing spouses living in a foreign habitus. The study is based on eight months of ethnographic research in two culturally different locations, Kuala Lumpur, Malaysia and Brussels, Belgium. Forty-two American international company transferee spouses were recruited (seven males and thirty-five females). The data analysis revolved around five main themes: (1) the comparison of male with female trailing spouses’ experiences, (2) the effect of location on spouses’ adaptation, (3) the communities that spouses integrate into, (4) variations in personal work and family histories, and (5) conditions of exit. The analysis engaged multiple theories regarding gender, sociological adaptation, and psychological adaptation. Results indicate that both socio-cultural and psychological factors affect adaptation and that gender matters very significantly, particularly along two axes: (1) gendered structures in our society create different reasons why males and females become trailing spouses, (2) the gendered social constructions of role expectations make the experience of being a trailing husband different from being a trailing wife. In addition spouses’ status as parents (or not) and their “readiness for change” were found to be important predictors of positive spousal adaptation. In contrast, significant ties with families in the home country and strong professional identity with career projections were important predictors of negative spousal adaptation.