Objective of Study: Expatriate spouses have received increasing attention in empirical studies on expatriation and adjustment. Often these studies were conducted through a human resource management lens with samples that were mostly female. Drawing on gender role theory, masculine coping schema, and known phenomena of intercultural adjustment, my study researched the lived experience of male spouses of expatriate workers. I used a social work lens to explore male role and identity paradigms as constructed through cultural and social upbringing, and how those paradigms impact a man’s transition to a “trailing spouse” who is influenced by expatriate work culture and host country culture. Methods and Results: This was a phenomenological qualitative research study. The sample consisted of male spouses of expatriates who were working overseas through U.S. Diplomatic missions. I used a purposive, non-probability snowball sampling technique to recruit ten American men from nine different countries. These participants provided me with qualitative data during single-session interviews conducted over Zoom. I analyzed the data using a concept-driven thematic coding process with a combination of deductive and inductive analytical methods. I organized my results into five major themes and 18 subcategories. My major themes are: Perceiving oneself as a male expatriate spouse; Evaluating gender-based identity and roles; Negotiating culture; Adjusting to a process; and Cultivating a lifestyle. Conclusions: Most participants in this sample made a pre-determined choice to live the expatriate lifestyle; they did not “trail” or “follow” their wives overseas in a submissive sense, but instead were achieving the goal of expatriation in tandem with their spouses. These men were comfortable in their roles supporting their breadwinner spouses who were pursuing their careers abroad. Most participants created their own metrics for success and constructed a modern form of masculinity based on personal adaptability, which allowed them to feel comfortable in their roles. Participants were largely uninfluenced by host country cultures or their spouses’ organizational cultures, found connection with the expatriate cultures they interfaced with, and expressed some conflict in resolving the traditionally masculine elements of their home country cultures. Half of my participants maintained a desire to pursue their chosen careers and considered that to be a significant part of their identities. Implications: This study allows for a better understanding of how male expatriate spouses perceive their worlds, which can inform proactive and reactive mechanisms to support this population. Future studies should thoroughly explore the particular needs of male spouses of expatriates through the lenses of gender, culture, and work.