Scholars have addressed the economic, gendered, and emotional dimensions of migration, especially as migrants move from origin to destination. However, scholarship on return migration and the subjective experiences of reintegrating to origin communities is poorly understood. In this paper, we examine the return migration of formerly unauthorized migrants who labored as roofers in the United States. We argue that the migration process redefines men’s masculinity as they attempt to balance family life in Mexico and their occupational lives in the U.S., all of which are essential for their identity but remain separated by an international border. We draw on 40 in-depth interviews with return migrant men in a small city in Guanajuato, Mexico to examine the emotional tensions men experience regarding the decision to remain in close proximity to family in Mexico and a desire to return again to their economically and emotionally fulfilling occupations in the U.S. We find that migrants’ nostalgia for prior U.S. labor market experience, in juxtaposition to reentry into the Mexican labor market, competes with current feelings of happiness and contentment obtained through family reintegration. These competing feelings, together with economic need, help explain the complex meaning of migration for return migrant men. We conclude by suggesting that once men have been exposed to U.S. life, the occupational identity becomes a “pull” that encourages future migration trips.