Reaching beyond the media portrayals of 'dangerous migrant men', we ask what bachelorhood entails for migrated men within the European union. Using ethnographic data from Italy and interviews from Sweden, and drawing on previous research, we suggest that critical masculinity studies can be combined with the transnational family framework to situate the single men in a relational and transnational context. Our results indicate that bachelorhood is experienced as both freedom and a challenge to build a life that stretches across cultures and nationalities. In this context, masculinity is construed as both freedom from relations and as (conflicting) loyalties. Considering some differences between Italy and Sweden, we suggest ways in which to further examine transnational bachelorhood across Europe and across groups of migrating men.