This research focuses on the complex meaning and role of the city in American and French rural gay men's imaginary and life experience. It explores how gay men who grew up in the country build their sense of self through back-and-forth movement from rural to urban spaces. Therefore, it questions traditional gay migration studies, which have often equated gay migration and rural-urban migration, positing a unidirectional pattern. After contextualizing rural male homosexuality, this paper presents four life itineraries which highlight the central role the city has for rural gay men when exploring their same-sex desires and attractions. Based on the analysis of their life narratives, we show that for most of them, their coming out, their first same-sex experience, and coming to terms with their sexuality happens "far from home" in a city or a college town. However, this research suggests that the city has a more ambivalent role for rural gay men. While the city exists as a space of social practices where alternative sexualities can be experienced and explored, at the same time for many rural gay men the city remains substantially unattractive. In their view, the perceived "effeminizing power" of the city questions and challenges their attraction for this space. Therefore, the experience of the city becomes both liberating and disciplinary--liberating because it allows the exploration of their same-sex desires and attractions, disciplinary because it (re)presents a gay identity in which they find no resonance. Thus this research indicates that rural gay migration to the urban spaces, which is key to identity formation, includes not only departure to the city but also a necessary return to the country to maintain rural gay men's understanding of themselves.