This dissertation finds that where gay identity is seen as a foreign artifice or as a non-indigenous product of human evolution, gay migrant men are often forced to adjust gay identity for cultural “fit,” which requires spatial (re)placing and cross-cultural improvisation through the transnational imagination. This causes some gay men to reconstitute gay identity along spatial and cultural lines beyond their own sexual orientations and desires. This dissertation provides an original contribution to the study of sexual migration scholarship and is the first to explore the sexual identity changes of openly gay US men who migrate to South Korea. It adds to the growing narrative on gay identity in East Asia, while bringing to the fore the paradox of addressing sexual minority issues as a human rights concern rather than as a matter of sexual citizenship in the country. I use sociological methodologies and draw on the narrative accounts of openly gay US ex-patriots who migrated to Seoul from the late-90s to investigate how these men adjust to Korea's social conditions. Embedding my analysis in my informant’s transnational imagination of Korea culturally and socially, I also find that these men must relearn heteronormative expectations and masculinity, which greatly impact their being and belonging. Consequently, some begin to see gay identity as syncretic. They carefully mitigate their sexual behaviors to avoid risks, while relying on Korean role models and imitation. Others internalize gay identity as country-specific or culturally specific and see it in Korea as (1) antithetical to Korean values of filial piety and good citizenship; (2) a social liability; and (3) dangerous to their wellbeing in the country. These men re-constitute gay identity aimed at conformity and social inclusion. They adopt alternative sexual identities and even embrace alternative sexual desires. Viewed together, both groups adjust in Korea by finding sexual freedom in zones of flexible masculinity and in homes, both of which serve as crucial sites for sexual normalization. As a seldom studied group in the country, US gay men face multilayered forms of discrimination—from both Koreans in general and gay Koreans—as racialized/ethnic foreigners and as gay men. Using the transnational imagination, they employ tactics to win nominal membership and acceptance from native Koreans, while gaying or concealing their gay identities. As gay and foreign, these men are regulated to semi-welcomed status in the country. They also share similar fears of outing which could jeopardize the few in-group associations they have established in the country. The findings suggest that, contrary to expectations based on Becker’s labelling theory of sociology, a gay foreign enclave fails to manifest in the country.