This article reviews the literature on masculinity and marriages, focusing on Thai women-farang (Caucasian) men marriages and how these relationships have been conceptualised. The review highlights the shift from emphasising the political, economic and international-relations dimensions that determine marriages to agency analysis, in which individual choices are informed by local and Western cultures/norms, global opportunities and local constraints. While studies have focused on women and their agency, men’s experiences are only beginning to emerge in recent scholarship, indicating both the negotiation and vulnerability of farang men coming from a more advantageous position. Studies of Thai-farang marriages have often centred on the presence of American troops in Thailand during the Vietnam War (1965–1975), while ignoring those that date back centuries. I posit that the history of transnational marriage should be considered in terms of changing structural conditions and that the balance between structural- and agency-centred explanations must be recognised.