Since 1999 Colombia has experienced dramatic increases in emigration, particularly the emigration of women towards the U.S. as fiancées of U.S. citizens or residents. Parallel to this trend is the increased number of websites facilitating these Colombian-American matches. This dissertation investigates the agency of Colombian women and American men who pursue romantic courtship through the services of International Marriage Brokers (IMBs) from the “Gendered Geographies of Power” (GGP) framework of analysis. It examines how both groups’ social locations, their positioning in multiple axes of differentiation including gender, nationality and social class, affects how and why they exert their agency across and within different geographic scales. Most importantly, it investigates the role the imagination plays (imagination work) in both men and women’s agency, an aspect of the GGP framework that has been under-researched and theorized to date. The research also finds that this imagination work is promoted and cultivated in deeply gendered ways by IMBs seeking to profit off this transnational courtship. Employing data collected via interviews and content analysis of IMBs’ websites, the dissertation analyzes comparatively the expectations each group (women, men and IMBs) bring to their imagination work and experiences of the courtship marketplace. A central question posed and answered in the dissertation is “What do women and men courting each other in cyberspace seek and do they find it?” The dissertation finds that the men seek “traditional” women and the women seek “liberated” less “macho” men. Ironically, the men find Colombian women who are among the most “liberated” women in their homeland but who downplay this aspect of themselves in order to strategically find a more modern man and migrate abroad where they expect to find greater personal and professional opportunities.