Romance in late capitalism is both more and less economically motivated than in the Industrial past as partners now search for “pure” romance among a staggering rise of digital platforms enabling matches across class and social positions like never before. This project maps the changing contours of intimacy and commerce and empirically systematizes transactional romances. I examine how partners transact emotions, time, resources, money, and sex; how they negotiate the terms of exchange against the widespread middle-class ideal of pure relations and the stigma of sex work, and how they manage and contest class and gender power inequalities. Based on the systematic comparison of “aspirational dating” in two contexts, the U.S. and the Balkans, I seek to identify patterns of transactional romance across a range of cultural norms, gender constraints, and economic opportunities. Through a comparative sociology of romantic markets, I develop a theory of the social creation of sexual morality.