Although taboo given the traditional Thai value of female sexual conservatism, sex work is a practice for which Thailand has gained international attention. As in other rapidly globalizing contexts, however, Thai youth are increasingly exposed to global values of gender equality, self-fulfillment, and personal choice. This may, in turn, alter youth perspectives of this taboo yet pervasive practice. To understand how Thai youth negotiate local and global values when considering sex work, this study examined the moral evaluations and moral reasoning of adolescents residing in variously globalized communities. Forty participants (20 adolescents in each a more and a less globalized Thai setting) participated in interviews in which they discussed their perspectives of sex work. Quantitative analysis of moral evaluations revealed that rural and urban adolescents alike deemed sex work as mostly morally wrong. Qualitative analysis of moral reasoning revealed that both participant groups prioritized Thai values of sexual purity for women, shame avoidance, and reputation maintenance. Yet distinct values were also endorsed across participant groups. Rural adolescents centered local values (e.g., relational choice, women’s dignity, Buddhist divinity) and urban adolescents drew heavily from global values (e.g., autonomous choice, romantic love, international reputation) when reasoning about the morality and immorality of sex work. Findings point to the manner in which contextual realities shape—and reshape—cultural values in this rapidly globalizing nation.