Sugar dating is a complex phenomenon that unfolds on a continuum between traditional dating and sex work. Existing research shows that sugar dating is often portrayed as rife with potential physical and social risks, and from a societal standpoint, it is also often characterized as a risky activity, particularly for young individuals. In this article, we investigate the emergence of these risks and how young sugar daters strategize to minimize them. The findings demonstrate that risk in sugar dating is influenced by complex social and cultural contexts, where especially the stigmatized nature and gendered storyline of sugar dating constitute risks for young sugar daters. These risks are further shaped by the cultural construction of late-modern sexuality, which favours elusive and volatile sexual relations combined with a desire to explore while being young. The young women in this study view sugar dating as a temporary activity that they do not imagine themselves engaging in when they get older. They associate sugar dating with the phase of youth, but unlike other types of youth risk-taking, sugar dating does not occur within the social context of peers. Instead, risk management in the context of sugar dating primarily becomes an individual responsibility, as involving others is perceived as carrying substantial social risks of being labelled as sexually immoral. The study underscores that risk in sugar dating does not exist in a vacuum; rather, it is intertwined with complex social and cultural contexts surrounding sugar dating. By shedding light on these intricate factors, our research contributes to a comprehensive understanding of the lived experiences and dynamics of risk management within the realm of sugar dating.