With the global proliferation of ‘sugar dating’ websites, the phenomenon of sugar dating is increasingly debated. Sugar dating is described by the sites themselves as dating arrangements based on an exchange of intimacy and companionship for financial or other forms of support. Since sex is often part of these arrangements, claims are widespread – while disputed – that sugar dating amounts to prostitution. My own and Sofia Strid’s research shows that although sugar dating indeed constitutes an expansion of the sex industry, it also challenges common divisions between ‘regular’ relationships and sexual commerce. The way that many sugar dating arrangements are located at the border of the transactional and the authentic calls for new conceptualizations of the meaning of commercialization in the sphere of intimacy. This paper draws on semi-structured interviews and a survey questionnaire with Swedish ‘sugar daddies’ and female ‘sugar babies’ with experience of heterosexual sugar dating. It addresses a theme that emerges in the accounts of both ‘sugar babies’ and ‘sugar daddies’: the compensated form of dating offered by the sugar dating contract is described as positively experienced by several participants due to its bounded character, as compared to regular romantic relationships and dating. Previous research on the so-called girlfriend experience, an increasingly popular service offered by some escort sex workers, has highlighted that many male purchasers of sex appreciate the bounded form of intimacy offered in these encounters. The girlfriend experience provides an experience of genuine or quasi-genuine mutuality but without the demands, responsibilities and vulnerabilities that come with uncompensated relationships. The ‘sugar babies’ participating in our study reported a wide variety of experiences of sugar dating, including unequivocally negative experiences. However, a theme that stands out as interesting in our data is that not only the ‘sugar daddies’ but also several of the ‘sugar baby’ participants indicated an appreciation of the bounded form of intimacy that they felt was offered in sugar dating arrangements: a lack of demands and emotional involvement was described as positive aspects of sugar dating as compared to non-compensated dating. In this paper this theme is analysed in light of neoliberal transformations of social relationships bolstering an instrumentalizing attitude to relationships including sex and intimacy. Drawing on Eva Illouz’s work on the contemporary structural conditions of love, I address the participants’ reported appreciation of the bounded and contractual features of sugar dating arrangements as mirroring the fact of an increasingly precarious regular dating ‘market’, where vulnerability and uncertainty prevail. I also draw on Antony Giddens’ notion of the pure relationship, conceptualizing the preference for a contractual intimate arrangement regulated by objective, external factors (material compensation) as a way of avoiding the vulnerabilities of a pure relationship based solely on the parties’ subjective experience that the relationship is intrinsically satisfying.