This thesis contributes to a small body of research that examines the ‘sugar baby phenomenon’ in a Canadian context. To date, most of what is known about sugar babies’ experiences is through anecdotal accounts filtered through the media. By drawing on the content of one popular sugar baby forum, as well as data gathered from two in-depth qualitative interviews with two active sugar babies, this thesis explores the lived experiences and perceptions of the participants. In particular, this study seeks to determine whether sugar babies articulate shared motivations; how they navigate sugar dating’s blurring of traditional romance and sex work; and how they exercise power and agency within their relationships. Key findings are that sugar dating’s blend of conventional dating and sex work creates a new conceptual space that both enhances the degree of power and agency exercised by sugar babies, and constrains it in ways both traditional and novel.