The ongoing ‘enhancement’ debate pits critics of new self-shaping technologies against enthusiasts. One important thread of that debate concerns medicalization, the process whereby ‘non-medical’ problems become framed as ‘medical’ problems. In this paper I consider the charge of medicalization, which critics often level at new forms of technological self-shaping, and explain how that charge can illuminate – and obfuscate. Then, more briefly, I examine the charge of pharmacological Calvinism, which enthusiasts, in their support of technological self-shaping, often level at critics. And I suggest how that charge, too, can illuminate and obfuscate. Exploring the broad charge of medicalization and the narrower counter charge of pharmacological Calvinism leads me to conclude that, as satisfying as it can be to level one of those charges at our intellectual opponents, and as tempting as it is to lie down and rest with our favorite insight, we need to gather the energy to have a conversation about the difference between good and bad forms of medicalization. Specifically, I suggest that if we consider the ‘medicalization of love,’ we can see why critics of and enthusiasts about technological self-shaping should want (and in some cases have already begun) to distinguish between good and bad forms of such medicalization.