This chapter offers a theory of how we can cultivate our passionate attachments. It is composed of two elements. First, it defines what it is to cultivate our passionate attachments, showing what counts as passionate self-cultivation in terms of its necessary and sufficient conditions. Second, it explains how we can actively cultivate our passionate attachments, putting to work general Hellenistic observations on self-directed character change by applying them to how passionate self-cultivation functions specifically. To do this, 5.1 offers examples (and counterexamples) of passionate self-cultivation to show what distinguishes passionate self-cultivation from other – ostensibly similar – ways of cultivating the self, such as moral or prudential self-cultivation. Following this, 5.2 explains how such deep-seated character operates, comparing the processes that apply to all kinds of self-cultivation to those that apply to passionate self-cultivation specifically. These sections build on my account of what distinguishes our passionate attachments from other deep-seated action-guiding considerations (1.5), show how passionate self-cultivation differs from the other types of self-shaping that philosophers have traditionally been interested in (2.2), and connects this to the reasons we have to think that this kind of self-cultivation is especially valuable (2.3). With this theoretical account in place, we will be ready to return to Foucault’s pratiques de soi and Hadot’s exercices spirituels in Chapter 6, where I show how these exercises offer a practical method that can be applied to the cultivation of our passionate character.