This chapter discusses the way essays construct and perform the relationship between the self and the other. The ‘I’ of the essay – the speaking voice of the essayist – is central to the widely accepted idea of the essay as self-portrait. Through a discussion of the work of Michel de Montaigne, Claudia Rankine, and Brian Dillon, among others, the chapter argues that while the ‘I’ of the essayist is fundamental to our reading and writing of essays, the self in the essay is inevitably engaged in relations of affinity and contestation with others. In this sense, we can think of the ‘I’ of the essay as collaborative rather than simply expressive, and as engaging in communal spaces rather than being exclusively immersed in individual concerns. This, it is argued, has implications for how we think of the essay, both as a literary form as well as a form that may be significant in cultural and political exchanges.