Direct messaging allows Internet celebrities to establish an immediate and intimate connection with their fans by offering personalized communication that can blur the line between public and private interactions. This chapter explores how direct messaging helps celebrities develop a fanbase, promote their creative works, and manage their reputations during moments of crisis. This mode of reach is often part of a more detailed marketing campaign or public relations strategy by giving fans the illusion of closeness with their favorite celebrity. We need to examine the ethical considerations as they relate to this mode of reach to understand how we can avoid manipulating others or miscommunicating our intentions. Using dramaturgical theory allows us to see how we (and, in turn, celebrities) perform their public and private personas via direct messaging. Average Internet users need to develop critical media literacy skills to navigate these exchanges to better appreciate the purposes behind these conversations.