While social media is largely concerned with publicity, nearly every service also includes a private messaging facility. Chapter 6 begins with the failed attempt to send a lewd Twitter direct message that became known as the ‘Weinergate’ controversy. This is discussed in relation to the hyperpersonal model of communication, which explains how social media users try to exploit features like being able to edit messages to achieve communication goals that they cannot in face-to-face conversation. But messages also include timestamps, which are shown to be crucial in understanding Facebook Pokes. Additionally, users’ motivations are explored in this chapter, noting how social media relationships are maintained by disclosing personal information within private messages. While sharing such information publicly does not seem to have the same effect, this chapter also examines indirect messages or subtweets, and the varied impressions that they create of their senders. Furthermore, the appeal of social media is compared to social messaging services, where it is shown that users prefer the former for informational reasons, and the latter for social satisfaction. However, occasionally social messaging services are used for informational purposes, and the moral dilemmas created by rumour-spreading on WhatsApp during a security emergency is discussed.