Deception is typically regarded as a morally impoverished choice. However, in the context of increasingly intimate, connected and ramified systems of online interaction, manipulating information in ways that could be considered deceptive is often necessary, useful, and even morally justifiable. In this study, we apply a speculative design approach to explore the idea of tools that assist in pro-social forms of online deception, such as those that conceal, distort, falsify and omit information in ways that promote sociality. In one-on-one semi-structured interviews, we asked 15 participants to respond to a selection of speculations, consisting of imagined tools that reify particular approaches to deception. Participants reflected upon potential practical, ethical, and social implications of the use of such tools, revealing a variety of ways such tools might one day encourage polite behaviour, support individual autonomy, provide a defence against privacy intrusions, navigate social status asymmetries, and even promote more open, honest behaviour.