Several recent cases have highlighted the range of legal controls that can be applied to expression on social networks and other amateur digital content. This article identifies three trends in the regulation of digital communications. First, such communications are subject to a wide range of laws, including those primarily regulating the mass media, public order and targeted communications. Second, the persistence and searchability of digital messages make such communications more likely to come to the attention of litigators and prosecutors. Thirdly, that the established approach to freedom of expression under Article 10 of the ECHR tends to protect speech that is deemed to be of “high value”, and therefore does little to protect much internet content. This article calls for some greater protection to be afforded to communications that are casual and amateur. The freedom to converse outlined in this article does not call for absolute protection, but seeks to ensure that any controls on expression are proportionate. In particular, alternatives to the criminal law are considered.