There is a need for Singapore bloggers to be aware of legal issues arising from their online diaries, particularly in the light of the recent cases involving seditious remarks made online by bloggers that resulted in jail terms and fines; and earlier in the year, a dispute arose over allegedly defamatory speeches made by a blogger about A*STAR’s Chairman, Philip Yeo, which was resolved amicably, but not without an apology. The threats of legal repercussions in the form of civil lawsuits and criminal charges serve as reminders of the potential legal problems that can arise from blogging, and indeed from any online activity, such as chat rooms, that involves the expression of opinions and views. Most bloggers treat their blogs as merely an online version of their personal diaries or journals. However, they often forget that the private-public distinction between keeping a written diary and one that is open to public viewing, can give rise to civil and criminal liability. This paper will consider some of the potential legal issues that may arise. Its aim is to create awareness and care, as well as to highlight sensitivities, but not to the extent that it may impact, to any significant extent, the greater freedom of expression that so many of us take for granted when navigating cyberspace.