What is vaguebooking? You’ve probably heard the term being bandied about on social media, but do you understand what it actually means? In this article, we’ll explain what vaguebooking is, and give specific examples of vaguebooking so that you’ll be able to recognize it when you see it. What Is Vaguebooking? There was a time when people kept diaries in order to express their innermost thoughts and feelings.