At what point is the line crossed between a series of humorous work pranks and workplace bullying? This question is actually more complex than it looks. Take the very well publicized office complaint case of David Thorne and Simon Dempsey—a story that has taken social media sites and the wider Internet by storm over the last couple of years. Although it has now been revealed that the interactions between Thorne and Dempsey are somewhat fictitious (loosely based on actual interactions between the author and a previous coworker), the behaviors and their ensuing complaints provide a lens from which this question can be considered.