This chapter presents a set of scenarios involving the GoPro wearable Point of View (PoV) camera. The scenarios are meant to stimulate discussion about acceptable usage contexts with a focus on security and privacy. The chapter provides a wide array of examples of how overt wearable technologies are perceived and how they might/might not be welcomed into society. While the scenario is based at the University of Wollongong campus in Australia, the main implications derived from the fictitious events are useful in drawing out the predicted pros and cons of the technology. The scenarios are interpreted and the main thematic issues are drawn out and discussed. An in depth analysis takes place around the social implications, the moral and ethical problems associated with such technology, and possible future developments with respect to wearable devices.