Recent years have seen a proliferation of secure device pairing methods that try to improve both the usability and security of today's de-facto standard - PIN-based authentication. Evaluating such improvements is difficult. Most comparative laboratory studies have so far mainly focused on completeness, trying to find the single best method among the dozens of proposed approaches - one that is both rated the most usable by test subjects, and which provides the most robust security guarantees. This search for the "best" pairing method, however, fails to take into account the variety of situations in which such pairing protocols may be used in real life. The comparative study reported here, therefore, explicitly situates pairing tasks in a number of more realistic situations. Our results indicate that people do not always use the easiest or most popular method - they instead prefer different methods in different situations, based on the sensitivity of data involved, their time constraints, and the social conventions appropriate for a particular place and setting. Our study also provides qualitative data on factors influencing the perceived security of a particular method, the users' mental models surrounding security of a method, and their security needs.