Cool can be thought about on three levels; the having of cool things, the doing of cool stuff and the being of cool. Whilst there is some understanding of cool products, the concept, of being cool is much more elusive to designers and developers of systems. This study examines this space by using a set of pre-prepared teenage personas as probes with a set of teenagers with the aim of better understanding what is, and isn’t cool about teenage behaviours. The study confirmed that teenagers are able to rank personas in order of cool and that the process of using personas can provide valuable insights around the phenomenon of cool. The findings confirm that cool is indeed about having cool things but in terms of behaviours cool can be a little bit, but not too, naughty.