This paper discusses the 'art' of prototypical ‘Pick-Up Artists’ (PUAs) in the UK, i.e. males who attempt to be successful at ‘alluring’ women, the roots of which are generally believed to reside in the interaction itself. The focus is thus on how PUAs actually play their game, as gamblers in high-stakes games where hazardous plays – which comprise im/politeness and in/equity issues– can entail high payoffs.