When making decisions, people often anticipate the emotions they might experience as a result of the outcomes of their choices. In the process, they simulate what life would be like with one outcome or another. We examine the anticipated and actual pleasure of outcomes and their relation to choices people make in laboratory studies and real-world studies. We offer a theory of anticipated pleasure that explains why the same outcome can lead to a wide range of emotional experiences. Finally, we show how anticipated pleasure relates to risky choice within the framework of subjective expected pleasure theory.