The first chapter of my dissertation shows that, in general, pain is more contrast-dependent than pleasure. For example, I find that losing time in traffic is less annoying if one’s friend got stuck in traffic for longer, but the happiness from saving time remains relatively undiminished if one’s friend saved even more time. I also show an important implication of this asymmetry: because contrast lowers the impact of negative outcomes more than that of positive outcomes, risky propositions become more attractive in the presence of extreme comparisons. I demonstrate this with incentive-compatible studies of monetary choices, as well as with other choice scenarios. For example, I find that people are more likely to endorse an experimental drug that may increase or decrease survival rate if it is evaluated in the presence of another drug that could have affected the survival rate much more significantly in either direction. I show that the asymmetry occurs because people are much more likely to pay attention to comparisons when evaluating negative outcomes, such that prompting them to pay attention to comparisons eliminates the asymmetric contrast effect. For instance, the hedonic impact of losing money, but not gaining money, is weakened if losses and gains are evaluated in the context of a much larger sum; however, prompting people to pay attention to the larger sum leads them to experience contrast regardless of whether they evaluate gains or losses.