Anyone with a restricted amount of discretionary income hopes to get the very most utility out of every purchase. The present research was conducted to examine and explore one potential shortcut to making satisfying purchases, namely opting to choose experiential over material purchases. Experiences, purchases made with the intention of experiencing some event, like vacations or a meal at a restaurant, have been shown to be more satisfying than material possessions, purchases made with the intention of ownership and possession, like clothing or electronic gadgets (Van Boven & Gilovich, 2003). Although several explanations for this finding have been offered, to date little research has examined the underlying mechanisms. The present dissertation offers evidence across 14 studies in support of two such mechanisms. First, the evaluation of material possessions tends to rely on comparisons -- comparisons to unchosen options, to the new models now available, to the possessions of a friend. Experiences, on the other hand, tend to be evaluated largely on their own merits. As a result, people tend to engage in different decision-making strategies, opting to maximize material purchases and satisfice experiential purchases. The decision process is thus more difficult for possessions, and the unchosen options are more likely to linger in memory, increasing the possibility of regret, and diminishing present satisfaction. Furthermore, because comparisons are more relevant to the evaluation of possessions, negative comparative information has a greater hedonic impact for possessions than for experiences. A second reason that experiences are ultimately more satisfying has to do with their relationship to the self-concept. Because we define ourselves as a collection of memories, and, unlike possessions, experiences exist primarily in memory, experiences form a greater part of the selfconcept. What's more, the motivation to protect those memories helps to explain why experiential purchases are more satisfying. Additional evidence shows that, although the distinction between material and experiential purchases is sometimes murky, this ambiguity can be advantageous. Focusing on the experiential aspects of a purchase can obviate some of the negative consequences associated with material purchases. The implications of these findings are discussed.