With the experiential turn in Human–Computer Interaction (HCI), academics and practitioners broaden their focus from mere task-fulfillment (i.e., the pragmatic) to a holistic view, encompassing universal human needs such as relatedness or popularity (i.e., the hedonic). Accordingly, many theoretical models of User Experience (UX) acknowledge the hedonic as an important aspect of a product’s appeal. In choice situations, however, people (i.e., users, consumers) overemphasize the pragmatic, but fail to acknowledge the hedonic. The present research explores the reasons for this phenomenon. We suggest that people attend to the justifiability of hedonic and pragmatic attributes rather than to their impact on experience. In other words, they choose what is easy to justify and not what they enjoy the most. Since providing justifications is easier for pragmatic than hedonic attributes, people arrive at a primarily pragmatic choice, even if they would feel better with the hedonic. We explored this assumption, called the Hedonic Dilemma, in four empirical studies. Study 1 (N = 118) revealed a positive correlation between the need for justification and pragmatic choice. Study 2 (N = 125) explored affective consequences and justifications provided for hedonic and pragmatic choices. We further explored two different ways to reduce the Hedonic Dilemma. Study 3 (N = 178) enhanced the justifiability of hedonic choice through product information which suggested hedonic attributes as legitimate. In consequence, hedonic choice increased. Study 4 (N = 133) manipulated the need for justification through framing the choice context. A significant positive effect of a “low need for justification” frame on purchase rates occurred for a hedonic but not for a pragmatic product. Our research has a number of implications, reaching from how to elicit requirements to general strategic considerations when designing (for) experiences.