We examine financial challenges of purchasing items that are readily-available yet symbolic of loving relationships. Using weddings and funerals as case studies, we find that people indirectly pay to avoid taboo monetary trade-offs. When purchasing items symbolic of love, respondents chose higher price, higher quality items over equally appealing lower price, lower quality items (Study 1), searched less for lower priced items (Study 2) and were less willing to negotiate prices (Study 3). The effect was present for experienced consumers (Study 1), affectively positive and negative events (Study 2), and more routine purchase events (Study 3). Trade-off avoidance, however, was limited to monetary trade-offs associated with loved ones. When either money or love was omitted from the decision context, people were more likely to engage in trade-off reasoning. By abandoning cost-benefit reasoning in order to avoid painful monetary trade-offs, people spend more money than if they engaged in trade-off based behaviors, such as seeking lower cost options or requesting lower prices.