Regular instances of employee and petty theft seem to suggest that stealing is common. Certain situations make stealing an advantageous opportunity, and studies show that most people will steal under the right conditions. However, these "right conditions" vary widely among individuals and are a combination of biological, social, psychological, and situational factors. In an attempt to better understand the rationality of stealing, our research team applied evolutionary psychology principles to a social experiment involving gift card theft. To find trends in how people will steal when given the opportunity, we attempted to create these "right conditions" (which we believed would encourage theft by minimizing cost) so that we could measure how a random sample of subjects (male students on the Tempe campus of Arizona State University) responded to variation in benefit. We predicted that if the cost was kept low, and if some gift cards conferred greater advantages than others (by possession greater value or utility), then the more advantageous gift cards would be stolen at a higher frequency from the sample pool than less advantageous ones. The results show that our assumptions were wrong. Theft almost never occurred and the few cards that were stolen were not the more "rational" choices as predicted. The experimental design indicates a flawed understanding of how the subjects weighed the benefits and costs of stealing gift cards. One major issue is that we failed to consider pro-social behavior as the norm. We also neglected the evolutionary benefits of cooperative behavior while overemphasizing the evolutionary benefits of theft. A more thorough and nuanced examination of the literature must be performed to avoid these fundamental flaws in the experiment in the future. The experiment also suffered from issues which might have inadvertently discouraged theft including the location, population, presence of other students, and time given to contemplate theft. If we wish to truly examine trends in theft to see if there is a trend towards the rational theft model we proposed, we must work with a population in which individuals already have a propensity to steal, the benefit is sufficiently high, and social pressures to be cooperative are low.