Culture is not a predetermined, static, bounded unit. Both its boundaries and what is considered cultural difference are constructed through social processes. Ray McDermott and Herve Varenne (1995) argue that only certain differences are noticed, usually according to what is regarded as meaningful difference in one's own society. For example, in a society where everyone uses sign language, there is no meaningful difference between ability and inability to hear: because hearing does not matter in daily communication, its absence is not noticed or identified as different. That is, it is the social environment that singles out and marks certain differences as meaningful. This article examines the act of ''learning another culture'' through simulation, which highlighted the very ''cultural difference'' it was trying to bridge through the process of learning. Based on an ethnographic investigation of experiential learning of another culture during a college alternative break trip, this article shows that learning a different culture involves conflating and shifting between two subject positions--that of the people in the target culture and that of the learning self--highlighting the difference between the two subject positions more than bridging them. That is, Neriko Doerr argues that learning another culture did two fundamental things: (1) it highlighted the very difference between the cultures through the learner occupying what Doerr calls ''double subject positions''; and (2) it marked the meaningfulness of that difference. The ethnographic data for this article derives from an alternative break trip to a farm in the northern United States in March 2011, which included experiencing a simulation of life in poverty in rural Poland as part of an educational program for learning about global poverty, sustainable development, and humanitarian aid. The farm was run by a nonprofit organization (NPO). The trip participants were students and chaperones who were all deeply involved in community service, and Doerr, a researcher. This article examines three activities done on the trip--play-acting assigned roles, cooking dinner as poor Polish farmers, and stealing potatoes at the market--and suggests that their experiential learning of a different culture involved conflating and shifting between two subject positions: the poor Polish farmers and American college students/chaperones. As the difference was viewed hierarchically based on wealth disparity, this article also suggests a pedagogy of the privileged, a critical practice that seeks to involve students in identifying and working to reduce such hierarchy.