"How can HCI alleviate homelessness?" This was a question I and two cohorts addressed. We reasoned that the 'most likely' approach most others would take would be to develop a social network for the homeless (or caretakers of the homeless) or volunteers. We looked instead to create empathy by giving our users a 'virtual' experience of homelessness. As we approached this idea through games, we could achieve an intellectual appreciation of homelessness, but not necessarily the 'feeling.' We ended up moving way "outside the box" to create a 'monument' to the homeless, that took users through a narrative of shame, fear, confusion, and finally, resolution, kindness, and support for fellow humankind.