While scholars in technical communication have examined on theoretical concerns of post humanism, less work has focused on designing for engaging experiences between humans and nonhuman agents like robots. In this research article, we present findings from a project investigating the possibility of designing a social robot to help measure teen stress. To explore design possibilities, we conducted a series of participatory design sessions with teens to envision the design of a social robot to measures stress. The findings from the study include how teens react to existing robots, how teens conceptualize robots that might live in their schools through storyboarding and group discussion, and reactions to an emerging design of a low fidelity robot. In our discussion, we reflect on implications for designing social robots for and with teens, considerations for studying engaging relationships, and reflections on methodological choices of participatory design.