Today's teens will most likely be the first generation to spend a lifetime living and interacting with both mechanical and social robots. Although human-robot interaction has been explored in children, adults, and seniors, examination of teen-robot interaction has been minimal. Using human-centered design, our team is developing a social robot to gather stress and mood data from teens in a public high school. As part of our preliminary design stage, we conducted a interaction pilot study in the wild to explore and capture teens' initial interactions with a low-fidelity social robot prototype. We observed strong engagement and expressions of empathy from teens during our qualitative, interaction studies.