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 limited. In this paper, we provide evidence that teen–robot interaction is a unique area of inquiry and designing for teens is categorically different from other types of human–robot interaction. Using human-centered design, our team is developing a social robot to gather stress and mood data from teens in a public high school. To better understand teen–robot interaction, we conducted an interaction study in the wild to explore and capture teens’ interactions with a low-fidelity social robot prototype. Then, through group interviews we gathered data regarding their perceptions about social robots. Although we anticipated minimal engagement due to the low fidelity of our prototype, teens showed strong engagement and lengthy interactions. Additionally, teens expressed thoughtful articulations of how a social robot could be emotionally supportive. We conclude the paper by discussing future areas for consideration when designing for teen–robot interaction.