In addition to the increased risk they face for social and academic problems, adolescents with Attention-Deficit/Hyperactivity Disorder (ADHD) must also contend with stigma attached to the disorder. For instance, youth prefer greater social distance from students described with ADHD symptoms than from peers with asthma (Walker, Coleman, Lee, Squire, & Friesen, 2008), and adolescents are also reluctant to engage in activities (e.g., go to the movies, study together) with a peer described with ADHD symptoms compared to peers described as obese or autistic (Law, Sinclair, & Fraser, 2007). Familiarity with individuals diagnosed with ADHD may influence adolescents' perceptions of their peers with ADHD, but the extant research on this relationship in adolescents is limited and mixed. The purpose of this study was to investigate middle school students' familiarity with ADHD, their willingness to engage in activities with a peer exhibiting ADHD symptoms, and how familiarity impacts their willingness to engage in a variety of activities with that peer. A sample of middle school students (N = 176) completed self-report measures of contact with ADHD and willingness to engage with a peer described in a vignette. Participants were randomly assigned vignettes describing either a peer displaying ADHD symptoms or a typical peer, employing a true experimental design. Middle school students expressed greater willingness to engage with a typical peer than one with ADHD symptoms overall. However, a significant difference (p < .05) was found only for academic activities, and not for social and recreational activities. This difference was present regardless of the inclusion of positive characteristics in the description of the peer with ADHD, suggesting that it is something about ADHD symptoms leading to middle school students' reluctance, not simply the lack of appealing characteristics. Additionally, approximately 70% of middle school students indicated some contact with ADHD, although familiarity with ADHD was not found to predict participants' willingness to engage in activities with a peer with ADHD symptoms. Implications for school psychologists and directions for future research are discussed.