In this multiple case study of two high schools in the United States, we use interview and focus group data to examine the experiences of teen-age students when they friend and interact with teachers, high school administrators, parents, and other adults on social network sites (SNS). We identify several types of teen-adult interactions on SNS, including finding information, community building, and mentoring online skills, and we connect these findings to literature on homophily and context collapse. We also report on social media norms and policies of the schools where our fieldwork was conducted. We discuss how organizational policies surrounding social media use can inhibit or reinforce the development of age-homophilous networks and thereby encourage or reduce opportunities for teen-adult interaction online. Finally, we conclude that boundary work associated with managing these complex social experiences, though awkward at times, can be an important learning experience for adults and young people alike. Copyright is held by the owner/author(s).