This exploratory paper aims to discuss how community is fostered in semi-public restrooms on a college campus. While previous research has been undertaken in similar semi-private environments, this paper differs by simultaneously offering the researchers’ reflective insights in tandem with participants’ input on the research question. We begin by unpacking the challenges around Participatory Design (PD) activities that are undertaken in sensitive and private interior environments. Gathering perceptions of these sensitive spaces required methods that allowed for both anonymity and a communal approach through the use of provocative and evocative probes such as comment boxes and graffiti wall posters. This paper not only catalogues the findings of this research but also documents the difficulties in utilizing a participant-led approach, gaining access to sites and participants, and countering our own biases throughout the study’s construction. Through researcher accounts and participatory data analysis, the researchers offer a focused reflection on a possible new frontier for advancing PD methods in sensitive environments through playful probes. The contribution of this paper offers six lessons on the efficacy of using probes in semi-private environments, with playfulness as a primary driver of engaging participants.