Most interpersonal communication course textbooks include a section or chapter on the topic of self-disclosure. Students are normally introduced to elements of self-disclosure, such as a definition, functions, or reasons for self-disclosure, risks of self-disclosure, and the role of self-disclosure in relationships. Historically, research on self-disclosure has focused on face-to-face interactions. Currently, however, technology is playing a pivotal role in relationship building, which ultimately affects the process and our understanding of self-disclosure (Gibbs, Ellison, & Lai, 2011). Published academic research lags behind technological innovations. Lagging yet further behind is textbook coverage of that research. For most undergraduates, technology and computer-mediated communication (CMC) play a prominent role in their social lives and, as a result, students express a natural curiosity about and interest in the role of technology in their relationships. Furthermore, issues of dating and attraction are highly relevant and appealing facets of interpersonal communication for undergraduates. Bridging issues of self-disclosure, CMC, and attraction provides a relevant context through which students can better understand disclosure processes. Like face-to-face disclosures, computer-mediated disclosures present privacy considerations, prompting the following questions: With whom should I share this information? What should I share? How much should I share? In particular, online dating sites are popular arenas for self-disclosure. People form relationships with individuals they do not know in the offline context (Gibbs et al., 2011). On these sites, self-disclosure is used as a strategy to reduce uncertainty about who the person behind the screen is and to develop a relationship. The goal of the activity described here is for students to understand self-disclosure theory through the practical application of online dating; to promote increased awareness of interpersonal communication processes in mediated contexts; and to enhance information fluency regarding the academic literature on interpersonal communication.