The research at-hand examines fundamental aspects of relational communication in online computer-mediated communication (CMC) channels. Specifically, the realm of online dating is investigated through the lens of imagined interactions (IIs) to create pathways for research, and better understanding of the cognitive strategies people utilize during intimate CMC encounters. An exploratory sequential mixed methods design utilized in-depth, semi-structured qualitative interviews (n = 12) to inform the creation of a quantitative online survey (n = 220) that statistically investigated the online dating process. Five major themes (honesty, trust, stigma, overall experience, and imagined interactions) resulted from the qualitative thematic analysis; these themes served as the basis by which counterpart factors were created in the quantitative scales. The findings from the quantitative analyses indicate that frequency and retroactivity, as characteristics of online IIs, and self-understanding, relational maintenance, catharsis, and compensation as interpersonal functions of IIs, are significantly related to trust, stigma, and the overall experience users associate with online dating.