The present study seeks to apply the interpersonal construct of imagined interactions (IIs) to CMC, specifically in the realm of online dating, to explore the nature of imagination work while using dating apps and sites. The relationship between the characteristics and functions of IIs and the degree to which they predict dating themes of honesty, trust, stigma, and overall experience was tested. Multiple regression analyses were carried out to locate the specific characteristics and functions of IIs that are activated during the online dating process. The adapted survey of imagined interactions (SII) proved to be a reliable measure of all characteristics and functions when applied to the context of online dating themes of honesty, trust, stigma, and overall experience. Several reliable psychometrics for investigating imagined interactions within the context of online dating have been established, and support for the hyperpersonal communication model is discussed.