In this paper we present a longitudinal field study of “kiss messaging interface” designed and developed for people in long distance relationships (LDRs). Mediators of intimacy are a novel class of telecommunication systems that enable people in LDR to express affection and intimacy despite being non co-located. To better understand how people experience these interfaces in the realistic and outside the lab environment, and how they blend in the users context, longitudinal field studies are required. To address the need of studying the mediators of intimacy in their natural usage context, a longitudinal field study is performed and design insights are explored under actual daily contexts over a threeweeks period. Also the study on the mediator of kiss technological probe, provided us with the user expectations from the mediators of the kiss which could also contribute towards the design of other similar technologies.