Assisted living technologies have been introduced to support patients in staying in private homes longer in the digital era. Despite the convenience they offer, various factors influence patients’ adoption of them, with privacy being a crucial consideration. Therefore, it is imperative to gather information on patients’ privacy attitudes to effectively implement health monitoring systems. From another perspective, collecting patients’ privacy attitudes and constructing privacy predictive models empower monitoring systems to make informed decisions in situations where patients lose their capacity. However, the discrepancy between privacy attitudes and privacy decisions in real-life situations, known as privacy paradox, can impact the predictive performance of these models. In this paper, we present the results of two experiments, one conducted via questionnaires, and the other one conducted via a combination of questionnaires and a VR platform. We investigate whether participants’ situation-specific privacy attitudes in VR and questionnaires deviate from their stated privacy attitudes. The results of the studies have reflected two findings. First, privacy paradox phenomenon exists, and it was observed among most of the participants. Second, participants’ privacy attitudes exhibited variability during all phases of the study. The findings suggest avenues for future research.