Since the pandemic, older adults have become more willing to adopt video calling to stay connected with loved ones. Prior research indicates that video-mediated communication has the potential to facilitate perceived closeness to interaction partners, but may present difficulties for older adults of advanced ages in terms of usability and accessibility, challenging them to benefit as much from the distance-reducing properties of video calling as younger older adults. However, the video-calling experiences of those aged 75+ and the specific conditions enabling them to overcome medium-related challenges, especially in informal settings, have remained relatively unexplored. This study aimed to gain deeper understanding of the circumstances that shape perceptions of distance and closeness during the video-mediated interactions of this age group. Using grounded theory analysis of 108 interviews, it identified five key properties and three roles ascribed to video-mediated communication, revealing that respondents’ perceptions of distance and proximity were contingent upon their appraisals of video calling’s properties in light of their broader emotional, relational and interactional contexts. The findings confirm video calling’s potential to reduce perceived distance in the informal encounters of individuals aged 75+. Nevertheless, fear of substitution of in-person contacts may overshadow video calling’s positive aspects, undermining any perceived closeness to interaction partners. By unveiling the mechanisms central to empowering or impeding these individuals in navigating medium-related challenges and overcoming perceived distance during video-mediated interactions, this article sheds light on the age-related specificity of their video-calling experiences and offers valuable starting points for developing strategies to help them benefit fully from video-mediated social-interaction opportunities.