Temporal variations in loneliness at the individual and population level have long been reported in longitudinal studies. Although the evidence is limited due to methodological distinctions among studies, we broadly know that loneliness as one ages is a dynamic experience with people becoming more or less lonely or staying the same over time. There is, however, less evidence to understand individual variations in loneliness over shorter periods of time. This paper reports on one element of a small mixed method pilot study to investigate seasonal variations in loneliness over the course of one year and to test the effectiveness of tools used to collect data at repeated short intervals. Our findings confirm that loneliness is dynamic even over shorter periods of time with participants reporting to be lonelier in the evenings, weekends and spring-summer period. Data measures were at times problematic due to language and/or interpretation and reinforce the relevance of reviewing the more common approaches to studying loneliness to more effectively capture the complex and individual nature of the experience.