This study analyzes the impact of the COVID-19 pandemic on subjective well-being as measured through Twitter for the countries of Japan and Italy. In the first nine months of 2020, the Twitter indicators dropped by 11.7% for Italy and 8.3% for Japan compared to the last two months of 2019, and even more compared to their historical means. To understand what affected the Twitter mood so strongly, the study considers a pool of potential factors including: climate and air quality data, number of COVID-19 cases and deaths, Facebook COVID-19 and flu-like symptoms global survey data, coronavirus-related Google search data, policy intervention measures, human mobility data, macro economic variables, as well as health and stress proxy variables. This study proposes a framework to analyse and assess the relative impact of these external factors on the dynamic of Twitter mood and further implements a structural model to describe the underlying concept of subjective well-being. It turns out that prolonged mobility restrictions, flu and Covid-like symptoms, economic uncertainty and low levels of quality in social interactions have a negative impact on well-being.