One of the most important goals of humanity has always been happiness. In our daily life, happiness is conditioned by different variables, such as relationships with certain groups of individuals, health, security values, expectations, etc. Over the years, technology, especially digitalization, has revolutionized the world and changed our lives. In this context, empirical research on digitalization has grown enormously during the last decade; however, studies on the relationship between digitalization and happiness remain limited. As such, the objective of the present paper is to present an empirical investigation on the relationship between digitalization and happiness in the European Union (EU) during the period 2019–2021, before and during the COVID-19 pandemic. In this context, the link between the Digital Economy and Society Index (DESI) and World Happiness Index (WHI) globally for all EU countries, at the level of each WHI variable and at the level of geographical groups in the EU was analyzed using correlations. While the DESI indicator acts as a basis for policymakers, governments, regional administrators and public officials to invest in areas of priority with an evidence-based approach, the WHI indicator can be an important tool for guiding public policy and measuring its effectiveness. The results show that there was a positive and significant relationship between the two indicators at the level of EU countries in all three years. The results also show that in the Western and Northern regions of the EU, the relationship between the two indicators was stronger compared to the other regions. Thus, our study offers supporting arguments for the digital transformation of happiness and provides alternate methodologies and perspectives on the interactions between digitalization and happiness. Moreover, it can help policymakers direct their attention to the importance of digitalization for people’s happiness.