This article explores the long-term impact of the COVID-19 pandemic on everyday life through a qualitative research study focusing on the role of age in managing uncertainty. Grounded in a cultural and symbolic perspective on risk, the study examines how rituals, emotions, and cultural contexts shaped the experiences of individuals aged 15–34 in Milan, Italy, as they navigated daily risks. Drawing on 42 semi-structured interviews conducted between September 2022 and May 2023, the findings reveal that age significantly influenced how young people navigated post-pandemic uncertainties. The youngest participants often felt fear and anxiety, mainly due to concerns for others’ well-being, coupled with a strong need for social interaction and community. In contrast, slightly older young professionals showed a more complex emotional response characterised by caution, frustration, and empathy. Across all age groups in the sample, daily routines and social interactions kept reinforcing societal norms and hierarchies, particularly concerning generations and family dynamics within Italian culture, with a specific emphasis on vulnerable populations, namely older adults. These findings highlight the importance of considering both life stage and cultural context when analysing responses to uncertainty. Still, they underscore young people’s adaptability as both a reactive process and a forward-looking one involving agency. This flexibility was particularly evident in the context of the COVID-19 pandemic in the Lombardy region of Italy, where the virus spread earlier and with more severe consequences than in most parts of the Western world.