Situationists International (SI) was a collective of avant-garde artists and intellectuals (1957 - 1972) which explored concepts and theories for liberating people from the homogenisation of everyday life. The group critiqued the consumerist society’s orchestration of everyday life towards economic productivity, and the role of rational planning and New Town development in Europe within. This study examines Hong Kong’s New Towns through the lens of the Situationists, to evaluate whether their urban planning limits the potential for spontaneous social interaction and exacerbates social isolation. It aims to identify the latent opportunities for creating more dynamic communities and locate places that could facilitate unplanned journeys or activities. The work has developed an evaluation framework for urban qualities based on the Situationist concepts and applied it to a comparative study of Hong Kong’s Central district and Ma On Shan New Town. The research used documentation of residents’ everyday behaviours to analyse their responses to different spatial configurations, identifying the potential value of different urban elements in shaping everyday life. The findings challenge current urban design models in Hong Kong and advocate for a human-centric approach that prioritises individual freedom and creativity. The study underscores the importance of creating urban spaces that stimulate social interaction and foster a sense of community.