Studying the social interactions and relationships of young adults in Singapore, this paper seeks to understand the issue of social disconnection and how design shapes them. Young adults face the challenge of navigating the complex lifestyle of a smart city while balancing their ever expanding and fluctuating social network. As such, it causes them to feel disconnected in their social interactions and relationships. By considering these questions: What does it mean to be connected? What is the role of product design in people’s relationships? Why do young adults feel disconnected in a technologically connected society? How can design establish a truly connected society? it will evaluate how products could be designed and created for genuine interactions and fulfilling relationships. From the surveys, interviews, observations, case studies and literature readings in this study, it reveals the social disconnection young adults face in a connected city, how they navigate in a technological environment, and how experiences are designed for connection. It also shows that design plays a vital role in tackling the social disconnection young adults face. Designing with a human-centric approach not only creates an opportunity for people to create meaningful relationships using technology, but also maintains the spontaneous and fluid elements of social connections through prompting interactions. Additionally, it has been found that design is only a platform where they can initiate these interactions and relationships, the decision to disconnect remain with the human user as much as devices have been designed to lead to certain decisions being made.