Since gaining independence in 1965, Singapore has become the most trade-intensive economy in the world and the richest country in Southeast Asia. This transformation has been accompanied by the emergence of a deep generational divide. More complex than simple disparities of education or changes in income and consumption patterns, this growing gulf encompasses language, religion, and social memory. This book explores how expectations and obligations between generations are being challenged, reworked, and reaffirmed in the face of far-reaching societal change. The family remains a pivotal feature of Singaporean society and the primary unit of support. It focuses on the middle generation, caught between elderly parents who grew up speaking dialect and their own children who speak English and Mandarin. In analyzing the forces that bind these generations together, the book deploys the idea of an intergenerational “contract,” which serves as a metaphor for customary obligations and expectations. It examines the many different levels at which the contract operates within Singaporean families and offers striking examples of the meaningful ways in which intergenerational support and transactions are performed, resisted, and renegotiated. The book provides insights into the complex interplay of fragmenting and integrating forces and makes a critical contribution to the study of intergenerational relations in modern, rapidly changing societies and the challenges that Singaporean families face in today's hypermodern world.