Youth engagement is a critical dimension of youth development where the youth population engages in social action. In Kuwait, the patriarchal and hierarchical social structure has rendered youth participation and civic and community engagement a slow and elusive experience with notable effects on the economic trajectory of the country in an era of “youth bulge” in the Kuwaiti society. Despite an extensive cradle‐to‐grave welfare system, the presence of skilled and knowledge workers among the Kuwaiti population is negligible, undermining long‐term prospects of economic growth and development. As a result of increased use of the Internet and social media, there are growing calls for greater freedoms and reform of the traditional socioeconomic structure among the youth. Contextualizing from a historical perspective, this article comparatively analyzes the various contexts of youth participation in the pre‐ and post‐oil Kuwait, examines the socioeconomic transformation of Kuwait during and after the Gulf War of 1991, and reviews the current challenges of community participation among the youth and outlines a series of recommendations for the way forward.