Urban planning has, in its rich history, often been reviewed from the perspective of different philosophical, ideological and methodological approaches by planners, architects and social scientists. In this paper, we aim to highlight the debate on urban planning in the context of planning history and to address some of the most fascinating questions asked in the urban planning literature. We focus on 7 FAQs in urban planning, while we address 7 differently given answers for each question. Therefore, our tree-like exercise consists of 7 × 7 = 49 different approaches to urban planning. Our questions are derived from planning theory and practice, planning methodology and techniques, urban development, urban management and urban future. The paper will be concluded with a concise speculative agenda for the future of urban planning.