The “Right to the City” is a worldwide movement initiated by French sociologist and philosopher Henri Lefebvre in the 1960s. The premise of the movement is based on the concept that citizens have an unassailable right to build the city they live in, based on their needs and desires. In parallel the term “placemaking” was established as a response to modernist architecture and urban planning practices. Placemaking is a participatory process that integrates the ideas and skills of people who utilise the space in question and seek ways of improving it for their daily use and needs. The experiences of citizens coming from different social backgrounds and groups vary, however, as do their needs, making it pivotal to provide special attention to some groups during the process of placemaking. In practice, most activities initiated via top-down approaches fail to engage young people in a meaningful way. We have noticed, through our experiences, that there is a lack of understanding of young people’s needs and abilities, not to mention interests. In this chapter, we will discuss different approaches to playing that can help enable and empower young people. We believe these methods promote true engagement and have had a positive impact on their contribution in a placemaking project. In order to do so, we will specifically analyse and evaluate methods that involve playing as a means to encourage young people’s ideas and inspiration. The evaluated methods (three different games) are used in international projects (six different cases). The key aspects were to deal with the unimaginable, to understand what to change and, last but not least, who is going to have which role in the change. When evaluating the different methods, we will also look at the context cases alongside the needs of young people in participatory processes.