In the last decades of the 20th century, the patterns of urban shrinkage defined a worldwide phenomenon. They are visible in all developed regions, especially in Central and Eastern Europe, on the background of the economic growth trajectories and social health improvements. Despite this fact, the public discourse in a post-socialist country such as Romania is only focused on urban decline and its demographic dynamics sliding, when in fact urban shrinkage is more advanced, even to the point of becoming a selective phenomenon in developed countries such as The Netherlands. Our focus on urban shrinkage was driven by the fact that Romania can develop a policy framing regarding urban shrinkage, using example practices from a developed country such as The Netherlands. Moreover, it can learn how to deal with urban shrinkage effects by establishing certain differences which can cope with veritable lessons from both sides. This paper firstly investigates the urban shrinkage phenomenon observed in three cities in Romania and in three cities in The Netherlands. Secondly, it presents an analysis of demographic statistical data using the shift-and-share method to emphasize the persistence of urban shrinkage in the age structure of the total population of shrinking cities from both regions. Thirdly, it offers some lessons from both countries, finally presenting a mutual learning framework that can be applied to other regions in Europe.