It is often challenging to establish a good relationship between the green initiatives of urban citizens and local governments. Our aim is to gain a better understanding of how citizens and local authorities interact and how they can establish good relationships, relationships that contribute to the realization of the aims and interests of citizen initiatives and local governments. We analysed these relationships for five different initiatives, including the perspectives of initiators and civil servants. We hypothesized that an important challenge is to connect the initiative’s informal world and the formal world of local governments. Relationships can be problematic due to a lack of recognition and appreciation for the initiators on the part of the municipality, diverging ambitions or ideologies between the initiative and municipality or unreliable behaviour of initiatives in the view of civil servants. The results showed that a willingness to work together and developing trust are key conditions in developing good partnerships. Our study provide insight into how mutual trust can be developed. Developing a trustful relationship requires social competences. Trust building involves several social practices: establishing an emotional connection, ability and integrity, and aligning to each other’s expectations. Formal aspects of local governments, like rules and procedures, are not a major problem in the development of initiatives when a trustful relationship has been established. The civil servants and aldermen (City Council Members) involved are then able to overcome formal obstacles, such as mismatch with regulations.