Current public lighting is predominately directed to reducing energy and often is understood as a technical issue rather than a human one, mostly based on photometric visual performance. By taking advantage of the inherent flexibility of current lighting technologies, this research aimed to contribute to a more sustainable lighting design practice, through the design of adaptive lighting solutions that improve the relationship between users, the space they inhabit and energy use. To confirm the hypothesis, it was developed a user-oriented method that considers a specific user-space relationship and the user’s perception of well-being. Tested via two outdoor field experiment in an urban space in the south of Portugal, qualitative and quantitative statistical analysis of the collected data, suggest that the method can provide data to aid the design of more tailored and flexible public lighting solutions that can balance the user-energy relationship, improving the overall sustainability of our cities.