In order to build an intelligent system that allows human beings to cooperate with a computing machine to perform a given task it is important to account for the individual characteristics of each user. In this work, we describe a flexible and adaptive user interface that is capable of interpreting spatial linguistic expressions according to the peculiar preferences and use of language of the user. As a proof of concept, we have implemented a graphics board game in which players can move, remove and spatially manipulate in 2D various game pieces on the computer screen by issuing speech commands during a dialogue session with the application. After an initial guided interaction, the system analyzes on the fly subjective interpretations of several linguistic relationships that form the basis for spatial expressions to tune a set of system’s parameters. We tested the system with different human subjects. Automatic judgment of spatial expressions based on each user’s interaction behavior over-performed sentence interpretation of a model that we previously created to tailor the characteristics of some abstract typical player. Post interaction informal talks also indicated a higher level of user satisfaction in subjects playing with the customized application rather than the more general one.