The relationship between interface and content helps to formulate the user experience. The term interface here refers to the way people access systems which in the context of this paper, are not limited to hardware such as mouse and keyboard, or to graphical user interfaces (GUI’s). The interface has a significant effect on how the connection between the user and the content manifests and is traditionally seen as mediating this connection. This paper seeks to explore this relationship in instances where the user has a ‘thick ’ relationship – meaning one with an increased personal or subjective association- to the content. Content (sometimes known as data) is, according to Webster's Revised Unabridged Dictionary, “that which is contained”, in this case by a socio-technical system. In such systems, it is the interface that allows us to access, share, manipulate, generate or communicate with or through it. This paper explores complex content–interface relationships by looking at interactive artworks, commonly designed to be explicitly subjective and personal experiences. In doing so we ask whether use in an art context can inform the development of everyday systems