As focus in the interaction design community continues to move beyond the office, a key challenge for researchers and practitioners interested in designing pleasurable products and experiences is developing a sensibility for understanding the real and situated complexity of everyday life. Human- computer interaction, as it owes to the traditions of cognitive science and engineering, has been effective at producing mental and behavioral models to inform design for the workplace; nonetheless these approaches are less helpful when applied to everyday contexts, such as the home, to inspire the design of engaging experiences. In this paper we describe the methods and process of a design-oriented approach to ‘multi-dimensional’ user research we conducted to better understand the nuances of elderly families' everyday lives. We conclude with a brief reflection on this type of approach and why it is important in the context of designing pleasurable interactive products.