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The aim of this research is to conduct a pilot study of a prototype that provides feedback using theory-based motivating messages developed by older adults, in a context of every day activities that include both physical and social activities. The prototype mobile application integrated the messages, a motivational model, and a personalization module that selects motivational messages based on preferences, motivational profile and the situation. The four participating older adults used the application for planning and following up social and physical activities. They found the messages entertaining and appreciated the dialogues with the application. They used the dialogues primarily to reinforce their satisfaction regarding conducted activities and did not necessarily tell the truth about conduced activities in the interaction with the application. The results are preliminary, but give valuable implications for further development of the personalisation module towards more purposeful use of ambient information, and aspects to explore in future user studies.