This thesis presents the results of the project “Creating meaningful conversations user-data”. This project aims to understand the impact that interactions with technology currently have on users and to redesign a fitness tracker service to create more personal and meaningful experiences. These experiences enable fostering the users’ wellbeing and ultimately user engagement. The project explores the personality (conceptual characteristics) of the fitness tracker and its impact on user interaction. Moreover, it researches the meaning and value of health for the individual. These trackers are perceived by the users as very controlling in the interactions, which are mainly based on outputs and behavioral instructions leaving the user a passive role on the experience (conversation). The reason is that trackers follow a machine personality approach based on optimization and goal-seeking. Moreover, it has been found that the value of health for the tracker follows a different approach than the user. While the user values health to find balance and self-care based on doing holistic and meaningful activities, the trackers approach health as a predefined list of activities and are based on performing and achieving. This tracker approach zooms in on the activity (tangible meaning), difficulting for the user to see beyond and find the personal meaning that these devices can have to transform their lives (intangible meaning) into a healthier life. To design a more meaningful conversation user-tracker, five specific challenge areas related to this problem have been found: meaningless and impersonal goals, trainer tone of voice, linear and achievement focus, perceived lack of self-control and lack of health balance. The redesign is a new concept for the fitness tracker service (mobile and smartwatch app). It tackles the entire concept of the fitness tracker service (mobile and smartwatch app), rather than only data visualization because there needs to be a common ground regarding the personality of the user and the tracker (such as having a common approach to health) before the user-data conversations can become meaningful. The redesign zooms out from tangible activities and frame goals as journeys towards a healthier life. In this journey, the user is not only supported in the achievements but also empowered in the lower points of the process though self-reflective questions to learn from his unconscious behavior, which makes the service a platform for self-growth and gives the user a proactive voice in the conversations user-tracker. Moreover, a meaningful topic of conversation is established from the beginning of the experience by the “goal-setting” where the user can define holistic and personally meaningful goals to design his future-self. Finally, the motivation strategy of the app has been shifted from competition and achievement to share learnings with others (Self refections) regarding the journey, since it has been found that in this context, motivation related to de creativity. Therefore the user finds meaningful the experiences that inspire their behavior rather than instruct it.