Robots and digital agents find their way in an increasing number of areas in our everyday lives. In this paper we look at the history of coaching devices and their impact on our health and lifestyle, as well as the emergence of coaching robots. We explore the worry that a growing entanglement with coaching technology that quantify our lives may reduce or invalidate the user’s personal experiences and preferences. We propose that the kind of bond that should be formed between user and technology is one that engenders trust while maintaining contextual and user-focused perspectives, in order to preserve personal values and autonomy, as well as the possibility of coaching robots being able to provide these kinds of bonding interactions.