We have created a system for data collection, annotation, and feedback that is part of a longer-term research interest to gather data to understand more about stress and the physiological signals involved in its expression. First, we built a wearable apparatus for gathering data that allows the user to include as many accurate labels (annotations) as possible while going about natural daily activities. Gathering annotations is disruptive and likely to increase stress (thus interfering with the signals being measured). We hypothesized that empathetic ways of interrupting would be less stressful than non-empathetic and found significant effects on many of user's self-reported items such as preference for the more empathetic system, and also on behavioral items, such as the estimated number of times they were interrupted (significantly lower when system was more empathetic.)