High levels of stress during pregnancy increase the chances of having a premature or lowbirthweight baby. Perceived self-reported stress does not often capture or align with the physiological and behavioral response. But what if there was a self-report measure that could better capture the physiological response? Current perceived stress self-report assessments require users to answer multi-item scales at different time points of the day. Reducing it to one question, using microinteraction-based ecological momentary assessment (micro-EMA, collecting a single in situ self-report to assess behaviors) allows us to identify smaller or more subtle changes in physiology. It also allows for more frequent responses to capture perceived stress while at the same time reducing burden on the participant. We propose a framework for selecting the optimal micro-EMA that combines unbiased feature selection and unsupervised Agglomerative clustering. We test our framework in 18 women performing 16 activities in-lab wearing a Biostamp, a NeuLog, and a Polar chest strap. We validated our results in 17 pregnant women in real-world settings. Our framework shows that the question "How worried were you?" results in the highest accuracy when using a physiological model. Our results provide further in-depth exposure to the challenges of evaluating stress models in real-world situations. 1 INTRODUCTION While immediate short-term mental and physical stress can be beneficial to health, prolonged elevated stress levels negatively affect the body's respiratory, cardiovascular, digestive, muscular, reproductive, nervous, and immune systems [18, 50, 54]. Prolonged stress can also contribute to poor health behaviors such as overeating [45], smoking [34], alcohol [42] and substance abuse [46]. These behaviors, in turn, are associated with conditions such as hypertension, heart disease, and depression [8]. Indeed, stress exposure in utero has been linked to deleterious outcomes for the child including impaired motor development, lower mental development, heightened behavioral disinhibition, and associated