Well-being apps promise to improve people's lives. Yet evidence shows that the data-hungry app culture that contextualizes well-being apps normalizes the user experience of affective discomfort. This apparent contradiction raises a difficult question: Is it responsible to ask people to improve their well-being by engaging further with an app culture that normalizes affective discomfort? We approached this question by deploying an online, scenario-based survey (n=688) about a fictional, but realistic well-being app called "Thalia." Thalia represents a novel class of well-being apps that are envisioned to: (i) utilize AI-driven facial recognition and analysis; and (ii) collect data for use in medical contexts. We found that people perceived Thalia to be affectively discomfiting even as they judged Thalia to be beneficial. Such findings imply a trade-off between 'better living through technology' and the negative affective implications of surveillance capitalistic app culture. Such a trade-off necessitates high-level analysis of just what "well-being" means in the context of contemporary app culture. Through analysis and discussion, we explore a troubling interplay between novel well-being apps and affective discomfort that requires careful attention from HCI researchers if human-centered well-being -- flourishing -- is truly what our products are intended to foster.