Digital services face a fundamental trade-off in content selection: they must balance the immediate revenue gained from high-reward content against the long-term benefits of maintaining user engagement. Traditional multi-armed bandit models assume that users remain perpetually engaged, failing to capture the possibility that users may disengage when dissatisfied, thereby reducing future revenue potential. In this work, we introduce a model for the content selection problem that explicitly accounts for variable user engagement and disengagement. In our framework, content that maximizes immediate reward is not necessarily optimal in terms of fostering sustained user engagement. Our contributions are twofold. First, we develop computational and statistical methods for offline optimization and online learning of content selection policies. For users whose engagement patterns are defined by $k$ distinct levels, we design a dynamic programming algorithm that computes the exact optimal policy in $O(k^2)$ time. Moreover, we derive no-regret learning guarantees for an online learning setting in which the platform serves a series of users with unknown and potentially adversarial engagement patterns. Second, we introduce the concept of modified demand elasticity which captures how small changes in a user's overall satisfaction affect the platform's ability to secure long-term revenue. This notion generalizes classical demand elasticity by incorporating the dynamics of user re-engagement, thereby revealing key insights into the interplay between engagement and revenue. Notably, our analysis uncovers a counterintuitive phenomenon: although higher friction (i.e., a reduced likelihood of re-engagement) typically lowers overall revenue, it can simultaneously lead to higher user engagement under optimal content selection policies.