As online education expands, cultivating a sense of belonging becomes increasingly complex, especially for students who may never set foot on a physical campus. In this article, we explore the nuanced nature of fostering a sense of belonging and mattering among distance learners on our own campus, Indiana University (IU) East. To address these students' unique needs, our English department organized three virtual events (the Alumni Career panel, the Faculty+Student Reading of creative work and the Celebration of Student Writing) utilizing Facebook Live, Zoom, and Pressbooks. Drawing on the concept of "belonging" as articulated by Strayhorn (2019), we examine the degree to which these virtual events fostered a sense of belonging and mattering, particularly through the concept of "matched pairs," which emerged as a useful framework for creating personalized connections between faculty and students, a critical ingredient in both belonging and mattering. Both the Faculty+Student Reading and the Celebration of Student Writing worked to establish closer ties between participating faculty and student pairs, while the third event, the Alumni Career Panel, encouraged students to interact with alumni in a virtual "living room," a relaxed online space (via Zoom) where they could learn about career paths. However, we also found that events like these cannot be viewed as "one-and-done" but rather must be part of a sustained program to enhance student connections. Acknowledging the time-intensive nature of planning and organizing such events, we caution against assumptions of seamless execution and underscore the need for purposeful planning, inclusive design, and flexibility to accommodate diverse student needs.