Our study aims to explore the affordances of conducting research with an online choir for older adults and to examine how participant-observer experiences can inform our practices as performing musicians, music educators, and researchers. Studies show that participating in music and dance classes facilitates creativity, community, belonging, and enjoyment (Creech et al., 2013). Similarly, music enhances self-identity and reminiscing (McCabe, Greasley-Adams, & Goodson, 2013), while improvisational dance can foster a sense of expanded time and space (Almqvist, 2020). However, not enough is known about music theatre in a virtual platform and the role of participant-observers within this setting. To fill this research gap, we used a Collaborative Scholarly Personal Narrative methodology (Nash & Viray, 2013; Nash, 2019) as a means of interrogating our shared experiences as researchers on Rise, Shine, Sing, a weekly, Kingston-based virtual music theatre program of approximately 20–30 participants. Drawing on observation reports collected over five months, we reflected upon participants’ levels and patterns of engagement, the choice of repertoire, and possible areas for improvement. We also reflected upon the advantages and disadvantages of conducting sessions online as opposed to in-person. Through a process of individual and shared inquiry, our findings revealed that building a sense of community led to increased engagement, with participants becoming more comfortable sharing their talents and conversing with others. Furthermore, our experiences with this online community of researchers and participants allowed for new forms of engagement and programming which will likely benefit our professional practices in significant and exciting ways.