Background: Meaningful intergenerational interaction can help older adults view aging more positively, provide a means to pass on their cultural identity, and support general well-being. However, maintaining intergenerational relationships may be difficult due to geographical separation, lack of common conversation topics, scheduling challenges, and recently, pandemic-related restrictions. We explored music co-listening over a typical video-conferencing platform to see how such platforms can support a rich and sustained connectedness between grandparents and teen grandchildren. Objective: In this research, we explored the following questions: What interaction and conversation patterns happen when older adults and grandchildren share their music with each other over a synchronous video conferencing tool? What types of intergenerational interactions around music co-listening online should communications technology support, in order to support inter-generational conversation? Method: We conducted a qualitative study where a grandparent and teen grandchild colistened to favourite songs and had a conversation about them. Results: From this exploratory study, we found that the inclusion of music provided a 'Ticket-to-Talk' between our dyads (6 dyads, 12 participants) by supporting peripheral quality interaction with mu-sic. Our 'Private DJ' mechanism simplified the process of colistening to music online and conversing around it for the dyads. The planning of songs to share, anticipating the other party's song selections, watching the partner's song selection, and having time between the songs to have a conversation, all seemed to contribute to making the synchronous intergenerational communication enjoyable between our dyads. Conclusion: Our results support the ongoing design of online family communication technologies to include increased support for co-activities such as music co-listening, to make it easier for separated family members to have meaningful and sustained communications.