Intergenerational interaction can promote positive experience for both grandparents and grandchildren. However, sustaining such interaction can be difficult due to geographical separation, lack of common topics to talk about, etc. In this work, I 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. First, I conducted an environmental scan of video conferencing and music listening platforms and technology configurations feasibility to investigate how these platforms can support collaborative music listening and conversation between a grandparent and teen grandchild. Second, I conducted a qualitative study where I recruited grandparent and teen grandchild dyads to co-listen to favourite songs and have conversation about them. In the qualitative study, I conducted a technology probe via a ‘Private DJ’ mechanism that facilitated music streaming within a video conference. I found that the inclusion of music as a conversation catalyst provided a ‘Ticket-to-Talk’ between the dyads (6 dyads, 12 participants), alleviating conversational awkwardness and supporting peripheral quality interactions. By providing avenues for technology development to make it easier for separated family members to have meaningful and sustained communications, results of my work support the ongoing design of online family communication technologies to include increased support for co-activities such as music co-listening.