This works in conversation, too. There's something powerful about the experience of diving down to meet someone in the low place they're sitting in, while keeping a bit of yourself apart as a lifeline - you can sync up with them by observing and validating the way the world looks to them from that hurt or scared place, then, step by step, help bring them closer to the surface by suggesting a little bit of a broader view at each turn in the conversation.
But yes: you really do have to have some time to kill, and it can be tricky to set up an environment in which a sustained, unpressured conversation can occur.
(What you are describing with your playlists sounds like the soul of DJing. Perhaps you might try playing with a controller sometime, if you haven't done so already.)