Listen to what your friend keeps almost saying. That’s usually the real conversation.

People circle what matters before they say it. A subject gets brought up and dropped, then brought up again from a different angle as a joke, and the circling is the signal; nobody keeps returning to something they do not need to talk about. The real conversation is the one being approached, not the one being had.

If somebody keeps edging toward a thing, your job is mostly to leave room. Stop filling the pause, or say gently that it sounds like there is more to it, and then wait. If they change the subject, let them, and they will usually come back to it another day.