Ask questions. Lots of questions. Especially open-ended ones. Hopefully the other person opens up and you can have a deeper conversation. This usually works for me. I tend not to talk about myself and my point of view but instead I show the other person that I am interested in what they have to say. This usually makes them feel more at ease and my inquisitive nature is rewarded.

One of the best conversations I’ve had was about fear and overcoming it in face of hostile environment (e.g mountaineering) Getting to the root of what makes another person tick was fascinating. Talking around a fire seems to be conducive the great conversations. There is something about fire which is calming, soothing and makes people feel comfortable and at ease.

Good luck!