I went to a conversation dinner thing the other day. It's based on the teachings of Theodore Zeldin, a philosopher and historian who wrote An Intimate History of Humanity. He thinks people don't talk to each other enough about deep personal things so he set up these dinners where you meet strangers and ask intimate questions.
I'm really glad I went, I enjoyed it a lot. I reminds me a lot of teaching english as a foreign language. You have to ask personal questions all the time to get students to use the grammar. E.g. "What games did you use to play when you were younger?" Or " What do you wish you had done differently?"
Article about Theodore Zeldin and the conversation dinners by Lloyd Davis
It would be a great way to make new friends if you move to a new place.
Although I enjoyed the experience a lot I think it would only work for certain kinds of introspective, perhaps a bit neurotic, articulate types (like characters from Woody Allen movies.)