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Vika comments on How to have high-value conversations - Less Wrong Discussion
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Thanks for the great links! I agree that getting people to feel comfortable is really important for having good conversations. The list of questions in my post is intended to find personal topics that would be of common interest, but I think it's much more likely to work if the people involved are already feeling comfortable with each other.
Your CouchSurfing experience reminds me of a class at Burning Man where people were split up into pairs, and tried to take the shortest conversational path to getting to know each other. There was a built-in affordance to ask personal questions about feelings though, since everyone was in the class with that purpose. Did you end up developing patterned ways to ask strangers about they thought and felt without it feeling awkward?
It didn't feel awkward, probably because my approach was sufficiently coarse-grained: I didn't rely on any specific "lines" or "routines" to artificially generate closeness, but only on the general principle that the conversations should become progressively more personal and intimate.
I wish I could remind myself of the value of this principle more often, however. I often end up having superficial interactions with people I'd like to know better simply because that's the default way I relate to others. Recently, I started experimenting with Anki, using one side of the card to describe the relevant situation (e.g. "I find myself in the company of someone I'd like to get to know better"), and the other side to describe what I should do in that situation ("I ask questions that are progressively more personal and intimate").