The process of getting to know someone

So I went on a first date the other day. Presumably it was a fairly typical first date - lots of questions about jobs, families, hobbies...that kind of thing. And I started thinking about where the transition starts to happen from getting to know 'about' a person to getting to actually know them. Instead of acquiring facts, you start to get a sense of who they are, their personality, values, what matter to them. These things can't really be deduced via a question and answer session.

Part of what got me thinking about this was that I was comparing the conversation on this date to my conversations with another friend who I've only known about six months or so (I could have chosen any other friend for this comparison process, its just that this particular friendship was the most recent). With the date there were occasional awkward moments where we both racked our brains for another question, whereas with this friend, we never seem to run out of things to say. I was trying to figure out if this should worry me (I decided it shouldn't - it was only a first date after all...but it did send me off on this slightly philosophical rabbit trail).

When this friend and I chat, we are no longer asking each other 'get to know you' questions. Instead we know each other well enough to share the events of our day (we know why something is important to the other person and can commiserate) or simply joke around (we have a sense of what will amuse the other person). So how did we get there? We did start by being part of a social group where we got to see each other in action a bit before starting the one-on-one 'get to know you' process, so that may have helped. But otherwise, I really don't know. I can't recall where that transition might have taken place.

And of course the main reason I'm asking myself all these questions and making these comparisons, is because I want to take the right steps when dating. But how does one go about it? I'm sure a lot of it is just a matter of time. But I feel a certain level of pressure because its a 'date' and not just two people hanging out. There seems like there's a heightened expectation that we are scoping each other out and evaluating suitability - but how do you do that at the 'about' stage before getting to the 'know' stage.

Its a weird conundrum. No answers today...just questions.