How does one move from pleasantries and small talk to interesting conversations with depth and significance?

Haha know just what you mean. Trouble is that while we might find depth and significance in our conversations others may find them offensive and troubling.  So you have to sort of test the waters.  I have been criticized for being to earnest on this and other chat sites when most people it seems just want to make light and fool around. So have learned not to expect more except with certain people. On answerbag we had more participants so there were few topics we could not enroll a group of people in conversing fairly seriously about. But we must face it - I know most people care not at all to hear about anything I think about or my feelings most of the time.  They have their own lives to lead. I am happy just to have a husband and a few close friends who enjoy deeper conversations with me. More as I get older I confine myself to my husband for conversation as we are best friends. When he is not working which is most of the time (that he is working!).

Are you from Oz? Aren't Aussies pretty laid back and easy going? I'm lucky, I'm interested in people. It make conversation easier from my point of view. There are lots of people from elsewhere where I live. I am always saying 'D'you mind if I ask where your family is from'. So often the answer is something I don't expect. People are most often happy to share that kind of personal  information rather than offended by the intrusion - in fact, that has never happened to me.
An extreme case of this enquiry was at a restaurant in Wokingham in Berkshire. The serving girl had a slightly swarth look which left a very open field for speculation (I like to guess). She also had an accent that, despite my interest in, and facility with, accents, I couldn't place, but it was vaguely French. Intrigued was the word. When I asked the question the answer came as a shock - she was from Mauritius. So a young girl from Mauritius had somehow found her was to, of all places, little-known and insignificant Wokingham, that a few years before I had never even heard of. 
If I find myself in one-on-one conversation with someone I'm really uncomfortable with, I take that as a sign, and break off. Some people seem either to not care or not notice about the dark aspect of other people, but I think that, like a sensitive dog, I know which are the 'good' people, and who it is best to stay away from. It probably makes no difference to them anyway. Just one opinion of course. 
  

 

  Are you referring to conversation in general, or specifically one-one-one live conversation, or specifically online conversation?
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Those types of conversations take place in person. 

 

  For me, slipping into something more comfortable is often a great transition to achieve that goal (cough, cough).

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