I think my biggest issue is actually caring about the other person enough to ask those questions. I know that sounds a lot worse that it probably really is, but these days, you run the risk of finding someone who wants to share their entire life story with you. Which if it was interesting, it might not be a bad thing, but it's mostly just trailer trash drama most of the time. Trust me, I know how that sounds. It's just hard to open that door when it generally takes something pretty significant to actually hold my attention.
I don't see the problem in that approach. With so many disconnected and lonely people now, there are many willing to jump on the chance to talk about their little lives, making mountains from molehills.
My wife and I went out to breakfast a couple weekends ago. We paid our check and when the waitress brought back our receipt she went on a ten minute long story about her Christmas tree she bought on Amazon. What can you do but smile and nod at that point... We just wanted to pay and get out of there!