When I meet someone new who seems interesting, I tend to ask him or her a lot of questions. My attitude is, I already know about myself and I know nothing about this person, so why not try to learn more about the unknown?
If someone tells me she flew somewhere, I ask what airport she flew out of, about her flight route, her experience on the plane, how she bought her tickets.
If someone pulls out a credit card to pay for a meal, I ask about the card, the point system associated with it, why he chose it, how he tracks expenses, where he banks, etc.
If someone asks me what books I’m reading, I’ll answer quickly, and then ask him what books he’s reading, whether he buys or rents books, whether he takes notes or scribbles in margins, whether he reads fiction, how he decides what to read, etc.
Here’s the problem: it can make people uncomfortable. Once a friend took me aside and said, "Ben, you’re, like, interrogating the guy."
Here’s how I’m dealing with it: if I feel like the conversation is too one-way, I say something like, "I’m not trying to play 20 questions, I’m just really interested." This tells the other person that I’m aware of what’s going on and am, in fact, genuinely interested, not interviewing her for a police report. Even a simple one-liner of this sort lubricates the social interaction in a helpful way.
Aren’t you more accepting of someone who says, "Sorry I’m a backseat driver!" before or during her criticism of your driving skills? Or more accepting of a long-winded person who at least acknowledges his tendency to be verbose? This principle applies in various situations.
Bottom Line: Showing an ounce of self-awareness around potentially annoying / intimidating behavior goes a long way to making people comfortable with it.