Do you have any friends that are a bit “private”? Maybe they aren’t really averse to letting you know something about themselves. They just aren’t used to opening up spontaneously. So when you ask “how are you?” You know you’re going to get the usual response from them. “Fine thanks”

Why not ask specific questions. Something like “how is Jack doing in his new job? Are things any easier for him now?” Now the other person knows what you’re interested in finding out and can respond with a deeper answer.

This takes time. It even took me time to think of a more specific question as an example. But by taking that time I had to decide what I really wanted to know about Jack. Maybe I wanted to know if my friend and Jack were still fighting a lot like they were when Jack was unhappy in his job. Her answer to this question about Jack’s new job might afford her the opportunity to follow on with more info. And she doesn’t, her response and tone of voice might give me a clue as to whether I should probe deeper or just leave that subject alone for the time being.

When you buy something you really want to know more than “what does it cost?” But if you don’t know what matters, then you might end up with a “lemon”. I did. A long long long time ago I was at a car dealer and I saw this convertible that I wanted. All I asked was “how much?” And boy was I sorry. It was the absolute definition of a lemon. But i learned a lot from that experience.

It’s a bit of work but if you are a curious person, it’s well worth it. Figure out what you want to know and then come up with better questions that will help you get there.