Good morning, Lovebug! It's taken me many years to learn the lesson I want to teach you today, and I'm still working on it.
But there's a better question to ask, and learning how - and when - to ask that question is an art that takes a lifetime to master.
Becoming more like Christ means looking at how he relates to people. He cares, deeply cares, about every aspect of their life. Allowing Him to show His care through your life is a powerful ministry both to them and you. This isn't "Conversation 101", but rather another aspect of growing in grace.
Instead of asking "How are you?" ask a question that demonstrates your interest in their daily life.
Ask a question that can be answered in a word or two but leaves room for them to share more if they would like to.
They may not have the time or the desire to talk about the topic you bring up. But more often than not, people open right up when someone takes the time to ask them a personal question.
Ask a question that has a straight, factual answer.
Casual encounters in public aren't the time to drag emotions and feelings into a conversation. Very often people's emotional reactions to an event are ambivalent or the opposite of what you would expect. I would twenty times rather hear "How are you?" knowing the person doesn't really care than have them probing my thoughts and feelings during a casual encounter.
Consider the context of your relationship.
Keep your questions focused around an item that is common knowledge about that person or something they have directly told you.
Consider the surroundings.
Most of the time it is not appropriate to ask about anything personal in public, especially if other people are within earshot.
Vary the question.
People aren't one-dimensional. You've only exchanged one meaningless question for another if you ask them the same different question every time you see them.
Keep it positive.
When a friend is facing a major life event like unemployment, illness, or a death in the family, it's on their mind 24/7. You have a couple of choices. You can mention that you've been praying and ask a question that doesn't carry a lot of emotional weight, or you can simply ask them something about an area that's positive in their life.
Even simple questions often open floodgates. When people say something out loud, they often begin self-counseling. Let them talk. If they make silly assertions about or accusations against God, gently re-direct their thinking with questions.
Two cautions if you are chosen to listen to another's heart: Unless directly asked, don't share an anecdote from your own life in an attempt to display empathy and don't prattle off unsolicited advice after a 5 minute conversation.
If someone entrusts you with their heart, take the time to follow up via e-mail, a phone call, or even a note dropped in the mail. Pray for them. If the person is in distress, make time for a personal visit. Under no circumstances say "Give me a call if you need anything." They won't. You need to follow through.
The most important thing? Keep it genuine. The goal isn't brilliant conversation but rather to demonstrate Christ's loving care for people through your heart and life.
Love to talk with you!