When getting to know people, it is natural to ask questions about their business and personal lives. In order to build long term relationships with people, you need to know something about their personal lives. Knowing about people beyond business is healthy for the relationship.
The more and more you interact with people, the more comfortable you feel. When this happens, you will begin to ask more personal questions. Be careful that you don't cross any uncomfortable boundaries when asking certain questions.
You know your relationships the best so you should be able to know when you should stop asking questions. Show respect and courtesy by not asking inappropriate questions.
However, there are times when you don't know if you over stepped your boundaries until the person says something to you. At the same time, you may think that you went to far when in reality the person didn't get offended.
This is what happened to me over the weekend while playing golf. I was playing my third round with a person who I met last year. Every time that we play, we get to know each other better. So, I opened my big mouth and started asking some more personal questions. He told me that he had 4 kids but because the oldest and youngest had such a big age gap, I acknowledged this difference.
He explained to me that his wife died giving birth to their third child. Then, he re-married and thought that he had a son with this woman but found out later that she had an affair and that the child was not his. I felt bad for prying but he handled it well and said that it was okay to talk about because it happened a long time ago.
The lesson that I learned was not to ask too many questions that may make someone uncomfortable, which could include me. Have you had any experiences where you asked too many questions, which resulted in an awkward moment?