I am not shy or introverted when it comes to discussing the majority of topics. However, I tend to dislike questions that relate to my friends and family. I don't like giving out information about someone without their consent.
For example, if a friend asked me what a mutual, but distant, friend was doing for a living nowadays, I would find that awkward. It would strike me that the mutual friend might wish to keep that information private. Especially if I knew it to have an aspect that could be judged - say they were retraining to do a job they loved, but which paid a low salary.
This in itself isn't a problem for me. I'm long used to making judgement calls and swatting away any queries I don't want to answer.
The issue is that I find it very difficult not to apply the same logic when asking questions of other people. Many (most) people enjoy gossip and they especially love to talk about their families. However, I worry a lot that if I ask any kind of personal question, it may be perceived as intrusive and make them uncomfortable.
As a result, it takes me a long time to really get to know people. I'm social enough, but I tend to know almost nothing beyond the surface about those I meet through work or hobby activity. That's not a good thing.
How can I best overcome my fear of being intrusive, and approach conversations with people on more personal questions?
EDIT: I am a native of the UK. Culturally, we have a well-known predication toward being private and reserved. But it doesn't seem to stop people loving to gossip :)