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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 :)

7

Think of topics of conversation as different layers. The top layer is small talk: superficial stuff like the weather or sports. As you go deeper, it gets more and more personal. You have to dig through the first layers before you get to the very personal stuff - people typically react poorly if you try to skip straight to "So, how's your relationship with your father"! It's a process to get to know people.

Things you can do:

  • Ask open-ended questions
    Open-ended questions, like "How was your weekend?" gives the recipient plenty of discretion on how much they want to share. They could say "It was really interesting, I went on a blind date", or they could say "Oh, nothing much going on, how about you?"

  • Recognize invitations to ask questions
    When an acquaintance hints at something personal, without going into details, they may be testing the waters to see if you want to talk about it. (I do this when I'm not sure if the other person is interested in my personal life - if they don't inquire further, I don't feel foolish for over-sharing, and if they do I feel "safe" and that they actually care.) This is more likely when you've asked them an open-ended question. In the above example, the blind-date-haver might be hoping you'll follow up. "Really! How do you mean, 'interesting?' Who set you up?"

  • Open up about your own life
    It's all about building trust in the relationship. If you're willing to share personal stuff with them, they will feel more comfortable sharing personal stuff back. Again, I am often on the other side of this thanks to social anxiety. For example, with a new person, I might worry that it's out of place to mention my boyfriend. But if they start waxing poetic about their partner, that signals to me it's an acceptable topic of conversation with them. This is also common with touchy subjects like politics - both parties are afraid to mention it, but once one breaks the ice (in a respectful way!) there is a sense of relief, and we can talk about it freely. Level up! (er, down? mixed metaphors are hard..)

  • Display genuine caring for their personal life
    This is the most important one! Learning more about someone's life is a natural consequence of caring about them, so questions won't seem out of place. Plus, most people love to talk about themselves and will be happy someone wants to listen.

After they have shared things with you, follow up. This lets them know the information wasn't "wasted" and shows you are still interested. For example, if a coworker mentioned visiting her parents for the weekend, you could ask if they went to any fun events together. Or if that still feels too personal, you could ask how the drive was. This gives her an opportunity to share more, or just as easily say "Oh, it was fine" and not go into detail.

Start off slow and pay attention to people's reactions. If they start responding with short, non-committal answers or look uncomfortable, back off and apologize if warranted. "Sorry, I didn't mean to intrude! Back to the potluck - where did you get that recipe for potato salad?" This lets them know you recognize their boundaries, and are happy to continue a friendly conversation within those bounds.

2

The first thing to remember is that how you approach a subject will depend entirely on the person. People who are willing to share their personal information will do so quite easily with a probing question such as 'Oh and why did that happen?' or 'How is it going with [insert boyfriend's name etc.]'?

Other people will be less willing but before I go into how to approach that, I wanted to comment that it seems you are putting a lot of pressure on yourself in these situations which probably makes you feel more uncomforatble. It might help you relax if you stop and think that these people are just like you and they will deflect any questions they do not want to answer. Once you've asked something and someone deflects it, take that as your cue to avoid that subject (only approach it again if your relationship deepens). People in general will not be annoyed if you ask a question, they will only be annoyed if you ignore their dismissal.

As for people who do not openly speak about themselves (but not necessarily are avoiding the topic - maybe they are just shy), it comes down to asking more questions.

For example, say I have an aquintance called Lee who is very outgoing, all I might have to say to him is,

'Hey Lee, still loved up?" And I will get the whole story of the great romance and the break up and the new love interest.

However I might then approach a friend called Joanne who is quiet and it might take me many questions to get the details eg. '"Hey Joanne, still loved up?"

Joanne: "No, not anymore."

Me: "Oh that sucks, you okay?"

Joanne: "Yeah I'm fine."

Me: "Are you guys still going out? What happened?" etc etc.

If Joanne doesn't want to talk about it she'll give signals such as changing the subject or not answering. Otherwise if she keeps answering she is probably okay with talking about it, just shy about talking about herself. If you can I would also suggest injecting snippets about your own experiences into the conversation as people will find it easier to connect with you and let their guard down. eg.

Joanne: "We broke up because he wanted to move to Canada."

Me: "Oh I'm sorry to hear that, I had an ex who moved to New Zealand and we tried to make it work but it didn't, it really sucks. Why is he moving, did he get a new job?" etc.

Getting to know people can be really quick or really slow depending on the person but as long as you stay interested in them and show you are willing to listen and respond, your relationships should get to a deeper level.

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