Oh just stop with the questions. Asking questions about someone is not a conversation, it’s an interview.
Women are just as bad at this as men. And you are doing yourself no favors with the questions.
You will never get to know someone by asking questions. What you might get is answers to a bunch of superficial questions but that’s it.
My advice slow your role with the personal questions. I get it. You’re trying to get to know someone but people in general absolutely suck at talking about themselves. Asking people lots of questions about themselves is off-putting and uncomfortable particularly for introverts. In my experience that goes nowhere fast. While, you might see it as harmless inquiry and necessary the person you’re asking the question will find it increasingly uncomfortable. Personal questions too early in a relationship put people in a defensive posture. Like someone getting grilled on the witness stand or interrogated by police.
Just stop it. Introverts in particular do not like discussing themselves in this fashion and certainly not until they’ve gotten to know someone very well, but not just introverts. Everyone wants to know someone before they start discussing their most personal details and everyone hates interviews.
Put on your empathy hat, how would you feel if you someone you just met just kept asking you question after question after question. Wouldn’t that be a little exhausting after awhile? I can guarantee at least one of those people you went on a date with got out of there and told someone how annoying you were because you asked so many questions.
Questions do not make a conversation. Save questions for the panel at comic-con not a date.
Instead of trying to lead the person with questions you should shut up and listen more and talk and share more. People will show you slowly over time what they are willing to reveal. Those are areas that you can delve more deeply. But don’t ask questions. Lead with statements, lead with stories. If there is a lull in the conversation don’t fill it with a question. Questions stop conversations more than they start them. If you want to someone to tell you something personal like their opinion on something or their tastes in something, go first. Don’t ask and don’t wait to be asked. Make a statement about yourself and leave it hanging there. It’s the other persons job to pick that up and carry it forward. If you are constantly picking the conversation up and forcefully putting it in their hands, that’s not a conversation.
Questions should be a last resort and ideally only for clarification of the current topic at hand. Instead of a trying to think of the next question, banter, share experiences. “Oh that’s like the time when (I, my friend, my dog) ….” “I remember this time when I (something you did)” Tell a story. That’s the best way and the more self deprecating the better. That then invites the other person to share their own experiences without feeling the need to answer a question.
Mostly however just stop asking questions start telling stories.
