I ask people questions like:
“If you could invite any person in the world to have dinner with you, who would it be and why? Mine would be Tim Burton because I love his style and artistic approach to movie adaptations.”

or: “If you would have to pick one animal that you feel is similar to you, which one would it be and what characteristics do you think you have in common with them? Mine would be the barn owl, because they are gentle and sweet by nature and rarely get territorial or aggressive.”

Their answers are short, and they usually don’t elaborate, even though I try to set an example with my own answers. Sometimes I have to wait for a few days to get an answer back.
I feel like my questions are more thoughtful than: “H r u?” (I really try to come up with different things every day to shake things up.)

Are my questions too deep..? I like to ask things that make people think, not just: “Favorite color?”/”Favorite food?”/”Favorite activity?”

If I ask something more personal then they tell me that they don’t know me well enough to open up about that (which I understand – trust is built over time).

All the people I’ve talked with have said that they are lonely and want a friend. But honestly.. – it just doesn’t feel like that in most cases where I’ve reached out and attempted to brighten their day while we build something strong and meaningful.

How long should I wait before giving up (seven days, one month..)?
Should I just leave or tell them that I’m leaving (though I’m not sure if they would even care)?
And what are the ways I could improve (asking questions just seems like such a natural way to get to know people)?

TL;DR – I ask people questions (and offer my own answers) to build a bond, but they don’t ask anything back and are never the ones to reach out first. Am I a bad conversationalist/friend, or is it them?

1 comment
  1. I don’t know how well you know these people, but the questions that you mention sound like what I’d expect to be forced to answer in some sort of professional development seminar. They are faux-deep, a little out of the blue in casual conversation, and sound insincere.

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