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19 Questions to Help Shy People Make Conversation
#2: Who is your favorite superhero?
As a shy introvert, I’ll tell you that meeting new people is exhausting. So is making conversation with someone I don’t know well.
It becomes even worse when I have to fall back on a cliche like “so…what do you do for a living?” I can’t help but think that the use of such a crutch reveals my ineptitude at connecting with other human beings.
Late last year I decided to enter these kinds of conversations prepared. I researched various lists of questions and came up with the 20 I thought were best (including a few I invented myself).
I wrote these in the beginning of my journal to reference when needed. Whenever I’m going into a situation where I’ll probably talk to someone I don’t know, I review the list and pick two or three to use.
Some of the questions are intentionally silly or shallow, and some are actually quite deep. Some are good for breaking the ice, and some are best for taking things a little deeper.
They work just as well over zoom as they do in person.
Here they are, organized by category:
