19 Questions to Help Shy People Make Conversation

#2: Who is your favorite superhero?

Matthew Kent
6 min readSep 22, 2020


Photo by Julian Hochgesang on Unsplash

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:


What do you most like to do for fun?

We always ask people about work, but how they play is just as important to who they are.

Who is your favorite superhero (and why)?

This is a silly change up to throw in to keep the conversation lighthearted. That said, it can actually start some pretty interesting conversation.

This is a question that keeps working well even as you add more people into the conversation.

A really fun variant: who is your favorite Disney princess (and why)?

Is there a charitable cause you support?

This one can be a bit tricky in terms of tact; if they don’t give money to charity they might be uncomfortable with the question. Of course, you can make it clear that the definition of “support” is broader than financial giving.



Matthew Kent

Done settling for average. Now I have my sights set on awesome 😎 Get “The Ultimate Daily Checklist,” my free ebook on productivity: http://bit.ly/2pTziwr