23 Conversation Igniters For Introverts Who Can't Network

Do you know what's the worst? Talking to people you don't know when you are, by nature, ridiculously shy.

Most people who know me superficially do not believe that I have this problem. To them, I offer up Exhibit A: This past Sunday morning, after my mother came to pick my kid up for a day of fun, my husband floated the idea that we go across the street to the local diner, where we know everybody (including the cook/owner), for some breakfast.

I stalled after feeling a moment of panic and finally, when pressed, told him, "I'm sorry, I just wasn't ready to think about leaving the house yet today."

I walk by this diner at least once a week. The people there are perfectly friendly. It is the least threatening place I could possibly go, but the panic!

Truth is, I am painfully shy. But I give a very good impression of someone who is not because it is my job to start conversations with people and discover news in those conversations. (I know, I know — perhaps not the wisest career choice for an introvert — but I'm not the first and I won't be the last.)

The other day I was talking to someone who is also painfully shy and pondered sharing a list of ways I "break the ice" that don't feel totally icky to me as an introvert. She said she'd read it, so you have Mary to thank that it's here.

First: The trick

I have found that introverts typically don't like networking for one big reason: There is a lot of shallow conversation happening, and shallow conversation is draining for introverts.

However, I have found that introverts often enjoy "D&M" (deep and meaningful) talks with strangers. And if you are enjoying the conversation, it's so much easier to forget to be awkward at the other person.

So the trick is to spark a deep connection with your conversation partners. You do this by sharing stories about each other's lives, but not the usual stories about what you do for a living. The goal for the conversation should be for both of you to think to yourselves at some point either "I can't believe I'm about to reveal this about myself," or "I have never told anybody that in my life and I can't believe I just did."

Sound scary? Of course it is, but if you would rather have another dismal round of who-do-we-know-in-common or how-can-we-help-each-other, well, be my guest. I can't stop you, but I can tell you I infinitely prefer to bare my soul than to keep the mask on.

That sounds like the scariest thing in the world to an introvert, and it can be. But it works.

Why it works

People pay attention to novelty. If something is new, we're going to watch it closely — to discern whether it's dangerous or useful.

When you ask someone a question they don't expect, suddenly their brain is telling them to pay attention because something unusual is happening.

So you've got an extra level of engagement right there. Once you have their attention, if you can elicit a personal detail about them and share one about yourself, then you're starting to create something really special — a bond.

And once you've formed that bond, you'd be surprised how often networking talk slides back around to the "how can we help each other" issue — but with a lot more thought and desire to find mutual ground than you'd have if you started off there.

So yes, it's scary. But it's well worth it.

How to go deep

Here are 23 ways to start conversations with strangers, assuming you've been introduced and know this person's name.

Be warned that some of these can veer into political or religious territory. Be careful about asking about scientific mistakes or souls, for example, if you think it could potentially start a fight with your conversational partner. (But the right person will be delighted that you want to know their opinion!)

I'll start with the least threatening/personal — but don't be afraid to ask some of the questions from the bottom of the list. 

  1. What's the best new app you've put on your phone in the past six months?
  2. What's the most interesting thing you learned this week?
  3. If you could put anything you wanted on a billboard on a major highway in your city or town, what would it say?
  4. In which city/state/country did you spend most of your life? What are the best things you remember about it? The worst?
  5. What was your favorite movie when you were five years old? Ten? Fifteen? Twenty?
  6. If you could pick one song as your anthem to start playing whenever you enter a room, what would it be? (You can also ask people to pick a song that they'd consistently nail at karaoke nights, which is a fun one, too.)
  7. What was the best invention prior to 2000? Post-2000? The worst?
  8. What technology did you think we'd have right now when you were a kid that you're still waiting desperately to arrive? (Maybe you can break the news that Hoverboards are a thing! Then talk about whether they live up to expectations.)
  9. If you could pick only one cuisine type to eat for the rest of your life, what would you choose?
  10. Which would you buy first, a robot butler that did all the cleaning (including dishes and laundry) for you in your house or a robot cook that did all the grocery shopping and cooking for you in your house? (You can parse with your conversation partner whether the robot cook also does the dishes.)
  11. Do you think a zombie apocalypse or a robot uprising is more likely as of right now and why?
  12. What's your ultimate "comfort food" meal? What memories does it evoke?
  13. If you could eliminate one word from the language of your choice, what would it be?
  14. If you could wipe one species off the face of the earth, would you do it and which species would you pick? (Uh, mosquitos would be toast if I had this power.)
  15. What job could you not be paid enough to do? What job would you do for free if you didn't have to think about money?
  16. What's a subject that you wish you would have studied — or studied harder — but never did? (What's stopping you now?)
  17. What superpower would you pick if you could pick one?
  18. What do you think is the biggest current scientific misconception?
  19. What do you think has been the most significant social change in your lifetime?
  20. Do you think life exists on other planets? Should we try to find it or leave it alone?
  21. Could we be living in a simulation? What are the ethics of probing and breaking free of the simulation if we accept that it's possible?
  22. How do you feel about attempts to extend the human lifespan?
  23. Are souls real or a metaphysical concept? What do you think they're made of?