17 questions for sparking fascinating small talk, from a psychologist

When I was younger, I used to joke that I had an STD called Small Talk Disorder. I’d be flummoxed, tongue-tied, checking myself, and then leaving the encounter replaying it in my head. Going through it with an unnecessarily fine-toothed comb and beating myself up, before dreading the next encounter.

While my 30-something-year-old self now understands why this played out on multiple levels—my ADHD brain abhors the sluggishness of boring conversations, my introverted wiring hates meaningless speech that revolves solely around the weather, and my previously socially anxious self had invisible meltdowns every time she socialized—my younger self felt clueless and cursed.

 Maybe you share some or all of the above qualities that contributed to my hatred for small talk. Or maybe you’re an extrovert and feel that way too because extroverts are not immune to feeling socially anxious.

When I trained as a clinical psychologist, one of my first vows to myself was to walk my talk, the first step of which was to tackle the social anxiety that no one knew about. I stared at the problem from multiple angles, and then I took bestselling author Ramit Sethi’s Mental Mastery course, where he likened small talk to part of the rituals of life. He said you don’t go to a fancy restaurant, gobble your food, and rush out. As a self-confessed glutton, that, my brain could get. And so I learned to stomach small talk—I didn’t like it, but every house has a dustbin.

Then I asked myself, what if small talk was so fascinating that even introverts and people with ADHD would engage heartily in it? Enter, my favorite questions I’ve collected over the years.

A list of questions for engaging small talk

Here are some of my favorite questions for engaging small talk. They pull inspiration from some of the many tried-and-true conversation starter collections, from the legendary parlor game Proust Questionnaire to love experts Aron and Aron’s 36 questions to fall in love, to author Alexandra Franzen’s 100 Questions To Spark Conversation and Connection. The full list is featured in my book This Is What Matters.

Light questions:

  • What’s the best thing that happened to you today?
  • What made you show up today?
  • What would you like to get out of this [event] today?
  • Easy questions about the other person:
  • Do you identify as an introvert, extrovert, or ambivert?
  • How would your best friend introduce you to a stranger?
  • How do you spend your days?
  • Are you a coffee, tea, or chocolate person?

Interesting questions that make people think:

  • If you could invite anyone living or dead to a dinner party, which three guests would you invite? And why?
  • What’s your favorite journey you’ve ever taken? And why?
  • Everyone has aspirations apart from the big life goals that I call Dubious Life Goals. They may be funny, warped, or tiny. Do you have any?
  • Tell me a secret thought you’ve been having all day.

Questions to cultivate deeper intimacy:

  • What is your idea of perfect happiness?
  • When was the last time you astonished yourself?
  • If you could sit down with your 13-year-old self, what would you tell them?
  • If you could choose your life obstacles, would you keep the ones you have?
  • What are you most grateful for right now?
  • If you were a perfume, what scents would you be made of?

The takeaway

Most small talk revolves around the weather, “How did you get here?” or “What’s your job?” There’s only so much you can talk about with the first two, and they don’t work on everyone. Asking different questions can subvert the expected, pique curiosity, and help both parties learn to listen more deeply to each other. This forges a sense of connection and intimacy, without the risk of eroding someone else’s boundaries or giving too much information.

As an exercise in self-awareness that might bring you a few hearty laughs, consider your own responses to these questions. And if you are a question geek like me, you may have fun crafting questions that suit your style more.

Understandably, it may feel strange asking these questions initially. Start with the lightest ones, and then use the others in response to a conversational tidbit that the other party offers.

Most importantly, remember that the people who make their craft look effortless have practised for thousands of hours. So, use each opportunity to refine the art of having fascinating conversations. And reap the rewards that come from deeper connections.