20 Questions to Spark More Memorable Conversations

good conversationalist is like a good editor, helping the speaker center in on what's unique, insightful, and meaningful about themselves.

Think about the best conversations you've had in the last few weeks. Chances are, they were about surprising topics where you learned something new, either about your conversational partner or about the world.‍

For the past few years, I've been compiling a list of questions that spark those kind of learning moments. I use it in three ways:

1. Before Dinners/Parties: In the cab on the way to see people, I'll quickly review the list. If a chance presents itself during the night to organically ask a question, it'll be fresh in my mind. Of course, I never go with the intent of forcing a question, and only sometimes do I end up getting to use one of the below questions, but when the moment presents itself it can be a bit like magic.

1. Meeting New People: If I know I'm about to meet new people, I'll review the list. I've found the questions below are excellent as a way to get to know people quickly and deeply while also leaving them with a positive impression.

1. With Close Friends: On more than one occasion, in the wee hours of the night, I'll open up the list and go through each question, one by one, with the friends I'm with. Usually we'll get through 3-8 questions over the course of the hours, since each sparks a deeper conversation. This has a 100% success rate and has led to some of my favorite conversations.

I've grouped the questions into 4 rough categories. Within each category, I've ranked the questions from most easy to ask to least easy to ask. I'd recommend either bookmarking this page (to find new questions as I continually update this list), or copying/pasting the list into your Notes app on your phone for easy reference.

Personal Preferences

1. What is your favorite feeling in the world?
2. What's the best compliment you could receive?
3. If you were able to live in one decade from the past in a specific place (100-110 in Rome, 1780s Philadelphia, 1860s Paris, 1920s New York, etc.) and then return to the present, which would it be, and why?
4. How would you like to be remembered?
5. In what ways and when have you been dishonest about your cultural tastes?

Personal History

1. Of all the factors leading to your success, which do you think is the most under-appreciated?
2. Which question can you ask to find out the most about a person?
3. What is your one piece of advice to everyone here?
4. If you had to pick two or three elements that explained your life, what would they be? Karl Ove Knausgard said there were only two for him: his abusive father and the fact that he never felt like he belonged anywhere.
5. What help could you most use that you haven’t asked for?

Personal Beliefs

1. What is the most significant thing you’ve changed your mind on in the last year? Why did you change your mind about it?
2. What conspiracy theories do you believe in?
3. What’s the closest thing to real magic?
4. What’s something you believe but can’t defend?
5. What is your most radical belief?

Personal Experiences

1. How has your life been different than what you’d imagined?
2. What’s your most important life lesson that you wish you learned ten years earlier?
3. Who was the last person you felt inspired by?
4. If you were to write a book, what might it be like, and what would it be about?
5. When was the last time you cried and why?

If you have any additional questions, shoot me a DM on Twitter and I'll update this page (with attribution, of course!)