Here are some questions I’ve found fun to ask people I’ve just met to get to know them. I’ve found that good conversations start from questions that get your (future) friend to:

  1. recall an emotionally charged memory (positive or negative)
  2. recall a rarely accessed memory (nostalgia)
  3. generate a novel response (think about something they hadn’t thought about before).

Bad conversations occur when the person you’re talking to is:

  1. providing canned responses to questions, having a conversation with you that they have had with someone else a moment ago
  2. not learning anything about themselves
  3. not feeling understood by you

Soft ball

  • How did your parents meet?

I generally start with this one because you never really know a person unless you know their pre-history.

  • What was your favorite thing to do at recess in 3rd grade?

Usually conjures up a warm memory.

  • What’s a decision you’re trying to make right now? Do you want to walk me through your thinking?

Switches the conversation in a direction where you can be helpful to them.

  • What thing did you buy for under $50 that brought you the most joy/convenience/utility?

Helps you learn what the best customer experience is, and what kind of solution this person in particular values (something that saves them time (random developer tool), something that saves them in a pinch (portable battery charger), something that helped them get excited about a new hobby (new running shoes)…etc.

  • What do you believe most strongly that you can’t prove?

Very variable responses, generally gets them to distill their emotional state into a heuristic/philosophy they use in life, “people generally do the right thing”, “people are generally selfish”, “i’m meant to do great things”, etc.

  • What do people misunderstand about you when they first meet you? What do your best friends know about you that your acquaintances don’t?

Gives them a chance to share who they really are with you vs. how they may come across at first meeting.

Hard ball

  • What is the best gift you’ve been given?

This gives you a sense for what they value most. Some people say specific material things like “a car”, some people say an experience “a vacation to Tokyo” or “my college education”, others say personality traits like “my parents taught me to be hardworking”. There’s usually another story around how they got their gift, and if you end up liking them and wanting to treat them in the future here’s a hint for how to get them something they really want.

  • What is the best gift you’ve ever given someone else?

One of the ways to think about what kind of company to start or what kind of work to do is to think about what the best gift you could give to someone (or to the world). This is a proxy for how aligned their life is in terms of what they think is most valuable to give to others and what they actually spend their time giving to others.

  • What is the most significant thing you’ve changed your mind on in the last year?

Litmus test for if they are growing/changing or are in a static/settled place.

  • What negative emotion do you feel most often?

Gives you a chance to be vulnerable/authentic with each other about the less rosy parts of life.

  • What are you most worried about right now?

Another chance to be genuine about what is on your mind and to be there for each other.

Most people squirm/try and get out of answering these

  • What is your most radical belief?

Gives you a sense for if they think independently. Call them out if what they say is something you’ve heard before or 30%+ of the people in the room would agree with what they say is their most “radical” belief.

  • What misconception is most common among your friends/coworkers/family?

Gives you a sense for if they think independently (do they see anything differently than the people they spend the most time with)?

  • What’s something nobody will tell me, that I should know? What is something you discovered in your life that society/employers/friends conceal that is important to know?

Gold! Don’t let them get away with a platitude or with something that isn’t actually concealed.

  • Do you think it’s more important to know the “written” rules or the “unwritten” rules? What is an unwritten rule you discovered?

Gold! Don’t let them get away with a rule you’ve read or heard somewhere else.

When meeting a couple…

  • What is your love story? Who did the wooing?

This is a better variant of “how did you meet” because you get to hear the tale of how they won each other’s hearts.

  • When did you know you loved him/her?

Make sure to prod for a specific moment/event.

  • What do you love most about him/her?

Gives them both a chance to rave about each other.

  • What was the most romantic thing he/she did for you?

There’s a gushy story here.

Closing Thoughts

In general, I think what makes getting to know new people fun for me is finding out what the other person knows a lot about, whether it’s a scientific topic, a city I haven’t been to, or a hidden trail to hike.