The hardest part of a new friendship is often the first five minutes. “How are you?” invites “fine, you?”, and then silence. A good icebreaker is open, easy to answer and slightly personal, so it gives the other person something to talk about rather than something to defend.

Below are 30 questions, grouped by the kind of interest you might share. First, a few ways to use them well.

How to ask so the conversation keeps going

  • Answer first, briefly. Share your own answer, then ask. It makes the question feel like an invitation, not an interview.
  • Follow up on one detail. “Why that trail?” is far better than moving to the next question.
  • Use two or three, not all thirty. Treat the list as a menu. One good question that you actually follow is worth ten you rattle off.
  • Match the setting. Light questions work on a first coffee. Save the deeper ones for when you are already relaxed.

Questions about food and drink

  1. What is the best thing you have eaten this month?
  2. If you could only cook three dishes for the rest of your life, what would they be?
  3. What is your go-to order at a coffee shop, and has it changed?
  4. Is there a local place you recommend to everyone?
  5. What is a food you pretended to like and have given up on?
  6. What would you cook for someone you wanted to impress, and for someone you wanted to comfort?

Questions about the outdoors and fitness

  1. What is the best place you have ever been outside?
  2. Do you prefer a long planned trip or a spontaneous Saturday walk?
  3. What is something you tried once that you would happily do again?
  4. What is your favorite season to be outdoors, and why?
  5. What is the most unexpectedly beautiful spot you have found near where you live?
  6. What does your ideal weekend morning look like?

Questions about music, art and creativity

  1. What song never gets old for you?
  2. What was the last thing you made, wrote, drew or built?
  3. Is there a skill you would love to learn if time were no object?
  4. Which show, book or film do you recommend to everyone?
  5. Who introduced you to your favorite music?
  6. What is the best live show you have been to?

Questions about games, hobbies and downtime

  1. What is a hobby you could talk about for an hour?
  2. What is your all-time favorite game, board, video or otherwise?
  3. How do you like to spend a rainy day?
  4. What is something you are surprisingly competitive about?
  5. What is a small thing that always makes your day better?
  6. What are you currently trying to get better at?

Questions for when you want to go a little deeper

  1. What do you value most in a friend?
  2. When did you last feel really at home somewhere?
  3. What is something you changed your mind about in the last few years?
  4. What does a good week look like for you?
  5. Who is a friend you admire, and what do you admire about them?
  6. What is one thing you would like to do more of this year?

Let a shared interest do the work

The best icebreakers are the ones that come from something you really share. If you both enjoy hiking, “What is the best trail you have done?” beats any generic question, because you both have a real answer and probably a recommendation to swap. That is also the idea behind the challenges in KnownList, the friendship app we are building: short prompts drawn from the interests two people have in common, so there is always something real to talk about.

Once the conversation is flowing, do not let it fade. Suggest a specific plan within a week, as we describe in our guide to making friends as an adult. If it will be your first time meeting someone you met online, read the nine safety rules first.