Deep questions to ask friends: 50 that go beyond small talk

Every September the same thing happens: the group gets back together after summer, everyone shares where they went on holiday, and then the conversation stalls on work and the weather. Yet these evenings are exactly when you could find out how your friends are really doing. Deep questions to ask friends are the simplest tool for that: one question, one honest answer, and the round moves on.

We put together 50 questions across five levels. The first ones are easy warm ups, the last ones are deep enough to surprise even a ten year friendship. You do not have to go in order, just pick whatever suits the mood.

How to play: turning questions into a game

The rule is simple: go around the circle, and each person asks a question to the friend on their left. Whoever answers then asks the next one. Unlike Truth or Dare, there is no dare to escape into, so you need one exception: everyone gets a single pass per evening, no explanation needed.

If nobody wants to come up with questions, read them out from a phone. The one thing that matters is that the person asking also answers when the question comes back to them. The game works because everyone gives the same amount of themselves.

Warm up questions to ask friends

The first round needs light questions that everyone has a quick, funny answer to. They are not personal yet, but they already say more than the usual catch up.

1. What was the best moment of your summer that you have not told anyone about?
2. What everyday thing would you happily overpay for?
3. What is the strangest thing you learned recently?
4. Which show would you rewatch as if it were the first time?
5. What food did you hate as a kid and love now?
6. If you had a different job starting tomorrow, what would it be?
7. Which app would make your life easier if it disappeared?
8. What is the most useless thing you have ever bought?
9. Which song do you know start to finish, even if you are embarrassed about it?
10. What was the last thing you laughed out loud at on your own?

Deep conversation questions

Once the circle is warmed up, move on to questions that cannot be answered in one word. Slow down here and let a single answer turn into a conversation.

1. What opinion have you completely changed in the last few years?
2. What are you most proud of that you rarely talk about?
3. What would you do differently if nobody would ever find out it was you?
4. What advice did you get that only made sense years later?
5. What scares you more: failing, or never trying?
6. Which decision turned out best for you even though it felt wrong at the time?
7. What do you feel everyone else has figured out except you?
8. Who do you owe the most to, and do they know it?
9. What would a perfect ordinary Tuesday look like for you?
10. Which habit would you love to drop but cannot?
11. When was the moment you first felt like an adult?
12. If you did not have to work for money for a year, how would you spend it?

Deep questions to ask friends you have known forever

The strange thing about old friends is that we assume we know everything about them. These deep questions to ask your friends show how much has changed since you last really talked.

1. What do you think everyone gets wrong about you?
2. When did you last feel that this friendship really matters to you?
3. What have you learned from me, maybe without me noticing?
4. Which decision we made together do you regret, and which one are you proud of?
5. What did you think of me when we first met?
6. How have you changed the most in the last five years?
7. What would you like help with but have not dared to ask?
8. What is the one thing you still want to do with all of us?
9. What is hard right now but does not show from the outside?
10. Where do you see yourself in ten years, and are we still in the picture?

Late night questions: love and relationships

After midnight, when only the inner circle is left, these questions come up on their own. They are personal but not awkward, and everyone decides how much they share.

1. What was your biggest mistake in love?
2. Which trait could you never live with in a partner?
3. What did you learn from your last breakup?
4. Do you believe a person has one great love?
5. What romantic gesture do you find cheesy but would secretly enjoy?
6. When did you realise someone meant more to you than you thought?
7. What do you think is the biggest mistake most couples make?
8. What would you never give up for anyone in a relationship?

Questions about your shared history

To close the evening, nothing beats questions that everyone remembers differently. A story is guaranteed to come up that someone has been telling wrong for years.

1. Which party together do you think back to the most?
2. What is the dumbest thing we ever did together?
3. When did we laugh the hardest?
4. When were you angriest with us but never said it?
5. Which trip together would you repeat tomorrow?
6. What story about us would you never tell your parents?
7. Who has changed the most since we all met?
8. Which tradition of ours do you want to keep even if we all move far away?
9. What is your first memory of me?
10. If we could relive one evening together, which one would it be?

Ground rules so nobody feels cornered

• Everyone gets a pass, and a pass gets no follow up or comment.
• What is said at the table stays at the table. No screenshots, no retelling.
• Whoever asks also answers if the question is turned back on them.
• Do not ask anything you would not want to answer yourself.
• If someone gets emotional, the round stops. The game can wait, the friend cannot.

If you would rather not invent the questions

Party Games by Guessy has categories made for exactly these evenings: Deep & Personal in Truth or Dare, Deep in Would You Rather, and Emotionally Deep in This or That. The deep categories are part of premium, the basic questions are free, and the app never repeats a question, so you are not asking the same thing ten rounds later.

The takeaway

A good evening of deep conversation questions is not made by the questions, it is made by everyone actually listening to the answers. Pick five deep questions to ask friends from this list for your next get together, and notice how much longer the conversation lasts than when you just ask what is new.

For more, Cards by Guessy has a full list of deep questions in eight themes, plus questions to get to know someone.