Deep questions to ask friends, and what they show about your friendship

Deep questions to ask friends are open questions about your friend's life, hopes and worries, and about the friendship itself. They are about the friend. If you want to hear what friends think of you, questions to ask your friends about yourself covers that. For couples, see deep questions to ask your partner.

An example: Lena and Jo have been friends since they were 19. Now 34, they meet once a month for dinner and talk about work, partners and the next holiday. One night Lena asked, "What do you think you'd be doing if you hadn't moved here?" Jo put down her fork. "Honestly? Running my grandmother's bakery. I think about it every week." In fifteen years, Lena had never heard a word about it.

Why ask a friend deep questions?

Long friendships run on habit. You know your friend's coffee order, their partner's name and where they go on holiday. You may not know what they are afraid of now, or what they would change about their life if they could.

People keep changing through adult life, often more than their friends notice. A friend you have known for twenty years can be a stranger in a few areas. A deep question now and then keeps the friendship up to date. It also shows that you are still curious about them.

Good questions to ask your friends to start

These are light but real, good for warming up or for a friend you are still getting to know. For someone you have only just met, how to get to know someone has easier first questions.

1. What has been the best part of your week, and why?
2. What are you into right now that I don't know about?
3. What is a small thing that always cheers you up?
4. Which place would you go back to tomorrow if you could?
5. What is something you changed your mind about this year?
6. Who do you text first when something good happens?

Questions about their life and what shaped them

1. What were you like at sixteen, and what would you tell that person now?
2. Which family member are you most like?
3. What is a hard time you got through that I don't know much about?
4. What did your parents get right, and what would you do differently?
5. What is a lesson you learned the hard way?
6. What is a memory you go back to when you need to feel good?

Questions about what they want and worry about now

1. What would make this year a good one for you?
2. What keeps you up at night lately?
3. If you could change one thing about your life tomorrow, what would it be?
4. What are you proud of that you never talk about?
5. What do you wish you had more time for?
6. What would you do if you knew nobody would judge you?

Questions about your friendship

These are about the two of you. They can feel strange to ask, especially between friends who never talk about the friendship itself. Ask them one to one.

1. What is your favorite memory of us?
2. What do you think keeps our friendship going?
3. Is there a time I let you down that we never talked about?
4. How do you like to be supported when things go wrong?
5. What should we do together that we have never done?
6. Do you feel we see each other enough?

With a friend of many years, questions to ask your best friend has more of these, plus a few funny ones.

Questions for a friend going through a hard time

When a friend is struggling, a deep question can feel like pressure. Keep these gentle, and let them say no.

• What would help most right now, even something small?
• When you tell me a problem, should I help solve it or just hear you out?
• What has been the hardest part?
• What is one thing that went okay this week?
• Is there something you have been carrying alone?

The second question saves a lot of trouble. Many friends want to be heard first and helped later, and some want it the other way round. Our guide on how to cheer someone up has more ideas for a friend's bad week.

Good questions to ask a group of friends

Group questions are lighter, because few people want to share their deepest worries in front of six others. These still go well past small talk.

• What is something your family did that you thought was normal until you left home?
• What is a risk you took that paid off?
• Which year of your life would you live again?
• What is the best advice anyone has ever given you?
• What did you believe as a kid that turned out to be wrong?
• What is a skill you wish you had learned earlier?

Go around the table so everyone answers, and let anyone pass. On a sillier night, random questions to ask your friends keep things light, and a table that loves to argue can try philosophy questions.

What their answers tell you

• Where they are in life now. An answer about worry or hope shows you what fills their head this year, which can be very different from five years ago.
• What they need from you. A friend who talks about being tired may need practical help more than a night out.
• What they keep for later. A joke or a quick change of subject often means "not yet". Ask again some other time, in private.
• How they think. Some friends answer with a story, some with a list and some with a question back. That says a lot about who they are.

Why some friends answer deep questions easily and others don't

You ask two friends the same question. One talks for an hour, and the other says "No idea" and orders another drink. Neither is a worse friend. Personality is part of why some questions feel natural to answer.

Six of the 16 types in Typeza show the difference well:

• Harmonizer: warm and easy company, happy to talk about comfort, food and the people they love. Big questions about the meaning of life can bore them, so ask about real moments.
• Commander: direct and practical. A question about feelings may get a short answer, but ask what they are working toward and they will talk.
• Strategist: quiet, and thinks in long time spans. Ask where they see things going in ten years and they will surprise you. Put on the spot in a group, they may say nothing at all.
• Guardian: loyal and warm with people they trust, and closed with everyone else. They answer deep questions one to one, after years, not at the second meeting.
• Counselor: gentle and good at reading people, and often the one who asks the deep questions. They can find it harder to answer them about themselves.
• Encourager: curious about everything and full of ideas. A "what if" question gets a flood of answers, and a question about routine or money gets a shrug.

Read these as tendencies. The relationship type between two friends matters too. In some pairs, like Duality, the fit shows once you are close, and then deep talk comes easily. In others, you need more time to find the questions that work for both of you.

Tips for a deep talk with a friend

• Choose one to one. Many people open up more without an audience. A long call works too, if you live far apart.
• Do something together. A long walk, a drive or cooking side by side takes the pressure off.
• Go first. Answer your own question, so it doesn't feel like an interview.
• Follow up before moving on. "What happened then?" goes further than the next question on your list.
• Keep what they tell you private. One leaked secret can undo years of trust.
• Don't force it. If a friend changes the subject, let them. You can ask another day.

See what kind of friends you are

Deep questions show you a friend's story. A personality test shows how each of you tends to think, and how the two of you fit. The free test lives on the friendship compatibility test page, and it asks you to choose the more fitting of two statements, again and again. Your type appears as soon as you finish, with no account needed. Your result carries an invite link, so pass it to the friend you most want to understand. When your friend has finished too, your shared relationship type appears, and it may explain why one question opens them up while another gets a shrug.

Questions people ask

What are deep questions to ask friends?

Three to start with: "What keeps you up at night lately?", "What is your favorite memory of us?" and "What would you do if you knew nobody would judge you?"

What are good questions to ask a friend?

Good ones are open and a little personal, like "What are you into right now that I don't know about?" or "Who do you text first when something good happens?" They start a story instead of a one word answer.

What are 20 questions to ask a friend?

Take three or four from each group in this article, starting light and ending with a question about your friendship. Twenty in one night is a lot, so spread them over a few meetings.

How do you have a deep conversation with a friend?

Pick a quiet one to one moment, ask one open question and follow up on the answer. If you'd rather start from a topic than a question, deep conversation topics has lines to open with.

What if my friend doesn't want to answer?

Let it go without a fuss. Some people need years of trust, or a different setting, before they open up.

Written by Virko Kask, founder of Typeza
Written with the help of AI tools.