Questions to ask your best friend: the deep, the funny, the never asked

The best questions to ask your best friend are the ones you've never asked. You know how they take their eggs, the name of their first car and the haircut they'd rather forget. You can still go a decade without asking the questions that would surprise you both. The lists below are for a friend you've known a long time, in four short groups: questions you never asked, questions about the friendship itself, funny ones and deep ones.

An example: Callum and Arjun met at 23, when they shared a drafty two-bedroom apartment with a broken oven. They're 44 now. Every October they walk the same ridge trail and eat their sandwiches on the same flat rock. This year, between bites, Callum asked something he'd never asked in twenty years: "Why did you say yes the first time I asked you to hang out?" Arjun laughed until he had to set his sandwich down on the rock. Then he told a story Callum had never heard, about a lonely first month in a new city and a roommate who knocked on his door with two spare tickets to a basketball game.

Why an old friend still has answers you haven't heard

Long friendships run on shared stories. You tell the same ones, laugh in the same places and finish each other's sentences. That's part of the comfort, but it also means you can talk about the same few things for years.

People keep changing, though. Your friend at 44 isn't your friend at 23, and some of the stories that shaped them happened on days you weren't there. A new question is an easy way to get to know the person your friend is now.

Questions you never got around to asking

Some of these look simple. Many get a story you haven't heard.

1. Back at the start of our friendship, where did you guess I'd end up?
2. Why did you say yes the first time I asked you to hang out?
3. The year we got close, what were you dealing with that I never knew?
4. Who were you trying to be in your twenties?
5. Which of your skills have I somehow never seen in action?
6. Which of your parents do you sound like when you're tired?
7. Which big choice did you make without running it past me first?
8. What was your plan for life before this one took over?
9. What have you wanted to try for years without telling a soul?
10. What's a question you've always hoped I would ask you?

Questions about the two of you

These turn the talk to the friendship itself. They work best when you're both relaxed and nobody is in a hurry.

1. Which year of our friendship was the best one, in your view?
2. Which of our traditions would you fight to keep?
3. What's a fight we had that you're glad we had?
4. What do you think we'd be like if we'd met ten years later?
5. What's one thing about our friendship other people don't get?
6. Which of our shared stories do you tell other people most often?
7. Which of my sayings has slipped into the way you talk?
8. What should we stop doing because we've outgrown it?
9. Where do you picture the two of us in twenty years?

Funny questions for the friend who knows all your stories

Old friends make the best audience for silly questions, because every answer comes with years of evidence.

1. If we were a comedy duo, what would our act be called?
2. If we were stranded somewhere with no map, which of us would get us home?
3. What's the dumbest thing the two of us have ever argued about?
4. Which of my outfits from the old days should never come back?
5. If you had to describe me with one kitchen object, which one would it be?
6. Which ridiculous plan of ours came closest to actually happening?
7. Which one of us is the worse driver, honestly?
8. What's the weirdest thing you've seen me eat?
9. Which of my phrases do you do an impression of when I'm not around?
10. If you spent tomorrow living my day, which part would puzzle you most?

Deep questions for a long walk or a quiet evening

Save these for a day with nowhere else to be. A walk works, and so does a long car ride or a slow evening at home.

1. What's something you're still figuring out about yourself?
2. What about getting older do you actually like so far?
3. If someone asked me who you really are, what would you want me to say?
4. Has what you want from me as a friend changed since our twenties?
5. Outside the two of us, who has changed you the most?
6. If you could talk to your younger self for an hour, which year would you pick?
7. Where do you feel you belong right now?
8. What would you go after if you knew I'd back you no matter what?
9. Which part of your life these days do you think I see wrong?
10. What worries you a little about the coming decade?

When an answer surprises you

After twenty years, it can sting a little to learn something new. Maybe your friend names a best year you barely remember, or a big choice they made without you. Try not to argue with the answer. Ask one more question instead, like "What made that year so good?" or "What was going on for you then?"

Answer the questions yourself, too. A best friend who gets asked ten questions in a row starts to feel like a guest on a talk show. Take turns, and let one good answer fill the whole evening if it wants to.

Why best friends are often so different

Some long friendships pair two people who don't look alike at all on paper. Often one of you plans and the other improvises, or one talks in feelings and the other in facts. That difference shows in how each of you answers the questions above.

Typeza describes 16 personality types, and one of the relationship types between them, Duality, often fits a best friend. Two duals take in the world through different kinds of information, so each easily offers what the other finds hard to come by. Here are three dual pairs among the 16 types:

• Ideator answers the funny questions with five wild ideas at once. Harmonizer answers with a memory of one perfect evening, down to the food and the light in the room. Between them, they cover fun and rest.
• Mentor turns a deep question into a long story full of feeling. Inspector answers the same question in two careful sentences and means every word. The Mentor brings warmth, and the Inspector brings a steady order.
• Diplomat answers "Where do you picture us in twenty years?" with a plan for next Saturday. Strategist has already thought about the next ten years and isn't sure where to start. One keeps the friendship lively now, and the other keeps an eye on where it's going.

All of this describes typical patterns in type theory. It isn't a rule about you and your friend, and it isn't advice. Friends of any two types can stay close for life. What makes a best friend looks at Duality and other close bonds in more detail.

Other lists for an evening with friends

For lighter fun with any friend, try these random questions to ask your friends. To hear how your friends honestly see you, pick a few questions to ask your friends about yourself. And to turn it into a game of who knows whom best, use these how well do you know me questions.

Find out how you and your best friend fit together

Typeza shows the two of you something a list of questions can't: the relationship type between your personalities, which parts of your friendship tend to feel easy and where you might see things differently. Start by taking the free friendship compatibility test yourself. Then hand the link to your best friend and read your two results together.

Questions people ask

What are good questions to ask your best friend?

Questions you've never asked work best with an old friend, like why they said yes to hanging out the first time or which year of your friendship was the best. Mix in a few funny ones so it feels like a talk and not a quiz.

What are deep questions to ask your best friend?

Try "What are you still figuring out about yourself?", "Who has changed you the most?" or "Where do you feel you belong right now?" Ask them on a walk or a quiet evening, and answer them yourself too.

What are funny questions to ask your best friend?

Ask what your comedy act would be called, which of you is the worse driver or which of your old outfits should never come back. Questions with years of shared history behind them get the biggest laughs.

How many questions should you ask in one go?

Three or four good ones are plenty for one evening. A single question can fill a whole walk if the answer turns into a story.

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