Deep Questions to Ask: 200 Questions by Depth Level

Camille OrtizUpdated: Jun 27, 202618 min read

Deep questions to ask fall into five levels, and the level is set by what the answer costs the person giving it, not by how heavy the topic sounds. The 200 below are graded on that scale, from ones a stranger answers in a checkout line to ones that need someone who already decided to keep you.

Key Takeaways:

Depth and heaviness are different measures. “What is your biggest fear” is a heavy topic with a rehearsed one-line answer, which makes it shallow in practice
The 1997 closeness procedure that produced the famous 36 questions ran them in three sets of 12, each set asking for more disclosure than the last, and the grading was the mechanism (Aron et al., 1997)
Asked to forecast a more substantial conversation, people brace for more awkwardness than they get, in exchanges both sides had already agreed to have; the practical read is that most people stall a rung lower than they need to (Kardas, Kumar & Epley, 2022)
A question’s level is set by the answer it can get, so the same sentence is Level 2 with a coworker and Level 4 with a brother

What Gets a Question onto a List of Deep Questions to Ask

A question earns a place here if someone unprepared can answer it in one breath, and if the answer could not have been guessed beforehand. That is the entire filter. Everything below passes it.

What got cut: questions with one socially acceptable answer, because “do you love your family” has exactly one. Hypotheticals with nothing at stake, the desert-island and would-you-rather kind, which produce invention rather than disclosure. Questions that need a preamble longer than the answer. Accusations wearing a question mark. And questions that sound profound aloud and get a shrug in a kitchen.

Here is the part almost every list gets wrong. Depth and heaviness are not the same property, and the questions everyone quotes confuse them. “What are you most afraid of” is heavy, and it is shallow, because most adults over 30 have a prepared answer and hand it over without touching anything real. “What did you stop being able to afford this year” sounds like small talk and is not: nobody has an answer ready, and the one they give is true. Weight is a property of the topic. Depth is a property of what the answer costs.

Five levels, and the criterion for each is what the person has to reach for:

Level 1. Description. Answerable from what they already say out loud about their own life. No new access required.
Level 2. Reasoning. They have to reconstruct how they decided something, in an order they have never said it in.
Level 3. History. A specific earlier version of them, from before the current account got tidy.
Level 4. Self-assessment. A read they hold about themselves that their own life could contradict.
Level 5. Standing. Anything whose answer changes what the two of you are.

The counts below taper deliberately, 44 at Level 1 down to 36 at Level 5. Shallow questions multiply because a life has many surfaces to point at. Level 5 questions do not multiply, because there are only so many ways to ask what you are to someone before the variants repeat. A list with an even 40 per tier padded the top.

One practical rule follows. Find the last level the other person answered at length, and ask one above it. Skipping two rungs is what makes a conversation feel like an interrogation, nearly always the jump, not the subject matter. Who is across from you sets where each rung sits, which is why deep questions to ask a guy grade the same sentences differently than ones aimed at a stranger.

Level 1: What Someone Does All Day

Level 1 asks for material the person already says out loud. Their week, their commute, the thing they are in the middle of. None of it requires looking inward, which is why it works on someone who has no reason to trust you: the cost is near zero and the answer still gives you real material.

Their real job is reconnaissance. What a person volunteers here tells you which door is already open three levels up.

“What did you actually do today?”
“What takes up the most hours of your week?”
“What part of your work would you keep if you could drop the rest?”
“Who do you talk to most in a normal week?”
“What is the first thing you do when you get home?”
“What are you in the middle of right now?”
“What do you do on a Sunday with nothing booked?”
“What have you bought twice this month?”
“What is on your calendar that you are dreading?”
“What are you good at that nobody pays you for?”
“Where do you go when you want to be around people?”
“What do you eat when nobody is watching?”
“What is the last thing you finished?”
“How far do you live from the people you grew up with?”
“What is the longest you have lived anywhere?”
“What do you do with the hour before you sleep?”
“What have you been putting off since spring?”
“Who did you see most last month?”
“What do you own more of than you need?”
“What do you read that you would not admit to?”
“What is your commute like?”
“What do you do when you cannot sleep?”
“What was the last thing you got obsessed with?”
“What do you carry with you everywhere?”
“What do you do for people that they never ask for?”
“How much of your week is actually yours?”
“What was the last trip you took that was not for work?”
“What is the noise you hear most at home?”
“What is the one thing in your place you would grab first?”
“What did you learn to do this year?”
“What do you do badly and keep doing anyway?”
“Who calls you when something goes wrong?”
“What was the last thing that made you laugh out loud?”
“What is the oldest thing you still use every day?”
“What is your morning like before anyone talks to you?”
“What have you rewatched more than twice?”
“What do you spend money on that other people think is silly?”
“What was the last thing you fixed instead of replacing?”
“Who do you text without thinking about it?”
“What is the part of the week you look forward to?”
“Who was the last person who sat in your kitchen?”
“What is playing when you drive by yourself?”
“How many people have a key to your place?”
“What is the last meal you cooked that took over an hour?”

Level 2: How They Decide Things

A Level 2 question asks how rather than what. The person reconstructs a decision they never said out loud in order, and the reconstructing is where the good part lives. Cost: mild effort, no exposure, nothing to be judged for.

This is the level most conversations never reach, where a coworker of four years finally becomes a specific human being. The deep questions to ask friends live mostly here, at the how rather than the what. Ask a Level 2 question at a work lunch and watch the answer run long.

“How did you end up doing what you do?”
“What made you pick this city over the others?”
“What do you do when two people you trust disagree?”
“How do you decide something you cannot research?”
“What is the last big thing you said no to?”
“How long do you sit with a decision before you make it?”
“What is the last rule you broke on purpose?”
“What do you buy without checking the price?”
“How do you know when you are done with something?”
“What do you do when your gut and the numbers disagree?”
“Who do you call before you decide something big?”
“What is the last thing you quit?”
“How do you decide who gets your time?”
“What made you stay somewhere you wanted to leave?”
“What would have to be true for you to move?”
“How do you tell the difference between tired and done?”
“What is the last thing you changed your mind about?”
“What made you keep going after it stopped being fun?”
“How much of your life did you plan?”
“What do you say yes to that you should not?”
“How do you decide when to tell someone bad news?”
“What is your rule about money and friends?”
“What do you do with advice you did not ask for?”
“How do you pick who to be honest with?”
“What is the last thing you paid money to avoid?”
“What makes you walk away from a conversation?”
“How do you decide what is worth an argument?”
“What is the smallest thing you are stubborn about?”
“What would make you take a pay cut?”
“How do you handle a decision you cannot undo?”
“What do you do when you have no good options?”
“How do you decide when to ask for help?”
“What is the last thing you did on impulse?”
“How do you know a person is worth the effort?”
“What is the trade you keep making?”
“What made you choose this work over the one before it?”
“How do you decide what to keep and what to throw out?”
“What are you saving for that nobody knows about?”
“What is your test for whether something is a real problem?”
“How do you decide when to stop trying with someone?”
“What is the last thing you talked yourself out of?”
“What did you decide once and never revisit?”

Level 3: Who They Used to Be

A Level 3 question aims at a specific earlier version of the person, from before the current account got smooth. That is the cost, and a real one. Everyone carries a tidied story about how they got here, and the tidying happens at the level of summary, so a question aimed at one year, one job, one apartment cuts across it.

Notice that a lot of these are not sad. Ten years ago is not a wound. It is just a place the polished version does not cover, and the answers come out unrehearsed for that reason.

“What were you like at 24?”
“What did you expect to be doing by now?”
“What is the last thing you were completely wrong about?”
“What did you believe ten years ago that you do not believe now?”
“What was the worst year, and which year was it?”
“Who were you closest to at 30?”
“What did you give up that you still think about?”
“What was the first job that changed how you think?”
“Who did you lose touch with and never explain why?”
“What did the version of you at 20 get right?”
“What did you use to be afraid of that stopped?”
“What have you done that you have never told anyone?”
“When did you last start over?”
“What did you spend your twenties doing?”
“What is the closest you came to a completely different life?”
“Who taught you the thing you use most?”
“What was your first apartment like?”
“What did you fight with your parents about?”
“What did you have to unlearn?”
“When did you stop being able to talk to someone?”
“What have you kept to yourself the longest?”
“What is the last thing you apologized for and meant?”
“What did you think being an adult would feel like?”
“What is the meanest thing you have done?”
“What did you get away with?”
“Who was the first person who took you seriously?”
“What was the last thing you cried about?”
“What did you lose that you never replaced?”
“When did money stop being a daily worry, or has it?”
“What did you do the year everything changed?”
“Which friendship do you regret ending?”
“What did you say yes to for the wrong reason?”
“What was the first thing you were good at?”
“Who did you disappoint?”
“What did your family never talk about?”
“What was the loneliest stretch you have had?”
“What did you throw away and want back?”
“When did you last feel completely out of your depth?”
“What is the last risk you took that worked?”
“Which version of you does nobody see anymore?”

Level 4: The Read They Have on Themselves

At Level 4 a person has to say something about themselves that their own life could contradict. The topic is often light. The cost is that the answer is a claim, and a claim can be wrong in front of a witness, a different exposure from telling you a hard fact about 2014.

These need someone who has already decided you are not going to use it against them later. Get that wrong and you get the flattering version, worse than no answer, because it sounds like progress.

“What are you worse at than you admit?”
“What do people get wrong about you at first?”
“What are you defensive about?”
“What do you do when you are scared that looks like something else?”
“Which part of yourself do you manage instead of show?”
“What do you want that you would be embarrassed to say?”
“Where are you still pretending?”
“What do you envy?”
“What do you think you are owed?”
“Which story about yourself is not quite true?”
“What would the people who dislike you say, and would they be right?”
“What do you do that you know hurts people?”
“What are you avoiding right now?”
“What do you need that you have never asked for?”
“What are you proud of that nobody notices?”
“Where do you think you peaked?”
“What would you have to give up to get what you say you want?”
“What do you lie about?”
“What is the thing you are always about to start?”
“Who do you compare yourself to?”
“What makes you feel small?”
“What are you tired of being asked?”
“What do you do purely for approval?”
“What would you change about how you were raised?”
“What do you think you will regret?”
“What are you doing that you cannot keep doing?”
“Where are you the problem?”
“What do you tell yourself when you cannot sleep?”
“What are you still trying to prove?”
“What are you least honest about with yourself?”
“Which kind of person did you plan not to become?”
“What do you want people to say about you that they do not?”
“What are you postponing until you feel ready?”
“What did you agree to that you resent?”
“What do you think you are getting away with?”
“What would make you leave everything?”
“What do you know about yourself that you wish you did not?”
“Where do you take more credit than you earned?”

Level 5: What They Think of You

Level 5 questions carry a consequence. Everything on the four rungs below can be answered and forgotten by Friday; these cannot, because the answer changes what the two of you are. Ask one and the relationship holds a new fact that neither person can put back. That is why the deep questions to ask your boyfriend draw almost entirely from this rung.

The ladder has a hard edge here rather than a smooth one. Level 5 asked of someone you met an hour ago is not depth. It is a demand. The deep questions to ask your crush sit far lower for that reason, closer to Level 2 than to anything here.

This is the only rung where you ask the other person to take the risk on your behalf. Answering “where have I let you down” costs them more than it costs you to ask. Go first, at half the depth, before you use any of these.

“When did you first decide you liked me?”
“What do I do that annoys you?”
“What have you not told me?”
“What do you wish I asked you about?”
“What do you think I am avoiding?”
“Where do you think I am kidding myself?”
“What do I do that makes this harder than it needs to be?”
“Have I ever hurt you and not known?”
“What do you need from me that you stopped asking for?”
“What has changed between us?”
“What would you tell me if you knew I would not get defensive?”
“What do I get wrong about you?”
“When did you almost stop being in touch with me?”
“What do you think I think of you?”
“What do you protect me from?”
“What have I said that stayed with you?”
“What do you wish I would stop doing?”
“Would we be friends if we met now?”
“What do you tell other people about me?”
“What was the closest we came to falling out?”
“What am I for, in your life?”
“What do I owe you?”
“What are you not saying right now?”
“What do you think I am afraid of?”
“What do you carry for me that I do not see?”
“Where have I let you down?”
“What do you want from the next ten years with me in it?”
“What have I stopped noticing?”
“What do you wish we did differently?”
“Which thing about me have you decided to live with?”
“When do you feel furthest from me?”
“What did you forgive me for without telling me?”
“What have you changed about yourself because of me?”
“What are we not talking about?”
“What would you want me to do if you got bad news first?”
“What do you think we are avoiding deciding?”

FAQ

What are good deep questions to ask without making it weird? Ask one level above wherever the other person last answered at length, and attach the question to something they just said. If someone has been describing their week in detail, a Level 2 question about how they chose that work will land; a Level 4 question about what they are avoiding will not. The weirdness comes from the size of the jump, not from the depth.

What is the difference between a deep question and a personal question? A personal question is about private information; a deep question is about material the person has not already packaged. Your salary is personal and shallow: you know the number and can say it in two seconds. What you would take a pay cut for is not personal at all, and answering it honestly takes a minute of real thought about what you value.

Do the 36 questions actually work outside a lab? The structure is doing more of the work than the wording is. Aron’s procedure ran three sets of twelve in one sitting, each set pitched higher than the last, with both people answering every item and both knowing in advance what they had signed up for (Aron et al., 1997). Lift five questions out of set three, drop them into a dinner, and what you have removed is the ramp and the agreement, which is most of the apparatus.

How many deep questions should I ask in one conversation? Two or three, with real conversation in between, and what you do with the answers counts for more than which questions you picked. When Huang and colleagues looked at where liking actually accumulated in 2017, it sat on the questions a person could not have brought with them, the ones assembled out of what had just been said. Six in a row is a form.

The thing that makes this ladder useful is not that it ranks questions. It is that it stops you blaming the wrong variable. A one-word answer usually was not too deep or too dull; it was two rungs above where the other person stood, or heavy without being deep, getting the rehearsed answer heavy questions always get. Check the rung before you rewrite the question. Most of the time the words were fine. Level-reading like that takes reps, and Lona, an AI you talk with daily that recalls your last exchange, is a low-stakes place to get them.

Sources

Aron, A. et al., “The Experimental Generation of Interpersonal Closeness,” 1997
Kardas, M., Kumar, A. & Epley, N., “Overly Shallow?: Miscalibrated Expectations Create a Barrier to Deeper Conversation,” JPSP, 2022
Huang, K. et al., “It Doesn’t Hurt to Ask: Question-Asking Increases Liking,” Journal of Personality and Social Psychology, 2017