Most lists like this are 30 restatements of the same question. This one is not, because I use these, and a question that does not produce something new is dead weight I would have stopped asking years ago. They are grouped into 6 sets of 5 so you can take one set on one evening rather than trying to do all 30 and giving up somewhere around number 9.
A warning before you start. These are good questions, which is exactly what makes them dangerous. A good question opens a door and then you are both standing in a room you did not plan to be in on a Tuesday. So read the ground rules first. People who skip the rules and go straight to question 23 tend to email me afterward.
How to run these without starting a fight
The failure mode is predictable. One of you brings the list with an agenda, asks the question you actually wanted to ask, and the other one correctly identifies that this was an ambush wearing a worksheet. Then you have a fight about the list.
The ground rules
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One set per sitting. Five questions, then stop, even if it is going well. Especially if it is going well. Nobody has ever regretted ending a good conversation early.
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Both of you answer every question. If only one person is being examined, this is an interrogation and it will be treated as one, correctly.
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No rebuttals for 24 hours. You are allowed to ask a clarifying question. You are not allowed to correct their answer, because their answer is not a claim about reality, it is a report on their experience.
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Skip anything that is currently on fire. If you had a fight about money on Sunday, do not open with the money set. Pick a set that is not the live wound and build some credit first.
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Write down the one thing you want to come back to. Not the whole conversation. One line each. Most of the value in these shows up 3 days later, not in the moment.
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Nobody gets to use an answer as evidence later. Ever. Break that rule once and you will never get an honest answer from this person again, and you will have taught them something expensive.
If your last several attempts at a real conversation have gone sideways regardless of the topic, the problem is upstream of any question list and I would start with how to improve communication in marriage before you try this.
Set one: where we actually are
Start here even if it feels basic. Most couples discover in this set that they have been describing entirely different marriages to their friends.
1. What is the one word you would use for how our marriage has felt in the last 6 months. Not the last week, the last 6 months. One word forces past the diplomatic answer, and the word people choose is almost never the word their partner expected.
2. When did you last feel genuinely close to me, and what was happening. The date matters less than the answer to what was happening. That is the recipe, and most couples have not looked at it in years.
3. What do you think I would say is the hardest thing about being married to me. Answering for yourself is easy. Answering as your partner is where the actual self awareness lives, and it is a fair way to check whether you have been paying attention.
4. What is something you have stopped mentioning because it never goes anywhere. This is the drawer question. Every marriage has a drawer, and everything in it is still fully charged.
5. On a normal Wednesday, do you feel like my partner or my colleague. The colleague answer is not a crisis. It is the most common condition I treat, and it has a name and a shape, which I lay out in what a parent marriage is.
Set two: how we talk and how we fight
Everybody thinks their communication is the problem. Usually the problem is narrower than that and it lives in what happens after the disagreement rather than during it.
6. What do I do in an argument that makes you stop being honest with me. Not what upsets you. What makes you go quiet or start managing me. Those are different and only one of them ends conversations.
7. How do you know when a fight between us is actually over. A large share of couples discover here that one of them thinks the fights end and the other thinks they get filed.
8. What is a thing I say that lands much harder than I think it does. Everyone has one. It is usually 4 words long and has been in service for a decade.
9. When you have something difficult to tell me, what do you do in the hour beforehand. The rehearsal is where the honesty gets lost. If your partner drafts and edits before they speak to you, that is information about the room, not about them.
10. What would have to be true for you to say the difficult thing immediately instead of a week later. Ask this one and then genuinely be quiet.
Watch for the pause
The most useful moment in this whole list is not an answer. It is the pause before one. When your partner stops for 4 seconds and then gives you a slightly smaller version of what they were about to say, that is the actual material. Do not chase it in the moment. Note it and come back to it on a calmer day.
Set three: money, work and the load
This is the set people skip, and it is the set that quietly determines the temperature of most houses I sit in.
11. What does money mean to you, before we talk about numbers. Safety, freedom, status, proof you are not your father. Two people arguing about a purchase are almost never arguing about a purchase.
12. Which invisible jobs in this house do you think I do not see. Not the visible tasks. The remembering, the scheduling, the noticing that the shoes no longer fit.
13. If we split everything the way it is actually split today, would you call it fair. Not equal. Fair. And notice that the honest answer here changes about 3 times a year in a house with young children.
14. What part of your work do I not understand. Plenty of resentment in a marriage is one person believing the other's day is easier than it is, purely because they have never had it described properly.
15. What is one thing you have given up since we had children that you have never said out loud. Ask gently. The answer is often a version of the person they used to be, and it takes a minute to reach.
Set four: affection, desire and the bedroom
Do not do this set first and do not do it after a bad day. And do not do it in bed, which is the single most common mistake here, because the bed is the one room where nobody can leave the conversation.
16. What does affection look like to you when nothing is expected to follow. A large share of touch in a marriage becomes negotiation, and both people can feel it.
17. When did this part of our marriage feel easiest, and what was different about our life then. Usually the answer is sleep, money or the absence of a small human. Useful to know it was circumstance rather than character.
18. What do you need in the 3 hours before, not the 3 minutes before. This question changes more bedrooms than any other one I ask.
19. Is there something you want that you have never asked for because of how you think I would react. Answering this takes courage and hearing it takes more. Read rule 3 again before you open this one.
20. Do you think the way this has cooled means something is wrong with us. Almost everybody says yes privately, and almost everybody is wrong about why. The mechanics are in how desire fades naturally.
A good question opens a door, and then the two of you are standing in a room you did not plan to be in on a Tuesday. That is the point, and it is why the rules exist.
Matthew W. Hoelscher, PCC
Set five: children, family and everybody else
Most couples have never actually negotiated any of this. They inherited it from the two houses they grew up in and then discovered the terms did not match.
21. What did your parents' marriage teach you about how a husband or a wife is supposed to behave. Nobody escapes this and nobody chose it.
22. Where do you think the line is between our family and our families. Miami is generous with relatives and the line is rarely drawn until somebody crosses it.
23. What is one thing about how I parent that you have wanted to say and have not. Brace, answer honestly, and remember that a criticism about parenting is almost always a request in a bad costume.
24. When we disagree in front of the children, what do you want to happen. Agree on this in advance and you will remove a whole category of Sunday from your life.
25. Who outside this marriage knows the most about our problems, and are you comfortable with that. Every marriage has a third party with an opinion. Most couples have never checked whether they agree on who it is.
Set six: where this is actually going
Couples rarely break because they disagreed about the future. They break because nobody checked for 9 years and then discovered they had been walking at slightly different angles the whole time.
26. What are you quietly hoping our life looks like in 5 years, including the part you think I will not like. The second half of that sentence is the whole question.
27. What have you stopped expecting from me. Not what you want, not what is wrong. What you have quietly given up on. It is a hard question to hear and a harder one to answer, and in my office it is frequently the moment the real session starts.
28. What would you need to see from me in the next 90 days to feel genuinely hopeful about us. Specific, short, achievable. Not a promise about the next decade.
29. What are you most proud of that we built together. End on this if the evening has been heavy. It is not filler, it is a reminder that the two of you have a track record and it is not all in the drawer.
30. Is there anything you have wanted to say during all of this and have not. Ask it last, mean it, and then wait. This is the question that produces the answer the other 29 were setting up.
When to put the list down
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If it turns into a case
The moment either of you starts using answers as evidence, the exercise is finished for the night. Close it, apologize, and come back in a week.
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If one of you is not safe to be honest
If you are managing your answers to avoid a reaction, that is not a questions problem. That belongs with a licensed professional, not with a list on the internet.
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If the same subject keeps detonating
Three failed attempts on the same set is not stubbornness, it is a signal that the two of you need a third person in the room for that specific subject.
Talk it through
If a set went somewhere and you do not know what to do with what came out, that is the normal outcome and it is a good reason to get somebody in the room. If you want to know what actually happens in that room first, I set it out plainly in how to make couples coaching work.
Otherwise, book a free 25 minute call. It is for first timers, it costs nothing, and the only thing I am establishing is whether I am the right person for what came up at your table.
Questions couples ask
Should we work through all 30 questions in one sitting?
No, and I would treat that as the main way this goes wrong. Take one set of 5 per sitting and stop at the end of it even if the conversation is good. These questions open subjects faster than most couples can close them, and a good evening that runs 40 minutes too long usually ends worse than a short one.
What if my partner refuses to do this?
Do not push the list. Pick one question, ask it in the car or on a walk, and do not mention that it came from anywhere. Most refusals are about the format rather than the content. Nobody wants to be handed a worksheet by their spouse, and a single question asked naturally almost never gets refused.
Are these the same questions you use in a session?
Many of them, though in the room I choose them live based on what the two of you are actually doing rather than working down a list. The difference a coach makes is not the questions, it is that somebody is watching what happens between you when the question lands, and stopping the conversation before it becomes the fight.
What do we do with the answers?
Pick one thing, this week, that is small enough to actually happen. Not a resolution about the next 5 years. One conversation, one change, one thing you are going to stop doing for a week to see what fills the gap. Insight without execution is entertainment, and in a marriage it is expensive entertainment.