Deep Questions to Ask Your Boyfriend
For anyone who wants a real conversation with their boyfriend, past the favorite films and into what he thinks and feels. The 103 questions run in six groups: About him, Feelings, About us, Trust and conflict, The future, and Serious ones, which are best kept for a calm evening when neither of you is in a hurry. The notes say when to ask, what a joke or a shrug in reply tends to mean, and how to answer the question yourself.
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The questions
Each question, and why to ask it
About him
What part of your childhood do you think explains the most about who you are now?
Why ask it
He gets to answer at any size: a house move, a sibling, a parent's job. Ask on a long drive or a slow evening, and give your own answer afterwards so it feels like a trade and not an interview.
What were you like at fifteen, and would the two of us have gotten along?
Why ask it
The "would we have gotten along" part keeps it light enough to answer honestly. Notice whether he talks about that boy with affection or with a wince; it's often close to how he talks about his own mistakes now.
Who has had the biggest influence on the man you are, for good or for bad?
Why ask it
Adding "or for bad" lets him name someone he defined himself against, which is how plenty of people work out who to be. If it's a hard person to talk about, a one-line answer is enough for tonight.
What's the hardest year you've had so far, and what got you through it?
Why ask it
What got him through is the half to remember: a friend, work, the gym, plain stubbornness. It's what he'll reach for the next time things are hard, and you'll recognize it when he does.
What are you most afraid of in life, not counting spiders or heights?
Why ask it
Ruling out the easy answers saves you a joke about clowns. Failing, ending up like a relative, being left: whatever he names, don't promise him it won't happen. Ask when he last felt it.
Who in your family are you most like, and how do you feel about that?
Why ask it
The name comes quickly. The feeling about it takes longer and is the real answer, so if he says "my dad" and goes quiet, leave the silence alone for a moment.
What did you have to deal with earlier than most kids your age?
Why ask it
If he says "nothing, really," take that as a true answer and not a dodge; plenty of people had an easy run and feel slightly guilty saying so. When there is an answer, such as money trouble at home or a younger sibling to mind, it often explains why he's the responsible one in the room now.
Which compliment have you never forgotten, and who gave it to you?
Why ask it
A gentle one to place between two heavier questions. The compliment he kept is a hint about what he most wants to be true of himself, so it also tells you what kind of praise from you will mean something.
What do your parents still get wrong about you?
Why ask it
Parents often hold on to a version of their son that is ten years out of date. Where theirs is wrong tells you what he has worked to change, and which family jokes he's tired of hearing.
What were you praised for as a kid, and do you still feel you have to be that person?
Why ask it
A label a boy gets praised for (the smart one, the easy one, the tough one) can turn into a job he never gets to quit. This hands him a way to say he's tired of it, so don't answer with more praise for the same thing.
What do you do when you're alone that makes you feel like yourself again?
Why ask it
Once you know whether it's gaming, a run or driving nowhere with the music up, his disappearing into it for an hour stops looking like distance and starts looking like upkeep. Ask how often he needs it, and whether he's been getting it.
What would a successful life look like to you if nobody else were keeping score?
Why ask it
"If nobody were keeping score" removes the answer meant for his parents or his old classmates. Compare the picture with how his weeks go now, and if there's a gap, ask which part of it he'd close first.
What's a failure that shaped you more than any success did?
Why ask it
He may need a minute, since failures tend to get filed under things not to mention. Listen for whether it comes out as a disaster or as a lesson, then ask what he'd say to someone about to make the same mistake.
What's something you believe about yourself that you'd like to be wrong about?
Why ask it
Usually it's a sentence that starts "I'm just not." Hold off on correcting him. Ask where the idea came from, since it often traces back to one remark from one person.
Do you think people can really change, and what's the biggest way you have?
Why ask it
His general answer tells you how he's likely to hear a promise to do better, yours or his own. The personal part stops it becoming a debate: ask what caused the change, whether a person, a scare or simply getting older.
Do you believe in God, fate or anything bigger than us, and has that changed since you were a kid?
Why ask it
Curiosity is the right spirit here, not checking his answer against yours. Start from the "since you were a kid" end if he stalls: what he believed at ten and when it shifted is a story, and stories are easier than positions. If the two of you differ, tonight is for hearing it, not for settling it.
What do you want from life that you're a little embarrassed to say out loud?
Why ask it
Ambitions get hidden when they seem too big or too ordinary. A laugh here costs you every later answer, so take it seriously, and tell him one of yours.
What's something you've never quite forgiven yourself for?
Why ask it
Save it for a night when you have nowhere to be. Telling him to let it go won't help; asking what he'd say to a friend who had done the same thing sometimes does.
What's something you've told only one or two people, or nobody at all?
Why ask it
Offering "one or two people" lets him choose something medium-sized instead of freezing in front of his biggest secret. "Let me think about it" is a fine answer, and he may come back to it days later. Whatever he tells you stays with you, not with your friends.
Feelings
When something is bothering you, how long does it usually take before you can put it into words?
Why ask it
Some people know within the minute and some need two days, and neither is hiding anything. If he's a two-day person, "I don't know yet" is a complete answer and pushing only slows it down.
What's something you feel often but almost never say?
Why ask it
Don't be surprised if it's a good feeling. "I'm proud of us" can be harder to say than "I'm annoyed." Whatever it is, saying it to you once makes the second time easier.
What does a bad day look like for you from the inside, when from the outside you seem fine?
Why ask it
You get the tells you've been missing: shorter texts, a longer shower, more scrolling. Ask what he'd want from you on a day like that, even if the honest answer is nothing at all.
What makes you feel loved that you'd feel silly asking for?
Why ask it
The silliness is why you've never heard it, and it tends to be small: a hand on his back, a text for no reason, being asked how the thing at work went. Now that you know, do it without announcing that you're doing it.
What do you wish I asked you about more often?
Why ask it
A lot of boyfriends get asked how work is going and not much else. His answer is a standing invitation, so use it within the week, or it will look as if you only asked because a list told you to.
What were you taught to do with sadness when you were growing up?
Why ask it
What a boy was shown, whether that was hiding it, joking about it or keeping busy, is often what the man does by default. It also goes some way toward explaining how he responds when you're the sad one.
When was the last time you felt like crying and didn't?
Why ask it
Easier to answer than "when did you last cry," because he gets to keep his composure in the story. The useful follow-up is what stopped him: who was in the room, or what he thought would happen. Don't tell him he should have.
What's been on your mind this month that you haven't brought up?
Why ask it
Ask when he seems fine, not when he seems off, so it doesn't sound like an accusation. "Nothing" is often true. If it comes with a pause, tell him you're around whenever and leave it there.
What makes you feel like you're doing well as a boyfriend, and what makes you feel like you're failing at it?
Why ask it
He may be keeping a private scoreboard that nobody has ever seen. You might find he's losing points for things you never cared about, which is a relief to both of you once it's said.
Who do you talk to when it's something you can't bring to me?
Why ask it
There should be someone: a brother, a friend, a group chat. That isn't a secret kept from you; it means he has more than one place to put things. If the answer is nobody, that's worth knowing too.
What's something you're insecure about that you think I haven't noticed?
Why ask it
You may well have noticed, and "I know, and it has never mattered to me" lands better than acting surprised. Never bring it up later in a fight. That's the surest way to stop him answering questions like this.
What emotion comes out of you as anger when it's really something else?
Why ask it
Worry and embarrassment have a way of arriving dressed as irritation. If he can name the swap, the next sharp remark in traffic gets easier to read, and you can ask "is this the worry one?" without it sounding like a jab.
When you're happy, how would I know?
Why ask it
It sounds obvious until he tries to answer. Some people get louder, and some go quiet and start fixing things around the house. Learning his version means you stop missing his good days.
What scares you about being really known by someone?
Why ask it
It's a question about closeness itself, so ask when you already feel close. Being found boring and being found needy are common answers. A joke in reply usually means it landed: smile, and give your own answer instead of pressing.
What does being in love feel like to you on an ordinary day?
Why ask it
The word doing the work is ordinary. You're not after a speech, you're after "I save things up to tell you" or "I sleep better." If he says he can't describe it, ask when he notices it most.
What do you still miss about someone who's no longer in your life?
Why ask it
Let him set the depth: it might be a grandparent, a friend who moved away or someone he fell out with. If the person died, you don't need to say anything wise. "Tell me about them" is enough.
What feeling do you avoid, and what do you do to avoid it?
Why ask it
He'll probably recognize the routine before the feeling, because avoiding has habits: overworking, reaching for the phone, staying busy until bedtime. Work back from the habit to what it keeps away. No fixing is needed tonight; noticing is the point.
When do you feel most at peace?
Why ask it
A short answer is fine here, even just a place or an hour of the day. It makes a good close to a heavier conversation because it leaves him thinking about something calm, and it tells you where to take him after a hard week.
About us
What are we good at as a couple that we don't give ourselves credit for?
Why ask it
Begin the relationship questions here, on a strength. Two people who can name what works have something to stand on when the talk moves to what doesn't.
Was there a moment you knew you wanted to be with me, and what was happening?
Why ask it
There's often a specific one: a conversation, a bad day you handled well, an ordinary morning. He may never have mentioned it because it happened quietly in his own head. Have yours ready, because he'll ask.
What's one thing you'd like more of in our relationship, and one thing you'd like less of?
Why ask it
Asking for both makes it a trade and not a complaint. Defend nothing. Pick the smaller of the two and act on it within the week, which is what shows the question was real.
What have I gotten wrong about you that you never bothered to correct?
Why ask it
Maybe you think he hates surprises or loves his job. Small wrong assumptions add up to feeling unseen, and fixing one is oddly intimate. Laugh, update, and ask if there's another.
How has being with me changed you, for better or for worse?
Why ask it
The "for worse" is what makes the rest believable. If he says he's lost touch with a friend or a hobby since you got together, hear it as something the two of you can fix, not as blame.
What do you think I need from you that you find hard to give?
Why ask it
He has to describe your needs in his own words, and he may be more accurate than you expect. If he's wrong, correct him kindly. If he's right, say so and ask what would make it easier.
What small thing would make our ordinary weeks feel closer?
Why ask it
Deep doesn't have to mean dramatic. He might say eating at the table, or phones away after ten. A small, specific answer is the best kind, because you can start on Monday.
What's the biggest difference between us, and is it a strength or a strain?
Why ask it
Couples usually know their difference, tidy and messy or planner and improviser, and seldom discuss whether it helps. If he says strain, ask for an example before you defend your side.
Which memory of us do you go back to most, and why that one?
Why ask it
The reason is the real answer. If it's the day everything went wrong and you both laughed anyway, he's telling you what he thinks the two of you are made of. Tell him yours, and don't be put out if it's a different day.
What did we do in our first few months that you miss?
Why ask it
Early habits fade because life fills up, not because anyone decided to stop. Whichever he names, the long phone calls or the late walks, bring it back in the next two weeks without making a ceremony of it.
What do you wish I understood about the way you show love?
Why ask it
He may be saying it with a full tank of gas and a fixed shelf while you're listening for words. Once he tells you his version, you'll start seeing it in things you had read as ordinary chores.
When I ask what's wrong and you say "nothing," what would you like me to do next?
Why ask it
Sometimes "nothing" means nothing, and sometimes it means "not yet." Have him pick the follow-up that works on him: drop it, come back in an hour, or sit nearby and wait. Then tell him what your own "I'm fine" usually means.
What do you say about us to the person you're most honest with?
Why ask it
Everybody has a friend or a sibling who gets the unedited version. You want the gist, not a transcript. If he hesitates, that's discretion and not guilt, and you can let him keep it.
What does commitment mean to you, in terms of what you actually do?
Why ask it
"Being loyal" is a definition. You're after the behavior: showing up when it's inconvenient, staying in the room for a hard talk. Compare lists, because the gaps between them are where disappointments tend to start.
Is there anything about how we started that you'd do differently?
Why ask it
Most beginnings have a clumsy patch: slow replies, months of not defining it, something said in the first argument. Laughing about it together takes the sting out, and an apology that arrives a year late still counts.
What do you admire about me that you've never said?
Why ask it
Let him finish, and don't bat it away with a joke. How you take this compliment decides how often he tries again. Then give him one back that has nothing to do with how he looks.
What makes you feel like we're a team, and when do you feel like we're on opposite sides?
Why ask it
The opposite-sides half usually involves a recurring situation: his friends, your family, money, plans. Hearing about it as a pattern on a calm day is far easier than discovering it in the middle of a disagreement.
Do you feel you can be completely yourself with me, and where do you hold back?
Why ask it
Almost nobody says "completely" and means it, so don't be stung by the second half. He might tone down his humor, his nerdier interests or his bad moods. Ask what he thinks would happen if he didn't.
Trust and conflict
What does trust mean to you: honesty, loyalty, reliability, or something else?
Why ask it
Two people can both say trust matters most and mean different things. One means "never lie to me" and the other means "do what you said you would." Find out which he's guarding before assuming it matches yours.
What did a fight look like in your house when you were a kid?
Why ask it
His reflex in a fight with you was learned there, whether the house ran on shouting, on icy silence or on a rule that nobody disagreed at all. Yours was learned in your house, so trade answers.
What goes through your head in the first minute after I say "we need to talk"?
Why ask it
For a lot of people that sentence sets off an alarm before anything has been said. If he braces for the worst, agree on a different opening line, one that tells him the size of the problem up front.
After a fight, how long do you need before you can talk about it properly?
Why ask it
Never ask this mid-argument. Ask on a quiet day, so the answer is a plan and not a defense. If he needs an hour and you need it settled before bed, you've found the real cause of several fights.
How do I react to bad news or criticism, honestly, and does it ever make you hold things back?
Why ask it
This one is about you, so brace a little. If he says you get defensive or go cold, the only useful reply is "thank you for telling me." Anything else proves his point.
Have you ever been cheated on or lied to in a way that still affects you?
Why ask it
Ask once, and not as a way of opening a talk about your own worries. If the answer is yes, his caution or his need for reassurance has a history that isn't about you. How much detail to give is up to him.
Where is your line between privacy and secrecy in a relationship?
Why ask it
No single answer is the correct one, but two lines that are never compared will collide eventually, usually over a phone, a password or what gets told to friends. Say where your own line is before reacting to his.
What counts as cheating to you?
Why ask it
A serious question that sounds too obvious to ask. People differ on texting an ex, on flirting and on keeping something hidden, and couples tend to find the difference the hard way. Ask it as a definition, on a day when nothing prompted it.
Who gave you the best apology you've ever had, and what did they get right?
Why ask it
He's telling you what a real apology sounds like to him: the words, a changed habit, a gesture. Remember it, since "I'm sorry" in your style may not register in his.
Do you find it harder to apologize or to forgive?
Why ask it
He'll likely know which at once. The follow-up is what makes it hard: pride, fear of it being held against him, or not being sure it's really over. Whichever he picks, you now know which half of making up to do the heavy lifting on.
Is there anything from an old argument of ours that still isn't settled for you?
Why ask it
A fight can end without being finished. If something comes up, don't argue it again. Ask what would close it for him, and be prepared for the answer to be as small as an acknowledgment.
If I were ever unhappy with us, would you want me to tell you straight away or wait until I was sure?
Why ask it
It reverses the usual direction and shows how he takes hard news. Most people say "straight away" and then flinch when it comes. Agree on it now and you have a small contract you can both point to later.
What's a topic where you feel like you can't win with me?
Why ask it
Expect something specific: his driving, his mother, the way he tells a story. If he can't win, he has probably stopped trying, and that deserves more of your attention than the topic does.
What makes you jealous, even when you know it shouldn't?
Why ask it
The last clause lets him admit it without having to defend it. Don't use the answer to talk him out of the feeling, and never to test it later. Ask what helps when it shows up: hearing about plans in advance, meeting the person, or just being able to say so.
What's a promise you've broken that you still think about?
Why ask it
It doesn't have to be a promise to you, or to any partner. Whether he tells it with excuses or without is a fair preview of how he treats his word. Don't ask it as a trap, and offer one of your own.
What do you need from me to feel sure I'm on your side, even when I disagree with you?
Why ask it
Disagreement and disloyalty can feel identical in the moment. He might say "don't correct me in front of people" or "start with the part you agree with." Small rules like those keep one argument from becoming a question about the whole relationship.
Is there a small lie you tell me to keep the peace?
Why ask it
Asked with a smile, it gets a real answer, most often "I'm fine" or "I don't mind." The small ones matter because they teach you both that smooth is worth more than accurate. Own up to one of yours.
The future
What kind of father do you think you'd be, and what worries you about it?
Why ask it
It works whether or not he's sure he wants children, because it's about him and not about a plan. The worry is the part to listen to, and it's often a sentence about his own father. This is not the night to settle the question of kids.
What do you want our life to look like that's different from how you grew up?
Why ask it
People build their adult lives partly as a correction: more time at home, less worry about money, a louder house or a quieter one. Give yours too, and see whether the two corrections fit under one roof.
What's a goal you've gone quiet about because you weren't sure I'd take it seriously?
Why ask it
Goals get shelved when the first mention earns a raised eyebrow. If the eyebrow was yours, say so, and ask him to tell you about it again from the start, whether it's a business idea, more school or a move.
What do you hope is different about you in ten years, and what do you hope stays the same?
Why ask it
"Different" tends to bring out patience, money or health. "The same" is the rarer half: it makes him say what he likes about himself today, which he may never have said to anyone. Tell him what you'd keep about him too.
What part of committing for the long term makes you nervous?
Why ask it
Nerves are not a no. Losing his independence, repeating his parents' story, money: a named fear can be planned around, while an unnamed one comes out as stalling. Add what makes you nervous so it's a shared list.
What would you need to feel sure of before you'd want to marry someone?
Why ask it
Saying "someone" takes the pressure off the two of you while still telling you a great deal. If his list is already true of you both, he'll notice as he says it. You don't need to point it out.
How would you know we were ready to live together?
Why ask it
Listen for the practical conditions (his own income, a lease ending, what his family would say) separately from the feeling, because a list of conditions is not a no. If you already share a place, ask what he'd do differently about how you got there.
What's your biggest worry about money, and how much of it have you told me?
Why ask it
Money worries tend to come with shame, so he may hand you a small piece first: a debt, a salary he thinks is too low, family he helps support. Thank him for the piece. The rest follows when the first part is received without alarm.
Which of your family's traditions would you carry on, and which would you quietly retire?
Why ask it
A lighter question for this group. Whether he keeps the Sunday dinners and drops the holiday that always ended in a fight shows you what family feels like to him when it's going well.
Whose relationship do you look at and think, that's what I'd want?
Why ask it
Who the couple is matters less than what he sees in them: the teasing, the calm, the way they back each other in public. That detail is his working definition of a good partnership, so ask for it.
Is there anything you're waiting on before you feel ready to plan further ahead with me?
Why ask it
Some people hold off on planning until they feel they have something solid to offer: a promotion, a debt paid off, a degree finished. Knowing the milestone turns a silence into a timeline.
How would we handle a long stretch apart, if work or family ever required it?
Why ask it
Hypothetical for most couples, which makes it safe to explore. You learn how much contact he needs to feel close, and whether distance reads to him as a test or as a threat.
What do you want our relationship to never turn into?
Why ask it
He'll probably describe a couple he has seen: the pair who sit in silence at restaurants, or who snipe at each other at parties. A shared picture of what to avoid gives you both a phrase to use when you see it starting.
If we had children one day, what would you want them to learn from watching the two of us?
Why ask it
It moves the subject of kids away from yes or no and toward the kind of home he has in mind. If children aren't in his plans, swap in "anyone watching us" and the question still works.
What decision about our future would you want us to make on purpose instead of letting it just happen?
Why ask it
Couples slide into a lot: a shared lease because one ran out, a city because of one job. He may name something you've already begun sliding into, which is your cue to stop and choose it together.
Serious ones
Are you happy with us right now, honestly?
Why ask it
Ask on a good, ordinary day, and wait out the pause. "Yes, mostly" is a healthy answer, and the "mostly" is your follow-up. Never ask it as a challenge during a fight, when every possible answer is a bad one.
Is there anything about me you're hoping will change with time?
Why ask it
If there is, better to hear it now than to discover he's been waiting. Some hopes are fair, like being on time. Hoping for a different personality is another matter. Tell him plainly which things are likely to change and which aren't.
What do the people closest to you really think of us?
Why ask it
He may soften it, and you can let him. What you're after is whether he'd stand beside you if there were friction with his family or friends, or expect you to earn your way in alone.
Is there anything in your past that you think I should know before we get more serious?
Why ask it
Make it clear he doesn't have to answer tonight. People sit on things like a debt, a health matter or a rift with family until they're sure of the reception, and a door left open often gets used later, at a time he picks.
Is there anything you've gone along with for my sake that you didn't really want?
Why ask it
It could be a plan, a pace or a whole weekend routine. Going along now and then is kindness; as a habit it tends to turn into a grudge that neither of you can date. If he names something, don't apologize it away. Ask what he'd have chosen.
Do you think the two of us want the same kind of life, and where are you least sure?
Why ask it
"Where are you least sure" is what makes it answerable. Children, where to live, how much ambition a life should hold: better to find the uncertain spot together than to assume it away. It doesn't need resolving in one sitting.
What have you put up with in a relationship before that you never would again?
Why ask it
Deal-breakers learned from experience are firmer than ones borrowed from a list. He's also telling you what went wrong before, from his side. Treat it as information about him and not as a warning aimed at you.
When things between us get hard, what makes you want to stay and work at it?
Why ask it
Whatever he says is the thing he holds on to, so it's worth hearing in his exact words. "Because it's you" is lovely. "Because we always manage to talk in the end" is sturdier. Give him your reason too.
What would you want us to do if we hit a problem we couldn't sort out between the two of us?
Why ask it
You're finding out whether asking for help, from an older couple you both trust or from a counselor, would feel to him like good sense or like defeat. That's far easier to agree on now than in the middle of the problem.
Is there something you need from a partner that you're not sure I can give?
Why ask it
The hardest question in the group, and not one for a tired evening. If he names something, don't promise on the spot. Ask what it would look like in practice, and take a few days before saying what's possible.
How do you feel about how fast or slow we're moving?
Why ask it
A mismatch in pace is common and rarely means one person cares less. If "fine" comes too quickly, go first with your own honest answer. People often wait to hear which way it's safe to lean.
When you're at your lowest, what does it look like, and what should I do or not do?
Why ask it
Pick a steady day for this. Some people want company, and others want a text now and then and otherwise to be left alone. If what he describes sounds heavier than a rough patch, it's fine to ask whether he has ever talked to anyone about it.
What comes before our relationship for you right now, and do you expect that to change?
Why ask it
An honest ranking is not an insult. If work, a family obligation or getting back on his feet comes first for now, you're asking so you know what you're signing up for, and whether the order is temporary or permanent.
Where do you see the two of us in five years, in as much detail as you can manage?
Why ask it
Only ask if you can hear "I haven't pictured it yet" without panicking; early on that's an honest answer. The detail is what counts: a city, a kitchen, what a Saturday looks like. Describe your own picture second, so he isn't just agreeing with it.
If you ever started pulling away from me, what would it look like, and what would you want me to do?
Why ask it
He's describing his own warning signs while nothing is wrong: fewer plans, shorter replies, longer hours somewhere else. Later you can say "you told me about this once," which is much easier to hear than "what's going on with you?"
What question have you been hoping I'd ask you?
Why ask it
Keep it for last. He may hand you the conversation he's been waiting to have, or shrug and say he's been asked plenty. In both cases, pass him the list and let him choose one for you.
How to have a deep conversation with your boyfriend
Practical guidance for the conversation itself
Before you ask anything
Pick a time with nothing after it
Deep questions need slack. Ask on a walk, a long drive or a slow evening at home, not in the ten minutes before his shift or when either of you is hungry. If you'd have to cut his answer short, wait for another day.
Tell him why you're asking
A serious question out of nowhere can sound like the start of bad news. One sentence fixes it: "Nothing's wrong, I found some questions and I'm curious about you." He'll answer more freely once he knows he isn't in trouble.
Never during an argument
Every question in the Trust and conflict and Serious ones groups turns into a weapon when it's asked in the middle of a fight. "Are you happy with us?" is a real question on a calm Sunday and an accusation at midnight. If you're angry, the list stays closed.
Match the group to how long you've been together
About him and Feelings work from the first month. About us needs some shared history to draw on, and The future and Serious ones assume you've been together long enough that the answers matter to both of you. Asked in week three, "Where do you see the two of us in five years?" is pressure, not curiosity.
Start one level below where you want to end
Open with something from About him, where the answers are stories and nothing is at stake between you. Move to the relationship once he's talking easily. Two or three questions make a full evening, and the rest will still be here next week.
Reading what comes back
He makes a joke
Humor is how plenty of people buy a few seconds with a question that hit home. Enjoy the joke, then stay quiet a beat longer than usual, because the real answer often follows on its own. If it doesn't, the subject is tender and can wait for another week.
He says he doesn't know
Believe him. Some of these are questions nobody has put to him before, and a first answer takes time to form. Say there's no hurry, drop it completely, and don't be surprised if he raises it himself later in the week.
He turns it back on you
"What about you?" can be a dodge, or it can be him wanting to see how honest the answer is supposed to be. Go first, and be as open as you're hoping he'll be. Then ask him again.
He says something you didn't want to hear
That's the list working. Thank him before you respond, keep your voice where it was, and ask one question to understand it better. You can disagree tomorrow. If honesty costs him an argument tonight, he'll stop offering it.
Your half of the conversation
Answer what you ask
Plan to answer every question yourself, and say so at the start. A conversation where only one person is exposed is an interview. Your answers also show him how deep you mean to go.
Don't keep a file
Anything he tells you here stays out of future arguments and out of the group chat. The first time an insecurity he confided comes back at him in a fight is the last time he confides one.
Leave some things unfinished
A serious question doesn't have to end in a decision. If you find a real difference about marriage, children or money, you've done the evening's work by finding it. Agree on a day to come back to it and let the night recover.
Text or in person
Most of About him and Feelings work over text, where he has time to think and nobody is watching his face. Keep Trust and conflict and Serious ones for when you're in the same room: tone goes missing on a screen, and a slow reply reads as something worse than it is.