Controversial Questions to Ask a Guy
For anyone dating a guy who wants to know where he actually stands before things get serious. Twenty questions about who did what in the house he grew up in, money and earnings, children, faith, politics he would not date across, apologising, therapy, privacy and how his last relationship ended. Each one comes with what to listen for, including what a bad answer sounds like.
The questions
Open any question for the note
What is something you have changed your mind about in the last few years?
Why ask it
A gentle opener that still tells you a lot, because it shows whether his views are things he holds or things he inherited. Listen for what changed him: an argument, a person, an experience. A man who cannot name anything usually has not tested his positions against much.
In the house you grew up in, who did what, and how much of that do you want to repeat?
Why ask it
More revealing than asking about gender roles in the abstract, because it starts from something concrete he watched every day. The second half is the real question, and "I have never thought about it" is worth noticing given you will be living inside the answer.
How much time on your own do you need to feel like yourself?
Why ask it
Sets up a difference that causes trouble later if it stays unspoken. Ask for hours and shapes: an evening, a Saturday morning, a weekend away. Someone who claims to need none often withdraws without warning instead.
If one of us got offered a job in another city, how would we decide?
Why ask it
A hypothetical he cannot answer with a slogan. Watch for whether he describes a process the two of you would use or simply assumes whose career leads. Assumptions expressed casually here tend to be exactly how the decision goes when it is real.
How would you feel if I earned significantly more than you?
Why ask it
Ask it flatly and let him answer badly if he is going to. The reassuring script is easy to produce, so listen instead for whether he has ever been in that situation, and how he talks about friends whose partners out-earn them.
If we lived together, how should money work: everything shared, split down the middle, or separate with a joint pot?
Why ask it
Three concrete options are harder to dodge than a question about financial values. Splitting evenly sounds fair and stops being fair the moment incomes diverge or someone takes parental leave, so ask what he thinks should happen then.
At what point should two people tell each other what they earn and what they owe?
Why ask it
Lets you approach debt without demanding a number tonight. A long delay, or an answer that only applies once you are married, sometimes means there is something specific he is not ready to say, and it is better to know that a question exists.
Do you want children, and how sure are you?
Why ask it
The second half matters more than the first. "Probably, one day" from someone in their thirties is a different answer from "yes, and I have thought about when". Vagueness sustained over months is usually an answer rather than an open question.
If we had a child, what would actually change about your week?
Why ask it
This is where stated intentions meet the calendar. Listen for whether he names things he would give up: the gym slot, the away games, the late nights working. If nothing in his week changes in his own description, his plan is that yours does.
Do you believe in anything, and would you want it in a child's upbringing?
Why ask it
Nominal faith and practising faith are very different to live alongside, and the difference often only surfaces at a baptism, a holiday or a funeral. Ask what his family expects too, since that is frequently the real force in play.
Is there a political position that would stop you dating someone?
Why ask it
Turns an argument about politics into a question about limits, which is more useful and less heated. Both a long list and a flat "none" are worth exploring: one may mean rigidity, the other may mean he has never had to hold a line on anything.
What is something you believe that most of your friends would disagree with?
Why ask it
Tests whether he thinks independently or takes the temperature of the room. The content matters less than whether he can hold a position while being disagreed with, which is exactly what he will have to do with you eventually.
Have you ever fallen out with someone over what they believed?
Why ask it
The story shows you his mechanism for disagreement: he argued and stayed, he went quiet, or he cut the person off. Notice whether he can still describe the other person's view fairly, because that is what he will do with yours in a fight.
What would you want kept off the internet?
Why ask it
Covers photographs, your relationship status, your children if there are any, and his location. Mismatches here cause real friction, and the answer tells you whether privacy is something he has thought about or something he will only mention after being annoyed.
When did you last apologise first, and what did you actually say?
Why ask it
Ask for the words. "I said sorry and we moved on" is not the same as "I said I was wrong to speak to her like that." An apology that arrives with an explanation of why he was provoked is the pattern you would be living with.
Tell me about a time you were clearly in the wrong about something that mattered.
Why ask it
Watch for whether the story ends in what he learned or in how it was more complicated than it looked. If the only examples are trivial, that is either genuine self-protection or a real absence of reflection, and both are worth knowing about.
Have you ever talked to a therapist, and what did you make of it?
Why ask it
The verdict matters more than the fact. Dismissal of the whole idea, or contempt for people who go, tends to predict how he will react if you are the one struggling. Having gone and found it useless is a perfectly reasonable answer with a story behind it.
What do you do when you are upset and do not want to talk about it?
Why ask it
Everyone has a retreat, and knowing whether his is the gym, silence, the pub or an evening on his phone lets you read it correctly rather than as a verdict on you. Ask how long it usually lasts and how you would know when he is back.
What did your last relationship end over, and what was your part in it?
Why ask it
The second clause is the whole question. An account in which she was unreasonable and he was patient, with nothing of his own in it, is the strongest signal in this list. Notice too whether he speaks about her with any residual contempt.
What is the hardest thing about being with you?
Why ask it
A serious answer describes something specific he knows about himself, such as going quiet under pressure or being slow to make plans. A charming non-answer, or a joke, tells you either that he has not looked, or that he would rather you found out later.
Asking hard questions without starting a fight
Practical guidance for the conversation itself
Setting it up
- One or two of these per conversation, not a list. Asked in sequence they feel like an interview, and people being interviewed give you the answers they think are correct.
- Pick the moments with natural cover: a long drive, a walk, cooking, late in an evening. Side by side beats face to face for anything difficult.
- Never by text. Written answers are drafted, and the pause before an honest reply is half the information you are looking for.
- Go second only after you have gone first. Say your own view on money, children or time alone before you ask his, and keep it short so it does not read as a position to agree with.
- Decide beforehand what you actually need to know. If you are trying to reach a decision about the relationship, two or three of these matter and the rest are curiosity.
What to listen for
Ask for the last time it happened
Anyone can describe how they handle conflict, money or apologies in principle. "When did that last actually happen?" moves the conversation to something checkable, and a man with no examples has usually given you a theory about himself.
Watch how his answers match his week
Compare what he says about time, money and effort against what he does on an ordinary Tuesday. Stated values are cheap; how he spends a free Saturday is the version you would be marrying.
Separate an unfamiliar view from a warning sign
A traditional answer, a religious answer or a politics you do not share may be perfectly liveable. What is not liveable is contempt: for an ex, for women generally, for anyone who needs help. Note the tone, not just the position.
Notice deflection styles
Jokes, questions turned back on you, and "that's a heavy one for a Tuesday" all mean the same thing: not now. Once is fair. The same topic dodged three times is your answer, and you can say so gently rather than pressing again.
Give the pause room
The considered answer usually comes after five or six seconds of silence. If you fill the gap with a reassuring qualifier, you will get the reassuring reply that goes with it.
How these go wrong
Asking a question you already have a verdict on
If only one answer is acceptable to you, you are not asking, you are testing. He will feel it and adjust. Better to state your own requirement plainly and see what he says about it.
Treating one bad answer as the whole picture
People answer clumsily on subjects they have never had to put into words, particularly about money and feelings. Ask again another day in different words before drawing conclusions, and see whether the second answer is more considered or just better packaged.
Debating instead of listening
The moment you start correcting his answer, you stop learning what he thinks. If you disagree strongly, say so once, briefly, and return to what he was saying. There will be time to argue later, when it matters.
Ignoring what you hear because the rest is good
Answers about children, faith and where you would live are the ones people most often set aside, on the assumption they will change. Treat them as current facts, and notice if you are already privately planning around them.
Pushing past a real limit
Some topics land on grief, abuse, addiction or a family situation he is not ready to open. If he says he does not want to talk about something, take the answer. Continuing is not honesty, and how you handle that moment tells him something too.
Afterwards
What to do with the answers
- 1Say one true thing back. "That is not what I would want, and I would rather know now" keeps the conversation honest without turning it into an ultimatum.
- 2Sort what you heard into three piles: differences you can live with, differences that need a plan, and things you cannot accept. Most of it lands in the first two.
- 3Return to the ones in the middle pile a week or two later, when neither of you is mid-conversation. Second conversations about money and children are almost always more concrete than first ones.
- 4Watch the next few weeks for whether behaviour matches. If he said he apologises first, notice what he does after your next disagreement.
If he asks why you are asking
Answer honestly: you are working out whether this fits, and you would rather do it now than in two years. That is a reasonable thing to want, and how he responds to hearing it is one of the more useful answers you will get.