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50 Hypothetical Questions to Ask Your Mom

50 hypothetical questions to ask your mom — what-ifs that reach the woman who existed before the role, and the arrangements nobody ever put to her.

By Endearist 50 questions

You met your mother already assembled. Everyone else in her life — her sister, her school friends, the woman she worked beside at twenty-three — met a person first and a mother later, if at all. You got the finished thing, and most questions you can ask her only confirm it: they invite her to describe the role from inside the role. A hypothetical does something no direct question can. It takes the arrangement she has lived inside for decades and, for the length of one sentence, un-assumes it. These fifty are built around four things that are almost unaskable straight out: the jobs that were never assigned to her because nobody ever proposed them, the young woman you were never introduced to, the wanting she only ever does on somebody else's behalf, and the fact that she is the one person alive who has watched this particular job done twice — once as a child and once as a mother.

The arrangement nobody ever proposed

Very little of how her days were divided was ever decided. Nobody sat down and allocated the phoning, the remembering, the noticing, the staying home; it simply landed, and because no decision was taken there is nobody to be angry with — which is precisely why it cannot be raised straight out. A what-if un-assumes it for one sentence. It lets her say what she would have picked without anyone having to be accused of picking it for her.

  1. If someone had sat you and my father down at the start and asked, properly, which of you was better suited to be the one at home — what would the honest answer have been? Listen for whether she answers about suitability or about what was possible. If she cannot separate the two, that is the finding, and it is worth saying out loud that nobody ever asked.
  2. If the jobs in this house had been dealt out at random by somebody who knew neither of you, which one would you have been sorry to lose? This separates the load from the parts she was attached to, and it blocks the tidy answer that all of it was a burden. Expect one surprising keeper.
  3. If you had been paid the going rate for everything you did here, what would have been on the first invoice that we would have argued about? The argument is the point. Whichever item she expects you to dispute is the work she believes nobody in this family ever counted as work.
  4. If somebody else had been the one who remembered the birthdays, rang your mother-in-law and knew where everything in this house was — who would it have been, and would it have got done? Most women name a person and then answer no. Ask what would have gone wrong first; the reply maps everything that stayed invisible because it never once failed.
  5. If moving for work had always meant moving for yours, where would this family have ended up living? Ask for the town, not the feeling. A specific place makes the counterfactual solid enough to keep walking around in, and the story of why that town usually comes free.
  6. If nothing at all had been assumed about who does what, which of the things you ended up doing would you have put your hand up for anyway? This is the kind version of the whole group: it gives her back the credit for the parts that were genuinely hers. Do not rush past the list.
  7. If we had all had to write down at the time who was responsible for what, do you think anyone would have signed their name under your list? The signature is the mechanism: an unwritten arrangement is one nobody has to own. If she laughs, ask who would have crossed items out.
  8. If you could have gone on strike for a week and nobody would have been harmed by it, what would have fallen over first? The no-harm clause is doing the work; without it she will not play. Whatever falls over first is the thing she has held up longest without anyone noticing.
  9. If a stranger had watched one ordinary Tuesday in our house back then and had to guess who was in charge, who would they have said? Ask a second time for who was actually running it. When the two names come out different, you have the whole arrangement in a single sentence.
  10. If it had been completely unremarkable for a woman to do the opposite of what you did, would that on its own have been enough? Mothers answer this far more precisely than the version about society in general, because it names a permission rather than a climate. A no is not a defeat — ask what else would have had to change alongside it.
  11. If the arrangement had actually been put to you as a proposal — in words, with a yes or a no at the end of it — would you have said yes? This is the centre of the group and it takes a while. Whatever she answers, the thing to notice is that she is answering it for the first time at the age she is now.
  12. If the years when everything ran through you had been split evenly with somebody, what would be different about you now — not about your week, about you? The correction at the end is essential; without it you get a timetable. What she names is usually a capacity she believes she lost rather than an activity she never got to.
  13. If you could hand one standing job to somebody else today — one nobody has ever relieved you of — and never take it back, which one goes? Expect a long pause and then something small and specific. The never-take-it-back clause is what stops her choosing something she would quietly resume by Thursday.

The woman you were never introduced to

Ask her what she was like at twenty-two and you get a summary she has given a hundred times. The way past it is to stop asking her to describe that woman and start putting her in situations instead — beside you, in your flat, in an argument with the person she became. Tested rather than recalled, the young woman turns up with opinions, and some of them the woman she is now does not share at all.

  1. If your twenty-two-year-old self had to share a flat with me for a month, which of us would move out first? Play it for laughs and then ask what specifically she would not have put up with. That list is the portrait of a person, not of a mother.
  2. If I could have been at one party you went to before you had children, which one — and would you have let me stay? The second half gets answered honestly and tells you what she thinks that evening was actually like. Ask who else was in the room.
  3. If she walked into this room right now, what would she notice before she noticed you? Keep the pronoun. Talking about her younger self in the third person is what lets a mother be unkind about her, and the detail lives in the unkindness.
  4. If I had to pack a box that would explain her to somebody who never met her, which three things of hers go in? Objects get past the summary. Ask what became of each of the three; at least one was given away for a reason she still remembers exactly.
  5. If she could see one single photograph from your life now, which one would reassure her and which one would frighten her? Two answers, and the second is the one to wait for. What frightens the young woman is rarely a hardship; it is usually something ordinary she had sworn to avoid.
  6. If she had to introduce herself at twenty-two to a room of strangers, without mentioning her work, her family or where she was from, what would she have said? The prohibition removes every answer she has ready. If she stalls, offer your own bad attempt first — nobody can do this one cold.
  7. If she had been the one raising me instead of you, what would I have got away with, and what would I not have? One of the very few questions that lets a mother criticise her own parenting at no cost, because the critic is herself. Take the second half without flinching.
  8. If she had a vote on one decision you are facing right now, which one would you actually let her have? This asks whether she still trusts her own judgement from back then, which is a thing no mother is ever asked. If she will not give her a vote anywhere, follow that up gently.
  9. If I had been shown one week of her life without being told whose week it was, what would I have got wrong about her? Here she corrects you in advance, which is much easier than correcting you afterwards. What she names is usually something somebody assumed at the time and she never got to answer.
  10. If the two of you disagreed about something today, who would win — and who should? The gap between the two answers is where she tells you whether she thinks she grew up or simply gave in. Do not offer an opinion; she has been waiting forty years for a verdict and yours is not the one she needs.
  11. If you had never had children at all, who would know you best today? Not a question about whether she wanted us; a question about which closeness the children absorbed. Ask whether that person is still alive and still reachable.
  12. If you could keep one thing she had that you no longer have — not a possession, something about her — what are you taking? Ruling out possessions is what makes this hard and worth asking. Whatever she names, ask when she noticed it had gone; most women can date it to a year.
  13. If she had been allowed to write you one letter to be opened at the age you are now, what would she have got badly wrong? Asking for the error rather than the advice keeps this clear of sentiment. What the young woman could not have foreseen is a short description of everything that happened since.

Wanting with nobody on the other end

She has spent decades wanting things for people. The machinery is so well practised that a want with no recipient barely registers as one, and asking her plainly what she wants tends to produce something useful for the household. So none of these leave the proxy route open: the gratitude is blocked, the beneficiary removed, the money forbidden to be spent on anyone else. Whatever is left over is hers, and watching how uncomfortable it gets is half the answer.

  1. If I gave you a whole day and the only rule was that nothing you did could benefit anyone in this family, what would the hard part be? What is being asked for is the difficulty, not the plan. If she answers with errands she would have run anyway, that is the answer, and she can be told so kindly.
  2. If I asked what you wanted for dinner and you were not allowed to say "whatever you're having", how long would it take you to answer? Time the pause out loud and make a joke of it. The length is the measurement: a want that takes eleven seconds to locate for dinner will not be quicker about anything larger.
  3. If you could be bad at one thing without anyone minding, which would you drop tomorrow? Competence is the currency she has been paid in, so this reads as a rare permission rather than a complaint. Ask who exactly she thinks would mind.
  4. If wanting something meant admitting out loud that you had not got it, which want would you still say? For a lot of women it is the admitting, not the wanting, that has been avoided for decades. Do not respond by offering to arrange it; that turns her answer into a task.
  5. If I were not allowed to thank you for anything for a whole year, what would you want from me instead? Gratitude is the currency that lets everyone avoid the real transaction. Blocking it for a year is the fastest route to what she has actually been short of.
  6. If you had to spend a serious sum within a week and could not spend a cent of it on anyone else, at what point would it start to feel uncomfortable? Watch for the figure at which the discomfort starts. That number, not the shopping, is the budget she has quietly been granting herself for years.
  7. If you asked for something and it was simply given to you, with no discussion at all, what would you suspect? Women who have had to justify every request develop a reflex that reads easy agreement as a trap. If she says she would suspect nothing, ask when that stopped being true.
  8. If nobody would ever find out that you had done it, which of the things you keep refusing would you say yes to? This separates a genuine preference from a performance she has kept up so long it is hard to tell apart from the inside. She may need telling that it is not a trick question.
  9. If you had to book something for yourself six months from now, today, and it could not be cancelled, what are you booking? The no-cancelling clause is the entire question; a cancellable plan is one she would give away by the second week. Then offer to book it, and mean it.
  10. If somebody could take one worry off you permanently, but you would never be told which one they took, would you let them? A hesitation here is not about missing the worry; it is the suspicion that her worrying is what keeps everyone safe. That belief is worth naming out loud, once.
  11. If you were told you would be completely looked after for the rest of your life, with nothing at all required of you, how long before you wanted the job back? Almost every mother names a length of time, and it is usually shockingly short. Ask what she would miss first: being needed, or being the one who knows how.
  12. If the only way I could give you something you actually want was for you to tell me what it is, would you tell me — or would you pick something easier for me? Most mothers admit to the substitution, and the admission is the thing worth having. Promise nothing in the moment; come back a week later and ask again.

The only person who has seen this job done twice

This job was done to her, and then she did it, which makes her the only witness in the family holding both ends of it. Ask her about her mother directly and you get either loyalty or a grievance, both settled long ago. Swap the two women instead — give her mother the washing machine, the money and the choices, or put them both on the same street with small children — and the loyalty and the grievance have to be recalculated on the spot.

  1. If your mother had been handed the advice people give new mothers now, which bit would she have thrown straight out — and would she have been right? The second half stops this being a joke at the older woman's expense. A mother who concedes one point to her own mother here will usually concede several.
  2. If she were in the room when you and I disagree, whose side would she take? A grandmother gets claimed as an ally by both parties and asked by neither. If she says her mother would take your side, ask whether that already held when you were fifteen.
  3. If I filmed you for a week without telling you, which of her habits would turn up in the footage? Observed rather than remembered, which gets past the ones she has already made her peace with. Offer the two you have noticed and she will trade you a third.
  4. If she had had what you had — the money, the choices, the machine that does the washing — which of the things you swore you would never repeat would have stopped on its own? This asks whether what she resented was her mother or her mother's circumstances, and it is the kindest form the question takes. Expect one item she insists no amount of money would have touched.
  5. If the two of you had been mothers at the same time, on the same street, would you have asked her for help? The answer tells you whether her mother was a resource or a court, which is the single most useful thing to know about how she was raised. If it is no, ask what she would have pretended instead.
  6. If your mother had had to take on one week of your job as a mother, which week would have finished her? This lets her state what she survived without it sounding like boasting, which she will not do if asked directly. Take the week seriously and ask what was going on in it.
  7. If your grandmother, your mother and you had to agree on one rule for me, what would survive all three? Three generations is a tight enough sieve that only something real gets through. Ask what each of them would have vetoed; that list is longer and far more revealing.
  8. If your mother could see how I turned out, which part would she take the credit for? Notice whether she grants her mother the credit generously or reluctantly, and whether it is a part she would claim herself. Two women are being measured and only one is in the room.
  9. If the line stopped with you — if nothing at all were passed on from here — what would actually be lost? Mothers usually name something far smaller than the family assumes, and it is rarely a tradition. Whatever it is, ask whether she was given it or built it herself.
  10. If the thing you were sure you had broken turned up in me anyway, what would it be? This is the fear she has kept furthest from you, and it is usually a temper, a silence, or a way of leaving a room. Say plainly whether you recognise it; the not knowing is worse for her than the answer.
  11. If your mother had ever said out loud that she was not managing, what would you have done with that at fifteen? Underneath sits the question of whether the silence protected her or cost her, and she has an answer nobody has ever asked for. It usually explains what she did and did not tell you.
  12. If I could ask your mother one question and be certain of an honest answer, what do you hope I would ask — and what do you hope I would not? End here. The second half is the only place in the set where she gets to name something she would rather stayed unknown, and naming it is usually enough on its own — you do not have to go looking.

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What to do with the answers

The most honest answer you'll get tonight is gone in three months unless you write it down. Endearist keeps it — per person, end-to-end encrypted, with a cadence reminder so you can pick the thread back up next time without scrolling through your messages.

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Frequently asked

Won't hypothetical questions just make my mom defensive about the choices she made?

They do when the hypothetical is really a verdict, which is what "would you do it differently" amounts to. Most of these are built so there is nothing to defend. A whole group starts from the position that no choice was ever put to her — that the phoning, the remembering and the staying home were never decided, only assigned by default — so there is no decision to justify and nobody to blame for having made it. The rest block the audit another way: they ask what she would have volunteered for anyway, what a stranger watching would have concluded, which job she would have been sorry to lose.

My mom turns every question back to me. How do I stop that?

Not by asking harder — the reflex is decades old, and it is not evasion but the skill she has had least practice at. Give her a running start instead: answer each question yourself first, at length and badly. A mother who has just listened to a full, unimpressive answer gives a fuller one; a mother who has just had a question fired at her asks whether you are eating properly. It also helps enormously to do this while something else is going on — a drive, a kitchen, a walk — and to take four or five questions across an afternoon rather than working down a list.

Isn't asking "what if you'd never had children" a cruel question?

It would be, if what it asked was whether she wanted us. It does not. The version here asks who would know her best today, which is a question about closeness rather than regret, and the honest answer is usually a sister, a friend from work, or somebody she has not spoken to in twenty years. Children absorb an enormous amount of a person's intimacy, and almost no mother has ever been asked where that intimacy would otherwise have gone. If she does hear it as the other question, say plainly which one you meant and move on — do not argue the point.

How are these different from the questions about her childhood or her dreams?

Those ask her to remember; these ask her to reason, and the two produce very different material. A memory has a set version — she has told the story of her twenties often enough that it has hardened, and that is the version you will get. She has never once had to say what her own mother would have stopped doing if she had had money, or which household job she would have volunteered for if nothing had been assumed. There is no polished answer to those, so you get the first draft. It also means these still work when recall has started to be unreliable, which memory questions do not.

How many of these should I actually use in one go?

Four or five, and not in order. The four groups are separate instruments rather than a sequence: the first un-assumes how the household was divided, the second goes looking for the woman you were never introduced to, the third blocks her habit of wanting things on other people's behalf, and the fourth swaps her with her own mother. Pick the group that suits the day. If one lands badly, drop it and do not return to it in the same conversation — but do come back to it once, weeks later. Mothers answer the second time far more often than the first.