Hypothetical Questions to Ask Your Girlfriend
53 hypothetical questions to ask your girlfriend, for the evening you want a good what if question and not another report on how the day went. They sit in five groups, in the order the conversation tends to go: light what-ifs, her life now, looking back, the two of you, and your future together. The light group asks nothing about the relationship, so those are also hypothetical questions to ask a girl you have only just started seeing.
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The questions
Each question, and why to ask it
Light
What if you were handed a plane ticket that had to be used this weekend? Where would it take you?
Why ask it
The deadline rules out the dream trip that needs a year of planning and leaves the place she can picture herself in by Saturday. If it turns out to be within reach, write it down.
If you were given a small shop on a quiet street and could sell only one thing, what would the shop be?
Why ask it
A bookshop, a bakery and a plant shop are three different daydreams about how a working day should feel. Get the name of the shop out of her, and who she would hire first.
If you could eat one meal again for the first time, which meal would it be?
Why ask it
This is a story more than a menu: where she was, who cooked, who else was at the table. A meal that could be made again at home is a date idea she has just handed you.
What if you woke up tomorrow able to do one thing brilliantly? What would you pick?
Why ask it
Notice whether she picks something done alone or something done in front of a room. Painting, public speaking and cooking point to quite different things she wants more of.
If you could step into any film or book for one day, which one would you walk into?
Why ask it
Find out who she would be once she got there: the lead, a side character, or someone watching from the back of the room. An adventure and a cosy village are two different kinds of day off.
If you could live anywhere for a year, where would you go?
Why ask it
A year rather than forever pushes her past the postcard answer into practicalities: language, work, and who she would miss while she was gone.
If you had to enter a talent show next month, what would your act be?
Why ask it
Four weeks is long enough to practise, so her act is something she privately suspects she could pull off. Volunteer as the assistant and see what job you are given.
What if you could have one superpower, but only a small, everyday one? What would it be?
Why ask it
Keeping it small takes away the saving-the-world answer and leaves the bit of friction she would most like gone from her week: the commute, the queue, the alarm clock.
If your phone could keep only three apps, which three would stay?
Why ask it
The sensible list and the honest list rarely match, and she will know it. It travels well as a text, since she can look at her screen before she commits.
If you had to give up either travelling or eating out for good, which would go?
Why ask it
Both are treats, so she has to decide which one she would actually miss on a grey Wednesday. Ask which trip or which restaurant she pictured while she was choosing.
What if you could spend one day in any year of history and be home by bedtime? Which year would you visit?
Why ask it
Being home by bedtime makes it a visit and not a move, so she is free to choose somewhere uncomfortable. Find out whether she is going for an event, a person, or only to see what her own street used to look like.
What if you could find out one thing about your own future? Would you look, and what would you check?
Why ask it
Some people would look straight away and others would rather not know, and both are answers. What she would check, a job, a city, a person, tends to be the thing she is least sure of this year.
Her life
If you could design your ideal week from scratch, what would be in it?
Why ask it
Listen for what is missing from the week she describes as much as for what is in it. The distance between that week and her real one is often small enough that the two of you could close part of it.
If money stopped being a consideration, what would you do with your time?
Why ask it
More useful than asking about a dream job, since not everyone wants a job at all. Silence here often means nobody has asked her in years, so wait it out.
If you could try a completely different job for one month, with your own kept open for you, which would you try?
Why ask it
The safety net is the point: with nothing at risk she can name the work she is curious about and skip the sensible answer. Then ask what she guesses the worst hour of that job would be.
If you had to teach a class on something you know well, what would it be?
Why ask it
People underrate what they know, so expect a pause and then a subject you had not thought of. Ask for the first lesson on the spot; being asked to explain your thing is a pleasure.
If you could hand one task in your life to someone else for good, which one would go?
Why ask it
You are hearing what wears her down, and it is seldom the thing she complains about loudest. If it is something you could take on now and then, do it next week without announcing it.
If you could move one person you love into the house next door, who would it be?
Why ask it
She is naming the person she misses in an ordinary week, who is not always the person she mentions most. It also tells you whose visits are worth making an effort for.
If this year of your life were a chapter in a book, what would the chapter be called?
Why ask it
A title makes her pass a verdict on the year, which a plain 'how is it going' never gets. Then ask what she would like the next chapter to be called.
If you could be braver about one thing this year, what would it be?
Why ask it
Framed as courage and not as a goal, it finds the thing she has already decided she wants and keeps putting off. Hold back the pep talk and ask what would make the first step smaller.
If someone offered to tell you what people say about you when you are not there, would you listen?
Why ask it
A yes or no with a reason attached. It shows how much she is carrying about how she is seen, and whether she suspects there is something to hear.
If you could get an honest answer from anyone about anything, who would you ask and what?
Why ask it
Whoever she names, a parent, an old boss, a friend who went quiet, the question has probably been waiting longer than she has known you. Resist guessing the answer on that person's behalf.
If you could stop worrying about one thing overnight, what would you drop?
Why ask it
Dropping it overnight is a fantasy, which is what lets her name the worry without having to ask for help with it. Thank her for telling you, and leave the fixing for another day unless she asks.
Looking back
If you could relive one ordinary day from your childhood, which would you pick?
Why ask it
Ruling out birthdays and holidays gets you the routines and people who shaped her, which almost never come up in normal conversation.
If you could keep only five photographs from your life, which five?
Why ask it
Five is too few for every milestone, so a graduation or a birthday loses its place to a blurry picture of nothing much. Get her to find them on her phone while you talk.
If you could thank one person who has no idea how much they helped you, who would it be?
Why ask it
It is as likely to be a teacher, a coach or a friend's parent as anyone in the family. If that person can still be reached, the kind follow-up is whether she would ever send the message for real.
If you could send one sentence back to yourself at fifteen, what would it say?
Why ask it
The sentence is nearly always a reassurance or a warning, and which of the two shows how she remembers being fifteen. See whether she thinks that girl would have listened.
If you could keep one tradition from the family you grew up in and drop another, which would they be?
Why ask it
Half of her answer is nostalgia and the other half is a quiet statement of what she means to do differently. It is good to know both well before the two of you have a holiday to share.
If you had never left the place you grew up, or had left it years sooner, how do you think you would be different?
Why ask it
It works whichever way her life went, because she has to picture the version of herself who took the other road. Notice whether she talks about that person with envy, with relief, or with a kind of fondness.
If you could undo one decision from the past five years, which would you undo?
Why ask it
The five-year limit keeps it to decisions she still lives with. Notice whether she names something she did or something she never got round to doing.
If you could spend one more afternoon with someone you no longer see, who would it be?
Why ask it
It could be a grandparent, a friend who moved abroad, or someone she fell out with. Let her say which without guessing, and then ask what the two of them would do with the afternoon.
If you could skip the hardest year you have had, but lose whatever it taught you, would you?
Why ask it
She has to name the year before she can answer, and that year may explain a reaction of hers you have found confusing. Whether she would skip it shows how settled it is, so listen and hold back the reassurance.
If someone in your family could finally say the one thing you have always wanted to hear from them, what would it be?
Why ask it
She may need a minute, and she may decide not to answer, which is fine. What she is still waiting for, an apology or a plain 'well done', often explains how she takes praise and criticism from you.
The two of us
If you could change one thing about how we spend our weekends, what would you change?
Why ask it
Weekends are small enough to change by Saturday, which makes this a far easier way to hear a real request than asking whether she is happy. Take the first thing she says at face value and try it.
If we swapped lives for a week, what would you change about mine?
Why ask it
Under the game is her honest view of how you run your days: the sleep, the job, the friend you never ring back. Laugh first and argue with none of it.
What if we went on a game show as a team? Which round would you leave to me, and which would you take yourself?
Why ask it
The round she hands you is a compliment she might never pay you outright, and the one she keeps is something she is quietly proud of. If she says the geography round would sink you both, she is probably right.
What if we could repeat one day we have had together, start to finish? Which day would you choose?
Why ask it
The day she picks is seldom the expensive one. Find out what made it, the weather, the lack of a plan, the talk on the way home, because that is the part you can have again.
What if we had met five years earlier? Do you think it would have worked?
Why ask it
An invitation to be honest about who each of you was back then. Whether she says yes or no, her reasons are a description of how she thinks she has changed since.
What if I had one whole day to plan for you, with no budget? What should be in it?
Why ask it
These are instructions, so take notes. Listen to the pace as much as the places: some people want a full itinerary and others want one good thing and a long lunch.
If you had to describe me to a stranger in three sentences, what would you say?
Why ask it
You learn which of your traits she leads with, and it is rarely the one you would have chosen. Describe her in three sentences afterwards so that it is a trade.
What if you could read my mind for one hour? When would you use it?
Why ask it
The hour she picks is the one where she finds you hardest to read: after an argument, on a quiet drive, the time you said nothing was wrong. Tell her what she would have heard.
If I were having a terrible week and not saying so, how would you know?
Why ask it
Her answer is a list of your tells, and one or two of them will be news to you. Return the favour by describing hers, and ask what she wants from you when you spot them.
What if we could have one of our arguments over again? Which one, and what would you do differently?
Why ask it
Keep this for a calm evening and go second. When your turn comes, name what you would change in yourself and leave out what you wish she had done.
If the two of us had a rule book with only three rules in it, what would you write?
Why ask it
Rules people volunteer tend to come from something that went wrong once: phones at dinner, going to bed angry, making plans for two without checking. Agree on her three and add one of yours.
Our future
What if we were both given the same month off? Where would we be by the second week?
Why ask it
By the second week a holiday has turned into a way of living, so she is really describing a pace. Somewhere new every few days and one town long enough to have a usual cafe are different answers.
What if we got a pet together? What would it be, and who would end up doing the early walk?
Why ask it
The animal is the fun half and the early walk is the real half. How she shares out the chores in a made-up case is a fair preview of how she expects them shared in a true one.
What if we shared a home one day? What would you insist on, and what would you happily leave to me?
Why ask it
Meant for a couple who do not live together yet; if you already do, ask what she would change. The things she insists on will be small and exact, a window that opens, a table big enough for friends.
What if we came into some money that had to be spent together within a year? What would we do with it?
Why ask it
A trip, a deposit, a car, giving part of it away: the split she proposes shows how she weighs fun against security. Keep it a game, since nobody is signing anything tonight.
What if one of us were offered a dream job in another city? How would we decide?
Why ask it
Far easier to talk through as a what-if than on the day an offer lands. Aim for the method, who gets a say, how long you would give it, what would bring you back, and do not ask for a promise.
What if we wanted different things one day, such as where to live or whether to have children? How would you want us to handle it?
Why ask it
Nobody has to state a position. The question is how she wants a big disagreement handled: straight away or slowly, between the two of you or with someone else's help.
What if we could visit ourselves ten years from now for one evening? What would you hope to walk in on?
Why ask it
An evening, and not a wedding or a house, keeps her answer to the texture of a life: who is cooking, how loud it is, whether a dog or a child is underfoot. Describe your own version too.
If you wrote me a note to open a year from today, what would it say?
Why ask it
A year is close enough that she has to write something she can be held to: a hope, a bet, a promise. If the idea appeals to her, write the notes for real and agree on the drawer they will live in.
What if we could keep only one thing about us exactly as it is now? What would you protect?
Why ask it
Whatever she names, the slow Sunday mornings, the running jokes, the way you make up after a row, is what she would miss first once life gets busy. Guard that thing on purpose.
Getting Real Answers Out of a What-If
Practical guidance for the conversation itself
Which group suits where you are
A girl you have just started seeing
Stay in Light. Nothing there assumes a relationship, and a what-if about a plane ticket or a talent show gives her room to be funny without being interviewed. The first four in Her life are safe too. Leave the questions that begin 'what if we' alone for now: asked in week two they sound like a plan she never agreed to.
A girlfriend of a few months
Her life and Looking back are where the conversation gets good, because you know enough about her to ask a second question and not so much that you can guess the first answer. Each group gets heavier as it goes, so start at the top of one and stop when the answers slow down.
A couple who have been together a long time
The two of us and Our future were written for you, but do not skip Light. You have never asked her most of those, and the ones you have asked are worth asking again, since what she would do with a year abroad at twenty-two and at thirty are different trips.
One what-if, not a quiz
A single good what if question over dinner beats ten read off a phone. Choose one from the group that fits, answer it yourself as well, and let her ask you one back. If she takes the phone and starts picking her own, it is working.
How to ask them
- Stop at three or four in an evening, even when it is going well. The ones you did not get to are the reason to do it again next week.
- Give your own answer first on anything personal. It sets the depth and takes the pressure off her going first.
- Side by side beats face to face. A drive, a walk or cooking together gives her somewhere to look while she thinks.
- Ask the light ones over text if you like, but save anything about worry, family or the hardest year for in person.
- Let her revise. Many people give a modest first answer and a truer one a few minutes later if nobody fills the gap.
Follow-ups worth having ready
- 'What made you think of that?' moves her from inventing an answer to remembering something.
- 'Did you ever nearly do it?' turns a hypothetical into an actual event you had not heard about.
- 'What would you have said five years ago?' shows how the answer has moved.
- 'Is that something you want, or something you think you should want?' is worth asking gently on the skill and career answers.
- Say her last few words back as a question. It asks for more without steering.
What ruins it
Reading the light answers as evidence
A superpower or a talent-show act is not information about the relationship. Treating it as though it were teaches her to give safe answers.
Turning an answer into a project
If she says what she would do with unlimited time and you respond with a plan, the honesty stops. Sit with the answer first.
Bringing it up later in an argument
Anything she says about regret, worry or family is not material for a disagreement three weeks from now. Using it once ends the whole category of conversation.
Skipping to the hard ones
The hardest year, the thing she has always wanted to hear from her family and the what-if about wanting different things work after twenty minutes of easy talk and land badly as an opening move.