Questions to Ask Your Girlfriend
Questions for the woman you're dating, whether it has been three months or three years. They move from Light through Getting closer, Us and Future to Hard, and each one has a note on what her answer is likely to show you and where to take it next. Answer every question you ask: that's the deal.
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The questions
Each question, and why to ask it
Light
What's the most overrated supposedly lovely thing: brunch, beach days, surprise parties, something else?
Why ask it
Permission to dislike something everyone is meant to enjoy. File the answer carefully, because it doubles as a list of things never to plan for her.
What's on your personal list of foods that are not worth the effort of eating?
Why ask it
Pomegranates, crab legs, anything with a shell. A harmless argument waiting to happen, and useful knowledge when you're the one cooking.
What did you collect as a kid, and where is the collection now?
Why ask it
Where it ended up is the better half. Whether it sits in a labeled box or vanished long ago says something about how she treats her own past.
What was the most elaborate make-believe game you ran as a kid?
Why ask it
Notice her role in it: director, star, or the one who drew the maps. Childhood games are a decent forecast of how she likes to run a project.
What word or phrase do you use so much that your friends tease you about it?
Why ask it
If she can't think of one, you probably can, which tests how closely you've been listening. Go easy: people are attached to their phrases.
Which fictional character did you have a crush on, and what do you think that says about you?
Why ask it
Asking her to do the analysis is the trick. She'll be funnier and more honest about her own taste than you would dare to be.
What's the worst gift you've ever had to pretend to love?
Why ask it
Comedy with a practical payoff. Pay attention to why it was bad: too generic, too practical, or proof that someone hadn't been listening.
What small luxury would you keep even if money got tight?
Why ask it
Whatever she'd defend, good coffee, fresh flowers, nice sheets, is what makes her feel like a person. Also the easiest gift idea you'll ever be handed.
What rule in your childhood home did you later find out wasn't normal?
Why ask it
Every family has an odd law: no shoes on the stairs, no singing at the table. It's a funny side door into how her household ran.
Which season are you, as a person, and which one do you think I am?
Why ask it
Silly on the surface, but people pick with care and then explain themselves at length. Her verdict on you is the part to listen to.
If you could be instantly world-class at one thing with no practical use, what would it be?
Why ask it
Removing usefulness removes the sensible answer. What's left is pure appetite, juggling, yodeling, competitive sandcastles, and that's the fun of it.
When have you laughed at exactly the wrong moment?
Why ask it
Assemblies, ceremonies and serious meetings feature heavily. The story is nearly always good, and you find out who she can't make eye contact with.
What's a fear of yours that you know perfectly well is ridiculous?
Why ask it
Moths, escalators, the phone ringing. Conceding that a fear is silly makes it easy to share, and you learn what to quietly deal with for her.
Which school subject did you love and have had no use for since?
Why ask it
There's often a small sadness in it: the ancient history or the pottery she was good at and dropped. Ask what she liked about how it made her think.
What was the best day you've had that cost almost nothing?
Why ask it
A guide to what she enjoys once spending is off the table. Steal the structure of that day for a date, without announcing that you've done so.
What's the text from me you'd be most likely to screenshot and send to a friend?
Why ask it
She has a group chat and you have appeared in it. Asking with a grin shows you know, and tells you which version of you gets passed around.
Getting closer
What did you spend hours doing as a kid without anyone making you?
Why ask it
Unforced childhood hours point at what absorbs her by nature. Ask whether anything in her life now gives her the same lost-track-of-time feeling.
Which place has felt most like home to you, and what made it that?
Why ask it
It may not be where she grew up. The ingredients she lists, light, noise, people dropping by, are worth remembering if you ever share a front door.
Which friend of yours knows a version of you that I haven't met yet?
Why ask it
Old friends hold earlier editions of a person. Ask what that version was like, and take it as a hint about who you should get to know better.
What do people tend to assume about you when they first meet you, and how wrong is it?
Why ask it
She has had years to be irritated by this, so expect a quick answer. It also invites the question of what you assumed, so have that ready.
Who outside your family had the biggest hand in how you turned out?
Why ask it
A teacher, a friend's mother, a first boss. People love being asked about whoever took an interest in them, and it explains a lot about her standards.
What's the best advice you ever ignored?
Why ask it
There's self-mockery built in, which keeps it from getting heavy. Whose advice it was matters too: it tells you who she wishes she'd listened to.
What unwritten rule do you live by that you've never told anyone?
Why ask it
Most of us have a few: never arrive empty-handed, never be the last to leave. Hearing hers explains behavior you may have noticed and not understood.
What's a kind of attention you enjoy, and a kind that makes you want to leave the room?
Why ask it
Some people love a speech in their honor and others would rather hide under the table. Knowing which she is prevents at least one well-meant disaster.
What do you do to look after yourself that really works, and what only pretends to?
Why ask it
The pretend one is usually scrolling. Knowing the real one, a run, a bath, a call with her sister, means you can nudge her toward it on a rough day.
What memory do you go back to when you need comfort?
Why ask it
A kitchen, a car ride, one particular summer. You're being shown where her sense of safety comes from, so treat the details as something to keep.
What's the hardest thing you've ever talked yourself into doing?
Why ask it
It comes with a built-in story of doubt, a decision and an outcome. You also learn the voice she uses on herself when she needs courage.
What were you praised for most as a child, and did it ever start to feel like a job?
Why ask it
The clever one, the helpful one, the easy one. Praise can harden into a role, and she may still be working shifts in it.
Who in your family are you most like, and how do you feel about that?
Why ask it
Expect a fast answer to the first half and a slow one to the second. The pause is where her real relationship with that person lives.
What did you believe about yourself at sixteen that turned out to be wrong?
Why ask it
Usually something harsh: not clever, not likeable, not the pretty one. How she found out it was wrong is a story about who was good to her.
What are you tired of being the reliable one for?
Why ask it
Capable people get handed things until they sag. If she names something, the kind move is not sympathy but quietly taking one item off the pile.
What are you still figuring out how to say no to?
Why ask it
Extra work, a demanding friend, family errands. It shows you where her edges are soft, and warns you not to become one more thing she can't refuse.
What's something about the way you grew up that you only understood once you'd left?
Why ask it
Distance turns normal into noticeable. Whether it's money, faith, noise or silence, she's telling you what she had to translate for herself as an adult.
What do you envy in other people, even though you'd rather not?
Why ask it
Envy is a rude but accurate compass. What she envies, ease, confidence, a settled home, points at something she wants and hasn't said.
Us
When you tell people how we met, what do you leave in and what do you leave out?
Why ask it
Everyone edits their origin story. Her cut tells you what she finds romantic about it and what she'd rather her aunt never heard.
What's been our best day so far?
Why ask it
Short, and harder than it looks. Compare answers: if you each pick a different day, you now have two templates for a good one.
Which of our inside jokes would be hardest to explain to an outsider?
Why ask it
Trying to explain it is the entertainment. A couple's private language is a real sign of closeness, and it's pleasant to take inventory.
Which photo of us do you think shows what we're really like?
Why ask it
Rarely the posed one. The picture she chooses, mid-laugh, badly lit, slightly chaotic, is her idea of the two of you at your most accurate.
What does a perfect lazy Sunday with me look like, and how is it different from a perfect one alone?
Why ask it
The gap between the two is not an insult. It tells you what she gets from solitude, and lets you give it to her without feeling shut out.
What's something I said offhand that you've held onto?
Why ask it
You will not remember saying it, which is the point. Words land harder than the speaker knows, and this shows you which kind land with her.
What do you think our friends say about us as a couple once we've left the room?
Why ask it
An outside view, borrowed. Her guess reveals what she thinks the two of you project, and whether she believes the projection matches the truth.
What do you think I'm like when you're not around?
Why ask it
Her guess shows how well she thinks she knows you, and whether she imagines you messier, sadder or more fun. Correct the record kindly.
What did we do in the early days that you miss?
Why ask it
Long calls, handwritten notes, dressing up for no reason. Early habits fade because they take effort, and bringing one back is an easy win.
What part of your typical week do I know the least about?
Why ask it
Look for the invisible load: a draining commute, a difficult colleague, a relative who calls daily. It changes what you ask of her on a Thursday.
When you're having a rough time, do you want me to fix it, listen, or distract you?
Why ask it
Asking in advance spares you from guessing wrong in the moment. The answer can change by the day, so it's fair to ask again when it's happening.
How do you like to be apologized to?
Why ask it
Some want the words, some want changed behavior, some want a day and then a hug. If you've been apologizing in your own style, this explains a lot.
What makes you feel chosen?
Why ask it
Different from feeling loved. Chosen is about priority: being introduced, being planned around, being picked over an easier option. Ask for an example.
What's something you've learned about yourself from being with me?
Why ask it
Good relationships teach people things, flattering and not. She might say she's more patient than she knew, or less. Both are useful.
Which of my friends or family are you most at ease with, and who is still hard work?
Why ask it
She has opinions and has been polite about them. Don't defend the hard-work person. Ask what would make those occasions easier for her.
What role do you end up playing between us, planner, peacemaker, rememberer of birthdays, and do you want it?
Why ask it
Roles settle in without a vote. If she's tired of hers, this is the vote, and the fix is usually you taking something over without being reminded.
What did you almost not like about me at the start?
Why ask it
Risky, with a good payoff: you hear the thing she got past, and she gets to tell you how. Only ask if you can take it as a compliment.
When do I seem most distracted, and how does that land with you?
Why ask it
You're asking for criticism in a form that's easy to give. Expect the word phone. Don't explain: ask what she'd like you to do differently.
What's one thing you'd like us to get better at?
Why ask it
The word us matters: it's a joint project, not a complaint about you. Pick one thing only, and agree on a small next step, not a grand reform.
When we disagree, what do I do that makes it harder to talk to me?
Why ask it
Going quiet, getting loud, reaching for a list of past offenses. She knows your move. Hearing it named in peacetime makes it easier to catch.
Future
What trip do you want us to take before life gets more complicated?
Why ask it
The destination matters less than the phrase 'more complicated', which invites her to say what she thinks is coming. Then start pricing the trip.
If you were handed a paid year off, what would you do with the first month and with the last?
Why ask it
Month one is rest, and the final month is who she wants to be. Splitting it stops the answer from being nothing but sleep and a beach.
What do you need within walking distance to be happy living somewhere?
Why ask it
A bakery, a park, her best friend, nothing at all. It turns the vague question of where to live into a checklist the two of you can compare.
What tradition would you like to start that neither of our families has?
Why ask it
Inherited rituals come with baggage, and invented ones are entirely yours. Even a silly one, pancakes on the first cold day, gives you something to build.
How do you want the big birthdays and milestones marked: a crowd, a trip, or a quiet dinner?
Why ask it
Ask well before one arrives. People feel strongly, rarely say so, and then sit through a party they didn't want, smiling at you.
What do you want your friendships to look like ten years from now?
Why ask it
Partners often forget to ask about this. If she wants friends dropping by on weeknights and you want a quiet house, better to find out early.
If you could redesign your working life from scratch, what's the first thing you'd change?
Why ask it
Whatever she changes first is the sore spot: the hours, the boss, the whole field. Whether it's small or total tells you how settled she feels.
What does success look like for you that has nothing to do with work?
Why ask it
Behind an impressive job there's often a quieter ambition: a garden, a long table of friends, being a good aunt. That's the one to back.
What do you want to have made, built or finished by the time you're old?
Why ask it
Not everyone has an answer, and that's fine. If she does, it's something you'll be living alongside, so ask what it needs from the next few years.
What are you saving for, literally or otherwise?
Why ask it
Literally gets you a goal. Otherwise gets you the thing she's holding energy back for, which can be more revealing than the bank answer.
What do you think we'll laugh about in ten years that feels serious now?
Why ask it
It shrinks a current worry by looking at it from a distance, and tells you which one is on her mind. A kind thing to ask in the middle of a stressful month.
What would you look forward to about living together, and what would worry you?
Why ask it
If you already share keys, ask it about the next home instead. The worries are usually about space and chores, which makes them fixable.
What would you want to keep as just yours, even in a fully shared life?
Why ask it
A room, an account, a hobby, a friendship. Wanting something separate isn't distance. It's often what makes the shared part sustainable.
When life gets busier, how should the work of running a home be split: by skill, by schedule or by turns?
Why ask it
Naming three systems makes it a design question instead of a grievance. Ask what she saw growing up, since that's the default she's arguing with.
When one of us hits a brutal stretch at work, what should the other reasonably expect?
Why ask it
Crunch periods strain couples because nobody set terms. Agreeing on a minimum, one proper evening a week, a daily call, keeps resentment from filling the gap.
Which purchases should a couple always discuss first, and below what size is it nobody's business?
Why ask it
A practical way into money that doesn't ask what she earns. The threshold she names tells you how much financial privacy she expects to keep.
What's your biggest fear about money?
Why ask it
Running out, owing someone, depending on a partner, never feeling safe. The fear usually has a history, and knowing it explains her spending and her saving.
If a proposal ever happens, how should it go: private or public, a surprise or talked through first?
Why ask it
Hypothetical on purpose, so nobody panics. Guessing wrong about this is a classic and avoidable mistake, and she almost certainly has views.
If we raised a child, what would you want them to say about their childhood when they're thirty?
Why ask it
It sidesteps the yes-or-no and goes to values. If she isn't sure about children at all, she'll say so here, and that's worth hearing plainly.
What would you never want to give up for a relationship or a family, however yours turns out?
Why ask it
Her work, her city, her Saturday mornings, her name. It's easier to honor a line when it's been drawn before anyone is standing on it.
Hard
What do you think I expect from you that I've never actually asked for?
Why ask it
She may be meeting standards you never set: always cheerful, always available, always fine. Hearing the list lets you cancel the ones you never wanted.
What's the argument we keep having in different costumes?
Why ask it
Plenty of couples have one underlying fight that turns up as dishes, lateness or tone. If you can both name it, you can argue about the real thing for once.
How do you feel about the way I talk about you in front of other people?
Why ask it
Teasing that feels affectionate to you can feel like exposure to her. She has probably never raised it, because it sounds petty until someone asks.
Is there a boundary with my family or friends that you'd like me to hold for you?
Why ask it
She can't easily police your people, and she knows it. If she names something, holding that line is your job, and doing it without fuss earns a lot of trust.
When have I made you feel small, even if I didn't mean to?
Why ask it
The closing clause gives her room to say it without calling you cruel. Don't argue with the memory. Your intent isn't the subject, the effect is.
What part of yourself do you turn down around me?
Why ask it
Her ambition, her silliness, her temper, her faith. People dim whatever they suspect isn't welcome, and she may be wrong about what you can handle.
Is there an insecurity of yours that gets louder around me instead of quieter?
Why ask it
Uncomfortable, because the answer may involve you. If something you do feeds it, a comment, a comparison, you'd want to know. Listen without defending.
What do you still brace for with me because of how someone treated you before?
Why ask it
Old injuries set off alarms in new relationships. Knowing what she's braced for lets you stop tripping it by accident, and explains reactions that seemed outsized.
When have you felt like you were carrying more of this relationship than I was?
Why ask it
There has almost certainly been a time. Ask what carrying looked like, the planning, the emotional upkeep, the reaching out, so you can spot it next time.
When you picture telling me bad news, what reaction of mine do you expect?
Why ask it
Her prediction is a report on how safe you are to confide in. If she expects panic, blame or a lecture, the thing to work on is you, not her forecast.
Do you feel you can be properly angry with me without it costing you something?
Why ask it
If she manages her anger in order to manage your reaction, you have a problem that looks like peace. A slow or careful answer is an answer.
What have you forgiven me for that still stings now and then?
Why ask it
Forgiven is not the same as gone. Letting her say it still aches, without reopening the trial, is often what finally lets it fade.
What do you think I still don't understand about what it's like to be you?
Why ask it
Broad on purpose: it could be her job, her family, or moving through the world as she does. Believe the answer even if it doesn't match your view.
How have you changed since we got together, and is there any of it you're not sure you like?
Why ask it
Relationships reshape people, not always toward who they wanted to be. If she has lost a habit, a friend or some nerve, help her get it back.
If I changed in a big way, new career, new beliefs, a new city in mind, what could you bend on and what couldn't you?
Why ask it
We all change, and promising otherwise is how couples get blindsided. Knowing which parts of the deal are fixed for her is a kindness to both of you.
What scares you about committing for the long haul, even to someone you're sure of?
Why ask it
Being sure of a person and being afraid of forever can coexist. Hearing the fear, boredom, losing herself, being left, is not hearing a no.
If one of us developed a crush on someone else, would you want to be told?
Why ask it
It happens in long relationships, and couples differ sharply on the etiquette. Agreeing on the rule in the abstract is far easier than mid-crisis.
What hope do you have for us that feels risky to say out loud?
Why ask it
Hopes are scarier to admit than complaints, because they can be turned down. Whatever she says, don't negotiate it on the spot. Just hold it.
Is there anything about your health, body or mind, that you've been managing quietly on your own?
Why ask it
Bring no agenda and plenty of time. Many people handle things privately out of habit, and the offer of company can matter more than any advice.
If you hit a really dark stretch and started pushing me away, what would you want me to do?
Why ask it
Raise it while things are good, because she can't tell you when she's in it. You're collecting instructions from the well version of her for the unwell one.
Is there a grief you carry that I should understand better?
Why ask it
A person, a place, a version of her life that didn't happen. You don't need to fix it. Learn the dates that matter and the name to say.
Asking well, and what to do with the answers
Practical guidance for the conversation itself
Before you ask anything
Go first
Answer the question yourself before you ask her, out loud, at the depth you're hoping for. It shows you're not running an assessment, and it sets the level. If you wouldn't answer a question, you haven't earned the right to ask it.
Check your motive
Curiosity is a good reason to ask. Fishing for reassurance, building a case or testing her against a checklist are bad ones, and she'll sense the difference within a sentence. If a question has a correct answer in your head, leave it on the list.
Agree that either of you can pass
Say at the start that a question can be skipped with no explanation and no sulking. The freedom to pass is what makes honest answers possible on the ones she takes. A skipped question is not a clue to be decoded later.
Put the phone somewhere else
Reading questions off a screen is fine. Glancing at notifications between them is not. Silence the phone first, or copy a few questions onto paper and leave the phone in another room.
Formats that work
Slips on the table
- 1Each of you picks three questions from the list and writes them on slips of paper.
- 2Shuffle the slips face down. Take turns drawing one, and whoever draws it answers first.
- 3The other person answers the same question before the next slip is drawn.
- 4Leave any undrawn slips for next time. There's no prize for clearing the table.
The long-distance version
- 1Send one question in the morning as a voice note, along with your own answer.
- 2She replies whenever she likes, by voice, not text. Tone carries half the meaning.
- 3Keep the Hard section for a call or a visit. Heavy answers deserve a live listener.
- 4Save the good ones. A folder of voice notes ages better than a chat log.
The yearly review
- 1Around an anniversary, pick a few questions from Us and Future that you've both answered before.
- 2Answer them again without looking up what you said last time.
- 3Compare. Notice what moved and what held.
- 4Choose one thing from the conversation to act on before the next review.
Listening, and afterwards
Follow up before you reply
The best second question is usually 'what was that like?' or 'say more about that'. Ask at least one follow-up before you offer your own story. It's the difference between a conversation and two people taking turns to talk.
Don't fix what she tells you
If an answer reveals a problem, the urge to solve it on the spot is strong and usually unwelcome. Ask whether she wants ideas or wanted it heard. Most of the time it's the second, and she'll tell you when it's the first.
Never use an answer as ammunition
Whatever she tells you in one of these conversations stays out of future arguments. The first time a confidence comes back as a weapon is the last time she gives you one. The same goes for repeating her answers to your friends.
When an answer hurts
Say 'thank you for telling me', and mean it, before anything else. You're allowed to be stung, and you can say so, but don't ask her to take it back or soften it. Return to it in a day or two, when you can be curious instead of defensive.
Act on one thing
A good conversation that changes nothing becomes, over time, a reason not to have another. If she told you she misses something or needs something, do it within the week without announcing it. That's what makes the next question worth answering.