Questions to Ask My Daughter's Boyfriend
For a parent working out what to ask a guy dating your daughter without the evening turning into an interrogation. These 65 questions start with ten built to run in both directions: he answers, you answer the same thing back, and a couple of them hand him the floor to ask about your household. The aim is that he leaves feeling welcome and slightly better briefed on how this family works. The second group is for the first few times you meet your daughter's new boyfriend, when a nervous guest needs things he cannot get wrong: what to call him, where he grew up, what he has stuck with. Another is for the teenage version, often her first boyfriend, when a boy is asking to date her or is standing in the hall as your daughter's date for the night: where they are going, who else will be there and how she gets home. The later questions are for when you know him better: whether he has met her friends, what he does with anger, how he takes being told no, and, once he is part of the family calendar, money, plans and where you fit.
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The questions
Each question, and why to ask it
Goes both ways
What were you nervous about before you came over?
Why ask it
It names the awkwardness instead of pretending it is not there, and almost everyone has an answer. Saying it out loud tends to drop the temperature at the table by half.
What have you heard about this family that you are not sure is true?
Why ask it
He has been briefed by your daughter, and this lets him check the briefing with you rather than tiptoe around it. You also find out what she says about you when you are not in the room.
What is a rule in your house that we would not have here?
Why ask it
Households run on unwritten habits about shoes, doors, food and volume, and he is quietly guessing at yours. Comparing them is easy to talk about and saves him getting one wrong later.
Who did the cooking in the house you grew up in?
Why ask it
A gentler way into family than asking him to describe his parents, and it gives him a concrete scene to answer with. What he treats as ordinary is the part worth noticing.
Is there anything you want to ask us, about her or about this family?
Why ask it
Handing him the floor turns an inspection into a conversation. Whatever he asks tells you what he has been worrying about, and often it is simply whether you like him.
What would make it easier to come over here next time?
Why ask it
His answer is likely to be practical and small: being told what time dinner actually is, where to park, whether he is meant to knock. Small is good, because you can have it fixed by his next visit.
Who in your life will tell you the truth when you do not want to hear it?
Why ask it
Everyone needs one person allowed to say the unwelcome thing, and it is worth knowing whether he has one. Tell him who yours is. If he cannot name anybody, treat that as information rather than a verdict.
What is the hardest thing you have had to sort out on your own?
Why ask it
This is the character question, and it works because it asks for competence rather than virtue. Listen for whether he asked anyone for help in the end, and have your own answer ready, because he may well ask.
What do you think we have got wrong about you so far?
Why ask it
First impressions are wrong in some specific way and he usually knows which way. Asking for the correction is the clearest signal that you are not compiling a file on him.
What would you want us to know about you that does not usually come up?
Why ask it
The choice of subject is entirely his. Some will mention a family situation or a hard year, and how you receive that answer sets the tone for the next several years.
New boyfriend
Have you eaten, and is there anything you don't eat?
Why ask it
The first thing you say should give him something to do and somewhere to stand. It also quietly establishes that he is a guest rather than a suspect, which is the whole tone of a first visit.
What should we call you?
Why ask it
Plenty of young men go by a middle name or a nickname their own family never uses, and your daughter may have introduced him by the formal one. Settle it early and tell him what to call you, which he has been wondering since the car.
How did you two meet?
Why ask it
An easy start, and worth hearing in his words rather than hers. Notice whether other people appear in the story, and whether he gives her any credit for how it began.
How long have you two been seeing each other?
Why ask it
Ask him even if she has already told you, since each of them may be counting from a different evening. A gap of a month or two is no scandal. It only means they have not yet agreed on when this began.
Where did you grow up?
Why ask it
There is no wrong answer to this one, which is its use with a nervous guest. A town's name tends to drag a school, a move or a parent's job along behind it, and you learn how far from home he is now.
Who's in your family, and are you close with them?
Why ask it
How he talks about the people who raised him previews how he will talk about you in a few years. Warmth is good, honest distance is fine, and flat contempt for all of them is the answer to sit with.
What are you working on right now, at school or at a job?
Why ask it
Asking what he is doing rather than what he plans to become keeps a young man off the witness stand. A specific answer about an ordinary job tells you more than a polished five-year plan.
What have you been into lately, a game, a show, a sport?
Why ask it
A shy young man can talk for five minutes about a game or a team, and five easy minutes is most of what a first visit is for. Follow up on whatever he names. You are finding out whether he can carry a conversation, not marking his taste.
What do the two of you usually do when you spend time together?
Why ask it
A couple who cook, drive somewhere or see friends have more to go on than a couple who only watch things side by side, though at the start most do a bit of both. Listen also for whether they are ever around anyone else.
What do the two of you end up talking about most?
Why ask it
A shared subject, a band, a class, his sister, her job, gives a couple something to be besides a couple. If he cannot think of one, they may still be at the stage where being in the same room is the whole attraction, which is common in the first months.
Who do you spend time with when you're not with her?
Why ask it
His friends are the world your daughter is stepping into. Named people and ordinary plans are reassuring. If he has no one but her, note it, because a man with no other ties tends to lean his whole weight on a girlfriend.
What's something you're better at than most people would guess?
Why ask it
Gives him one chance to be interesting instead of merely well behaved, which loosens up everything after it. A deflection here is usually nerves rather than emptiness, so leave room to come back to it.
Is there something you've stuck with for a long time?
Why ask it
Six years of trumpet, a team, a Saturday job or looking in on a grandparent says what no stated plan can, that he keeps going once the novelty has worn off. It is also kinder than asking about his ambitions, because the evidence already exists.
What's something you're stubborn about?
Why ask it
People own up to stubbornness far more readily than to faults, so you get a true answer about where he does not bend. A joke about how to load a dishwasher still counts if it is specific, and your daughter's face while he answers is worth a glance.
What's the last thing you saved up for?
Why ask it
A concrete answer, a used car, an amp, a trip, shows he can want something and wait for it. "I don't really save" is not damning at nineteen, but it hints at who ends up paying for their plans.
Before a date
When you say you'd like to date her, what does that look like to you?
Why ask it
At fifteen, dating can mean texting and sitting together at lunch, or it can mean a car and every Saturday night. You cannot say yes to a prospective boyfriend until you know which of those he is asking for.
How old are you, and what year are you in at school?
Why ask it
Basic, and far easier to ask in the first minute than the tenth. A gap that would be nothing between adults can matter a good deal between teenagers, so find it out early, in the tone you would use to ask his name.
Did you ask her out, or did she ask you?
Why ask it
A light one that usually gets a grin and a slightly different story from the one she told. If she did the asking, admitting it in front of you costs him a little pride, and it is easy to like someone who pays that cheerfully.
What has she told you about our rules for going out?
Why ask it
You find out whether the rules were passed on accurately, and you get to correct them without giving a lecture. If she added an hour to the curfew in the telling, smile and give him the real one.
Where are the two of you headed tonight?
Why ask it
The plainest question a parent can ask her date, and the one that least needs an apology. A boy who can name the place and roughly when it finishes has thought about the evening beyond picking her up.
Who else is going to be there?
Why ask it
Just the two of them, a group of friends, and a house with or without adults in it are very different evenings. Asked as interest in his friends, it comes across as exactly that.
Is anyone likely to be drinking where you're going?
Why ask it
Put plainly, it tends to get a plain answer, and "probably, some of the older ones" is more use to you than a promise that nobody will. Follow it with the deal that matters: either of them can ring you for a lift at any hour, and neither gets into a car with a driver who has been drinking.
How are the two of you getting there and back?
Why ask it
The ride home is the part of a date most likely to change at the last minute. Once you have heard his plan, say that a lift from you is always available, with the questions kept until morning.
Do you drive, and what are the rules at your house about that?
Why ask it
A practical safety question that sounds like ordinary curiosity. Many places limit the passengers a newly licensed driver can carry or the hours he can be on the road, so ask what his licence allows where you live.
What time do you need to be home?
Why ask it
His curfew settles the evening's logistics and tells you whether his household has expectations at all. If hers is the earlier of the two, hers is the one the evening runs to, and this is the moment to say so.
If plans change tonight, how will I hear about it?
Why ask it
Agree the mechanism, a text from either of them, before it matters. Asking him directly rather than only your daughter makes him part of the arrangement instead of the reason for it.
Can we swap numbers before you go?
Why ask it
Phones run flat and get left in coat pockets, so hers alone is one point of failure. Adults arranging anything exchange numbers as a matter of course, and putting it that way stops it sounding like surveillance.
Do your parents know where you'll be tonight?
Why ask it
It puts both households on the same footing, since you are asking for no more than his own family would. If the answer is no, better to hear it while the car is still in the drive.
What would you do if she wanted to go home early?
Why ask it
The answer to listen for is three words long: take her home. Any talk of persuading her to stay a while deserves a calm follow-up about whose decision that is.
If the evening turned into something neither of you had planned on, what would you do?
Why ask it
Parties move, friends turn up with other ideas, and a film becomes somebody's empty house. Letting him say out loud that he would leave makes leaving easier when the moment comes.
How he treats her
What's she like when I'm not around?
Why ask it
Asked lightly, this gets a genuinely useful answer, because he sees a version of her you do not. Affectionate detail is a good sign; anything mocking, even as a joke, is worth filing away.
What do you like about her that she would be surprised to hear?
Why ask it
Better than asking what he likes about her, because the surprise forces something observed rather than complimentary. A vague answer from someone months into a relationship is one to remember, though not to remark on.
What does she do that makes your life easier?
Why ask it
It checks whether he notices being looked after. If nothing comes to mind, the lifts, the reminders and the saved seat may never have registered with him, and better to learn that now than after she has kept it up for years.
What is something the two of you do completely differently?
Why ask it
Lighter than asking about arguments, and closer to what couples actually live with, which is differences in habit. He gets to be fond of her without having to perform it.
What's something she has changed your mind about?
Why ask it
A boyfriend who can name a change she caused is a boyfriend who listens. Coming up blank often means he treats the relationship as something happening to him rather than something he takes part in.
Have you met her friends yet, and which of them do you get on with?
Why ask it
Her friends knew her before he did, and the way he speaks of them shows whether he is joining her life or drawing her out of it. One or two liked by name is the good answer. If he finds every one of them annoying, say nothing and keep watching.
How much are the two of you in touch during the day?
Why ask it
With teenagers this is partly a phone question, and a house rule about screens at night applies to her whoever is texting. At any age, listen for whether a slow reply is ordinary between them or something she has to explain.
When the two of you disagree, how does that usually go?
Why ask it
You are asking about mechanics, not verdicts: who leaves the room, how long the silence lasts, who speaks first afterwards. "We never argue" after several months can mean one of them is swallowing things.
What do you do with yourself when you're angry?
Why ask it
The habit matters more than the feeling. Going for a drive, going quiet for three days, punching a wall and having a few drinks are four different answers with four different consequences for your daughter.
What's the last thing you had to apologize for?
Why ask it
Being wrong is ordinary, describing it plainly is not. Watch whether the story holds its shape or drifts, by the end, into everyone else's fault.
What do your friends do when one of them is out of line?
Why ask it
A sideways route to his standards, since it is easier to describe what a group puts up with than what you put up with yourself. A group where nobody ever says anything is its own answer.
Growing up, how did people in your house handle it when they were upset with each other?
Why ask it
Plenty of people either repeat the way the house they grew up in argued or work deliberately against it. Both answers are useful, and a young man who knows which one he is doing has already done some thinking.
What happens when she says she wants a night to herself?
Why ask it
A request for space is often the first place control shows. The thing to hear is whether her night off is unremarkable or something she has to negotiate for.
When she's struggling, what do you actually do?
Why ask it
Ask for behaviour, not sentiment. Specific answers, he cancels things, he cooks, he leaves her alone because that is what she wants, mean he has learned her. Generalities about being supportive mean he has not.
Long term
What are you hoping the next couple of years look like for you?
Why ask it
Near-term plans can be checked against reality in a way that lifetime ambitions cannot. Notice too whether she appears in the answer, and whether she is a decision they made or an assumption he is carrying.
If her plans took her a long way from here, what would you do?
Why ask it
Tests whether he thinks of her future as hers. Promises about visiting are easy to make. Listen instead for an answer that quietly assumes she would stay, or that treats her leaving as a betrayal.
What are the two of you planning that we do not know about yet?
Why ask it
Said with a smile, this catches the trips, moves and shared leases parents tend to find out about last. Ask him with your daughter present so it is not a back channel.
How do the two of you handle money, in the boring practical sense?
Why ask it
Not an audit of his income, but of the arrangement: separate, joint, who pays for what, whether they have ever discussed it. Couples who have never had the conversation usually say so by hesitating.
Where do you both want to be living in five years, and do you agree on it?
Why ask it
Geography quietly decides careers, children, and how often you see them. Couples frequently discover they disagree about this while answering it out loud for the first time.
Have the two of you talked about children, and are you in the same place?
Why ask it
Fair to ask once a relationship is settled, provided you accept a short answer and do not press. What matters is whether the conversation has happened at all, not what they concluded.
What do your parents make of her?
Why ask it
You learn how she is treated in the other household, which she may have been playing down. Any hesitation here is worth returning to privately with your daughter, not with him.
How do you want to handle holidays and birthdays between the two families?
Why ask it
This is the practical negotiation that causes years of low-grade friction if it is never made explicit. Raised as planning, it is a short conversation. Raised after one family has already felt passed over, it is a grievance.
What would you want from us if the two of you are still together in a few years?
Why ask it
It gives him a say in the arrangement instead of leaving him to guess at it. Most people ask for something small, such as hearing about plans earlier, and small requests are easy to grant.
How would you want us to tell you if something bothered us?
Why ask it
It sets up a channel before it is needed, which is the only time such an agreement is easy to make. Asking at all tells him you expect to be in each other's lives long enough for it to matter.
Do you want to hear what she was like as a little girl?
Why ask it
Hands him something instead of asking for more, and it usually makes for the warmest part of the conversation. Pick a story she would be pleased for him to hear, and look at her face before the photo albums come out.
Meeting Him Without Interrogating Him
Practical guidance for the conversation itself
Set it up to go well
Talk while doing something
Cooking, driving him home, or washing up after dinner beats a formal chat in the front room. Asked shoulder to shoulder, with something for his hands to do, the same question stops sounding like an assessment.
One parent at a time
Two adults asking questions in turn is an interview panel, whatever your tone. Divide it up and compare notes later.
Tell your daughter first
Say that you want to get to know him and ask what is off limits: a parent who has died, a job he has just lost, a situation at home he would rather not explain. Springing this on her, or on him, guarantees a defensive evening and a conversation with her afterwards.
Give the first visit an end
An hour with a finish built in, dinner and then the two of them are off out, is kinder to a new boyfriend than an open evening. Nobody is left wondering when he is allowed to stand up.
Two or three questions is a whole visit
These work over months, not in one sitting. Anything more than a few in an evening and he will start giving the answers he thinks you want.
A boy dating your daughter gets the short version
At the door before a date, keep it to two minutes: where they are going, who with, home by when, and how you will hear if that changes. State your rules once as the rules of this house, not as a verdict on him, and save the getting-to-know-you questions for a meal.
What meeting her new boyfriend can and cannot tell you
Very little about his character
A first evening with a girlfriend's parents mostly measures nerve. Too quiet, too polite, stiffly formal or a little boastful are all ordinary on a first visit, and most of it has worn off by the third.
A fair amount about his manners
Whether he says hello to everyone, thanks whoever cooked and keeps his phone in his pocket are habits, not nerves, so they show from the first visit. So does whether he checks with your daughter before answering for the two of them.
What actually tells you something
- How he speaks to your daughter when he thinks nobody is paying attention
- Whether he lets her finish her own sentences and her own stories
- How he treats whoever is serving, cleaning up, or youngest in the room
- Whether her plans and friendships have grown or shrunk since they met
- What she is like around him, which is the most reliable evidence available to you
What to leave alone
Money, politics, and religion at a first meeting
None of these can be discussed usefully by two nervous people, and all three are easy to get wrong. If they matter to you, they will come up naturally over a year. Previous girlfriends belong on the same list, since any answer he gives is a guess at the one you want.
His intentions, asked in front of her
Demanding a statement about the future embarrasses both of them and produces whatever answer ends the moment fastest. Ask about the next year instead, and ask them together.
Teasing before you know him
Family humor reads as hostility to someone who cannot yet tell the difference. Save it until he is comfortable enough to give it back.
Real concerns disguised as questions
If you are worried about how he treats her, that is a conversation with your daughter, calmly and without ultimatums. Cross-examining him instead usually pushes her toward defending him.
After he leaves
Tell her one thing you liked
Make it true and specific: that he asked your youngest about her drawings, or carried the plates through without being asked. It costs you nothing, and it keeps her telling you about him, which is where most of what you will ever know comes from.
Keep any worry for another day
Said in the same breath as the compliment, the worry is the only part she will hear. Leave it a day, describe what you saw him do instead of what you think he is, and say it once.
Ask him back before you have made up your mind
The second and third visits show what a first one hides, and the invitation tells your daughter you are not collecting reasons to disapprove.