Questions Not to Ask on a Date
Questions not to ask on a date, for anyone with a first or second one coming up who would like to stop a bad question before it leaves their mouth. These 49 worst questions to ask your date are grouped by subject, beginning with the three big ones, Their past, Money and The future, then the ones that are simply Too personal, the Interview kind and those About tonight itself. Almost none is off limits for good: most are a fair question asked several weeks too early.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Their past
Why are you still single?
Why ask it
It is meant as a compliment and it arrives as a request to explain what is wrong with them. The only ways out are a joke or a confession, and neither is a good start. 'What have the last couple of years been about for you?' covers the same ground and lets dating come into it or stay out.
Why did your last relationship end?
Why ask it
A fair thing to wonder and too much for a first date: the true answer is long, and the short one is a put-down of either the ex or themselves. A few dates in, it becomes a reasonable question. Tonight, should an ex come up, listen to the tone more than the facts and leave it there.
Are you over your ex?
Why ask it
Anyone who says 'completely' sounds defensive and anyone who hesitates sounds unavailable, so you have set a trap without meaning to. Listening will tell you: how often the ex comes up unprompted, and whether it is with heat. A whole evening without a mention is its own answer.
Have you ever cheated on anyone?
Why ask it
Few people answer this truthfully to a stranger, so a 'no' tells you nothing and a 'yes' ends the evening. It also announces that you arrived expecting to be let down. Trust gets measured in small things kept: the time they said, the call they promised, the story that stays the same.
What's your body count?
Why ask it
It asks for a number so you can judge it, and no number pleases everyone: someone will find it too high and someone else too low. It also makes the evening about sex before either of you has decided there will be a second date. Worries about health, or about how seriously they take relationships, are direct conversations for when things are heading that way, and the count answers neither.
How long have you been on the apps?
Why ask it
A long time sounds like nobody chose them and a short time sounds like a rebound, so every answer costs something. 'Has meeting people this way been fun for you, or a bit of a slog?' gets a funnier answer, and trading one bad-date story each is a fine way to spend five minutes.
Have you ever had a relationship that lasted more than a year?
Why ask it
The judgment is in the phrasing: under a year, and they have failed a test they did not know they were taking. Length says little on its own, since plenty of long relationships were bad ones. Their oldest friendship is the better thing to ask about, because it shows whether they stay close to people and nobody is keeping score.
Why did you get divorced?
Why ask it
Mentioning a marriage is telling you a fact, not opening the file. The why involves another person who is not there to give their side. 'That must have been a big change' is enough, and it leaves them to decide how far to go.
Do you want to hear what my ex did?
Why ask it
This one is a question in form only: it is a request for permission to unload. Ten minutes on an ex tells your date that part of you is still in that relationship, and that they might be the next story. Asked about your own past, give it two calm sentences without a villain and hand the conversation back.
Money
How much do you make?
Why ask it
It reads as a price check, and whatever the number is, you will both spend the rest of the evening thinking about it. Whether they like their work and how they live are fair things to be curious about. Ask what a good day at their job looks like; how someone handles money shows over a few dates without a figure.
So, who's paying for this?
Why ask it
Raised before anyone has ordered, it turns the meal into a negotiation and hangs over every line of the menu. Customs differ from place to place and couple to couple, so there is no rule to cite. If you did the inviting, come ready to cover it; when the check lands, 'shall we split this?' or 'let me get this one' is an offer, not a quiz.
Do you own your place or rent?
Why ask it
It sounds like small talk and works as a net-worth estimate, which the other person can hear. In plenty of cities renting says nothing about how someone is doing anyway. Curiosity about their home is better spent on what they like about the neighborhood or how long they have been there.
Do you still live with your parents?
Why ask it
The 'still' has already ruled on it. High rents, family duty and custom make living at home ordinary in a great many places, and you don't know which of those applies. 'What's your setup, roommates or your own place?' asks it without the verdict, and 'with my folks' becomes just one of the answers.
Do you have any debt?
Why ask it
Student loans, cards and a mortgage are things a partner needs to know before sharing a lease, not before sharing a dessert. On a first date it sounds like a background check. It becomes fair when the two of you are talking about combining something, and by then you will be trading numbers, not asking for theirs.
What kind of car do you drive?
Why ask it
Between two people who love cars, this is a fine question. As a quick way to place someone it is obvious, and it embarrasses anyone who came by bus. Car people can say so about themselves first and see whether the other one lights up.
How much did that cost?
Why ask it
Whether it is a watch, a bag, a trip or their rent, the price is the least interesting thing about it, and asking makes you sound like you are adding it up. Ask for the story instead: where they found it, or what made them choose that place to travel. A plain 'that's a great jacket' works too.
Do your parents help you out?
Why ask it
Often asked after hearing about a nice apartment or a long trip, and it says 'you couldn't have paid for that yourself.' Whether there is family money, or a family they are supporting, is theirs to bring up. Stay with the trip itself, where they went and what they would do again, and family will be in the story if it belongs there.
The future
Do you want kids, and how soon?
Why ask it
Whether someone wants children matters, and many people put it on their profile for that reason. The 'how soon' is what turns it into a timetable with them penciled in. When it is a dealbreaker, state your own position lightly as family comes up, 'I'd like kids someday,' and watch whether they lean in or go quiet.
When do you want to be married by?
Why ask it
A deadline makes the person across from you feel like a candidate for an opening. Wanting marriage is nothing to hide: say that you are dating with something lasting in mind and leave the calendar out of it. How they take that one sentence tells you more than a year would have.
Are you looking for something serious, or just wasting my time?
Why ask it
The first half is a fair thing to want to know; the second half accuses them of something they have not done yet. Once the evening has warmed up, say what you are hoping dating turns into and ask whether that is near where they are. Going first is what makes it a conversation and not a screening.
Where is this going?
Why ask it
On a first or second date the only true answer is 'I don't know yet,' and asking makes that sound like a failure. The question belongs to the point where you have been seeing each other regularly. The early version is smaller and easier to say yes to: 'I'd like to do this again. Would you?'
At your age, shouldn't you be settled down by now?
Why ask it
It tells them they are behind on a schedule you made up, and that you have been doing arithmetic on their birthday. Many people have already heard it from relatives and did not come out tonight to hear it again. 'What wouldn't you trade about how things have turned out?' asks about the same life and assumes it went well.
Would you stay home with the kids, or expect me to?
Why ask it
You are dividing the labor in a household that does not exist, with a person whose middle name you do not know. It is a real compatibility question and it deserves a considered answer, which nobody can give on date one. Listen to how they talk about their own work and their own parents; the outline is usually there.
Could you see yourself marrying someone like me?
Why ask it
Said as a joke, it still never quite lands as one: they have to either flatter you or let you down inside the first two hours. There is no early form of this question. The thought is one to share with a friend on the way home, not with a person still deciding about dessert.
Too personal
Who did you vote for?
Why ask it
You ask for one name, and a verdict on the whole person is waiting behind it. 'What's something in the news you can't stop following?' is the more useful version when politics is a dealbreaker: you hear how they think and how they talk about people who disagree, which a name on a ballot does not show.
Do you actually believe all that?
Why ask it
Usually said right after they mention church, prayer, a fast or the faith they grew up in, and the word 'actually' has already answered for you. Real curiosity sounds like 'what part of it matters most to you day to day?' Anyone who needs a partner of the same belief can say so about themselves and see how it is taken.
How tall are you, really?
Why ask it
The 'really' calls them a liar about their profile, and height is one thing nobody can change by Friday. You can already see how tall they are. A height requirement is a filter to apply quietly before agreeing to meet, not something to put to them over dinner.
Why don't you drink?
Why ask it
The reasons run from taste to health to faith to recovery, and none of them is owed to someone they met an hour ago. 'What can I get you?' is the whole question. The story, when there is one, gets told once it feels safe, and how you handled tonight is part of what makes it safe.
Have you ever been in therapy?
Why ask it
Plenty of people would answer happily, and it is still a health question dressed as small talk, put to them by someone they met this evening. How they get through a rough patch shows up when you ask what they do to reset after a bad week. Whether a therapist is part of that answer is theirs to add.
What's the worst thing that has ever happened to you?
Why ask it
Some people ask this to skip the small talk and get somewhere real. It skips the trust too, and the other person has to choose between a painful story and a visible dodge. Start at the other end, with the best thing that has happened to them lately; the hard parts come out later, to someone who has earned them.
Are your parents divorced?
Why ask it
A yes-or-no about what may be the hardest chapter of someone's childhood is a lot for a first coffee, and it can sound like you are checking their odds. 'Who were you closest to growing up?' opens the same door from the kind side. They can answer with a grandmother, a brother or a neighbor and say as much or as little about the rest as they like.
Where are you really from?
Why ask it
When someone has already said where they are from, the 'really' tells them you did not accept it and that you mean their looks, their name or their accent. People who hear this a lot are tired of it. Ask where they grew up, take the answer you get, and let family history arrive when they offer it.
So where exactly do you live?
Why ask it
From someone they have just met, a request for a street or a building is a safety matter, however innocently it was meant. The side of town is plenty for a first date. Meet at the venue, leave separately, and let the address come when they invite you to it.
Interview
So, tell me about yourself.
Why ask it
It is the opening line of a job interview, and people answer it like one: job title, hometown, a list of hobbies. Nobody knows where to start with a question that wide. Go small and recent: what they did last weekend, or what they would be doing tonight if they weren't here.
So, what do you do?
Why ask it
Fine as a subject and tired as an opener: they have recited the answer to every stranger this year, and asked first it can sound like you are finding their rung on a ladder. Let work arrive on its own by asking what kept them busy this week, then follow whichever part they talk about longest.
Where do you see yourself in five years?
Why ask it
Very few people have a real answer, so you get the one they would give a hiring manager. 'What are you looking forward to this year?' shows whether they have a direction and whether it could sit alongside yours, and it comes with an actual plan you can ask about.
What's your biggest red flag?
Why ask it
Asked of a near-stranger, it gets a rehearsed joke ('I'm too loyal') or an uneasy silence. Nobody hands over their worst trait before the appetizers. How they talk about the waiter, their friends and their week tells you more, and you don't have to ask for any of it.
What do you bring to the table?
Why ask it
It frames the date as an application with you as the one deciding, and the person hearing it either starts selling or starts looking for the door. What they bring shows as they talk: curiosity, humor, whether they ask anything back. 'What are you proud of lately?' is the warm way to hear the rest.
What are your dealbreakers?
Why ask it
A list of dealbreakers on a first date makes the other person check themselves against it for the rest of the night. It is a real conversation for later, once there is something to break. For now, know your own two or three and listen for them: smoking, faith and wanting children tend to surface without being pulled.
Where did you go to college?
Why ask it
Asked early and flatly, it sounds like you are sorting them by credential, and it stings for anyone who did not go or did not finish. 'What was the road to the work you do now?' lets school come up if it is part of the story, and lets a different path be just as good an answer.
What's your love language and your attachment style?
Why ask it
Two labels come back and you know less than you think, because people tend to pick the label they like, and the date starts to feel like an intake form. For the thing underneath, ask about a time: 'What's the nicest thing someone did for you on a bad day?' A story shows what care looks like to them.
About tonight
Do I look like my pictures?
Why ask it
There is one polite answer and you have just made them say it. A real worry about it gets fixed on the profile, with photos from this year, and not across the table. Something like 'it's good to finally hear the voice behind the messages' says you are glad they came without asking for a grade.
What made you swipe right on me?
Why ask it
They now have to produce flattering reasons on the spot, and anything short of a speech sounds faint. Turn it around: name the one thing on their profile that made you want to meet them. A specific compliment usually earns one back.
Are you always this late?
Why ask it
An apology on the way in has already dealt with it, and this reopens it with an 'always' attached. One late arrival tells you about tonight's traffic. 'Was the place hard to find?' lets them explain if they want to, and a real habit will show itself by the third date without your asking.
You seem nervous. Are you okay?
Why ask it
Pointing at someone's nerves doubles them, because now they are nervous and being watched; 'why are you so quiet?' does the same. Own it yourself with something like 'I'm always a bit jittery for the first ten minutes of these,' which gives them company in it. Then ask about something easy, like the menu, and let the shaky hands settle on their own.
Am I your usual type?
Why ask it
They are being asked to line you up next to everyone they have dated and report where you rank. 'Yes' sounds like you are interchangeable and 'no' sounds like a warning. Reassurance is easier to give than to extract: name one thing about them that surprised you tonight.
Are you talking to a lot of other people right now?
Why ask it
On a first date the honest answer is often yes, and nobody owes that to a person they met forty minutes ago. Asking turns the evening into a ranking they did not agree to enter. Save it for the talk about being exclusive, several dates on; tonight, notice whether their attention stays at the table.
How would you rate this date out of ten?
Why ask it
A score asked for to your face will always be polite, so you learn nothing and they feel cornered, and 'so, do you like me?' works the same way. Say your own side, 'I had a really good time,' and let them match it or not. What they do about a second date is the rating.
Are you going to delete the app after tonight?
Why ask it
That is a request for exclusivity as payment for one good evening. Even someone who is very interested will feel the door closing behind them. Leave their phone alone; a few good weeks from now, 'I've stopped looking, how about you?' is the grown-up form of the same question.
How to keep these out of the conversation
Practical guidance for the conversation itself
What makes a date question a bad one
It asks for a record
Most of the questions on this page ask for a number, a date or a history: how many, how much, how long, why it ended. Records invite judgment, and the person answering knows it. A question about what someone enjoys, notices or is looking forward to gives you a person where the record gives you a file.
It is early, not forbidden
Almost nothing here is off limits for good. Exes, money, children and where things are heading are all fair between two people who have decided to keep seeing each other. The trouble is the timing: on a first date the other person has no reason yet to trust what you will do with the answer.
The answer can't win
Test a question by imagining both answers. If a yes makes them look bad and a no makes them look worse, as with 'are you over your ex?', it is a trap whatever you intended. A good first-date question has many answers that would all be fine.
Tone counts, but less than you hope
A smile softens 'why are you still single?' without changing what it asks. If you find yourself putting 'no offense' or 'just curious' in front of a question, treat that as the sign to leave it out.
Finding the version you can ask
Name what you are worried about
Behind nearly every bad date question is a sensible worry. 'How much do you make?' is usually 'will I end up carrying this person?', and 'why did your last relationship end?' is 'are you going to hurt me?' Once the worry has a name, you can see that one number or one story would not have settled it anyway.
Ask about now
Swap history for the present tense. What their week looks like, what they are excited about and who they spend time with are easy to answer, and they tell you most of what the record would have. Many of the swaps under the questions on this page work this way.
Go first
For the things that really are dealbreakers for you, such as wanting children or sharing a faith, say where you stand and stop talking. 'I'd like a family someday' takes five seconds and asks nothing. An offered fact is far easier to respond to than a question that has to be passed.
When there is no early version
A few questions have no first-date form at all: the body count, the salary, the debt, the rating out of ten. Leave them. Some become fair once you are a couple making plans together, and one or two never tell you anything worth the asking.
If one slips out
Take it back in a sentence
'Sorry, that's more than a first-date question. Ignore me.' Then move on. A light retraction shows you noticed, which counts for more than never slipping at all.
Don't explain why you asked
The urge is to justify it: your last partner lied, your friend got burned. That adds your history to their discomfort. Keep the apology short and change the subject to something about them that is easy to talk about.
Answer it yourself, sometimes
With the milder ones, such as how long you have been on the apps, offering your own answer takes the sting out. Do not try it with the heavy ones. Volunteering your own number or your own divorce story only raises the pressure on them to match it.
The day after
If the question hung over the rest of the night, one line in your next message is enough: you enjoyed meeting them, and you are sorry for prying about the ex. Then leave it with them.
When your date asks you one
You can decline kindly
'Ask me that on date four,' said with a smile, is a complete answer. So is 'that's a longer story than this drink.' Neither is rude, and a date who keeps pushing after either one has told you something useful.
Answer the worry instead
If you can hear what they are after, speak to that. To 'why are you still single?' you might say you have been picky and busy, and that you are glad to be out tonight. They get the reassurance and you keep your history.
A short true answer, then turn it
For the ones you do not mind, two sentences and a question back keep the evening moving: 'It ended about a year ago, no drama. What have you been up to this year?' You decide how much is in the two sentences.
One clumsy question is not a verdict
Nervous people ask bad questions. A single one, dropped as soon as you deflect it, says little about the person who asked. A run of them, or one repeated after you have declined, is worth weighing when you decide about a second date.