Yes or No Questions to Ask
Yes or no questions about what people have done, what they can do and the small habits they keep, chosen for the stories that arrive with the answer. Useful for icebreakers, group warmups, long drives and first meetings, with a few more searching questions held for the end.
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The questions
Each question, and why to ask it
Have you lived here your whole life?
Why ask it
Both answers open a door: a yes leads to how the place has changed, a no leads to why they came. Easier to answer than "where are you from," which some people find loaded.
Do you have a passport?
Why ask it
A practical question that sidesteps the assumption in "do you travel much," which can land badly on someone who cannot afford to. The expiry date usually comes up unprompted, along with plans.
Have you ever traveled somewhere on your own?
Why ask it
Solo travel produces sharper stories than group trips, because everything that went wrong was theirs to solve. A no often comes with an admission that they would like to, which is the more interesting thread.
Did you have a nickname growing up?
Why ask it
Ask whether they liked it, because that is where the story is. Some people will not repeat the nickname, and that reluctance is worth respecting rather than pressing.
Do you know how to change a tire?
Why ask it
Splits a group in a way that has nothing to do with age or gender, and the yeses usually learned in a specific, memorable situation. The nos tend to have a roadside story anyway.
Have you ever been on a stage in front of an audience?
Why ask it
Covers school plays, bands, weddings, best man speeches and work presentations, so almost everyone has something. Ask what the audience was, because the number changes the story completely.
Did you keep anything from your childhood bedroom?
Why ask it
The objects named are almost never valuable, which is what makes the answer good. A no often means a move or a family change and should be followed gently.
Have you ever quit something you were good at?
Why ask it
One of the few light questions that reliably produces a real answer, usually about an instrument or a sport. Notice whether they still sound sure about the decision.
Do you still talk to anyone you knew before you were ten?
Why ask it
A yes is unusual enough to be a story on its own, and a no is completely ordinary and says something about how much their life has moved. Do not treat either as the better answer.
Have you ever cooked for more than ten people?
Why ask it
Gets at competence and family role rather than taste, and it usually surfaces a holiday disaster. The scale in the answer, ten versus a hundred, tells you what kind of household they came from.
Have you ever had a job you would refuse to do again?
Why ask it
Safer than asking about the worst job, since it lets people choose what to reveal about work they are not proud of. The refusal is the interesting part, so ask what specifically made it a no.
Have you ever been properly lost?
Why ask it
The word properly rules out the small everyday version and gets the real story, often from before phones had maps. Expect a location, a stranger and a lucky turn.
Do you know what your parents were doing at the age you are now?
Why ask it
Quietly one of the strongest questions in the set, because the comparison usually lands while they are answering. A no is common and often becomes a conversation about what they never asked.
Have you ever been in a car that broke down far from home?
Why ask it
Almost universal, and it produces a story with a place, a wait and someone who helped. Good for filling actual travel time, since the setting matches.
Did you ever keep a diary?
Why ask it
The follow-up worth asking is whether they still have it and whether they could bear to read it. A surprising number of people have destroyed one, which is a better answer than keeping one.
Have you ever changed your mind about something you had argued for?
Why ask it
The deepest question here while still being answerable with one word, so hold it until people are comfortable. Anyone who says never is telling you something either way.
Have you ever been to a wedding where something went wrong?
Why ask it
Reliable in almost any group, and the stories improve with distance from the event. Steer away from anything involving people at the table, which is how this one occasionally goes wrong itself.
Do you have a scar with a story behind it?
Why ask it
The qualifier matters: it invites the story rather than asking anyone to display anything. Drop it immediately if the answer relates to illness or an injury they would rather not discuss.
Have you ever spent a night somewhere you would not repeat?
Why ask it
Wide enough to include hostels, airports, tents, sofas and hospital chairs, so people choose their own comfort level. The airport answers are funny and the others are worth listening to properly.
Would you take a job in a city you had never visited?
Why ask it
The only hypothetical in the set, which is why it closes it out. The instant answers are the informative ones, and the reasons behind a no usually name whatever is keeping them in place.
Do you drink coffee?
Why ask it
A deliberately low-stakes opener whose only job is to get someone talking, and it works because everybody has an answer ready. The useful part is the follow-up, since how someone describes their morning drink usually leads straight into how their mornings actually go.
Do you make your bed most mornings?
Why ask it
Divides a room instantly and harmlessly, and both sides feel mildly superior. The interesting answers are the people who changed sides at some point and can say when.
Do you set more than one alarm?
Why ask it
The number is the whole story: two is normal, five is a personality. Ask whether they get up on the first one, since the honest answer is often no.
Do you answer calls from numbers you do not recognize?
Why ask it
One of the sharpest generational splits you can ask about without mentioning age. The follow-up worth asking is what they do instead, because the workarounds are elaborate.
Do you reply to messages as soon as you read them?
Why ask it
A live issue for anyone who works in the same group, so expect some pointed laughter. Ask how long an unanswered message can sit before it becomes a problem, and watch the numbers diverge.
Do you sing in the car?
Why ask it
Safer than asking whether someone can sing, and the yes usually names a specific song. Watch for the people who only do it alone, which is a different and funnier answer.
Do you finish books you are not enjoying?
Why ask it
A small ethics question dressed as a habit, and people have surprisingly firm positions. The yeses often describe it as an obligation, which is worth following.
Do you remember people's names on the first try?
Why ask it
Useful in a group because the honest no gives everyone else permission to forget too. The yeses usually have a trick, and it is worth asking them for it out loud.
Do you say hello to dogs on the street?
Why ask it
Gets a yes from people who have been quiet all evening, which is its main use. The ones who ask the owner first are a distinct and identifiable type.
Do you cry at films?
Why ask it
Almost always produces a title, which is the better half of the answer. Notice who says no immediately and then names the exception thirty seconds later.
Do you talk to strangers on planes?
Why ask it
Reveals how someone handles enforced proximity, which is closer to real social preference than asking whether they are shy. The strategies people use to avoid it are the funniest part.
Do you tell people when they have something in their teeth?
Why ask it
Sorts a group faster than any personality question, because both positions are defensible and both sides think theirs is the kind one. The follow-up is where the line sits: a colleague, a stranger, a boss.
Do you have pets?
Why ask it
One of the few questions that reliably makes a guarded person animated, and a no is just as informative as a yes when you ask why not. Watch for the answer that arrives with a story about a pet that has died, which is a sign the conversation can go deeper than you expected.
Do you have brothers or sisters?
Why ask it
One of the few closed questions that opens a whole area, since the answer usually comes with numbers and birth order. Be ready for a complicated family answer and let the person decide how much to explain.
Can you drive a manual car?
Why ask it
This is a skills question disguised as small talk, and it tends to reach the person who taught them, usually a parent, a grandparent or a first job. It also works well across ages, since the answer says something about where and when someone learned to drive.
Do you know how to swim?
Why ask it
A surprisingly revealing question, because whether someone was taught to swim tracks closely with childhood access to pools, lessons and vacations. A no is often accompanied by a specific reason, so ask gently and do not treat it as a gap to be corrected.
Can you cook something without a recipe?
Why ask it
More revealing than asking whether someone likes cooking, because it asks about capability rather than taste. The yes almost always names the dish without being asked.
Are you good at keeping plants alive?
Why ask it
Both camps have a story ready: the person with forty houseplants, and the person who has killed the same succulent three times. A rare closed question where a flat no is funnier than a yes.
Are you afraid of heights?
Why ask it
Fear is easier to admit in a yes or no format than in a story, which is why this works better than asking what scares them. Do not chase it with a plan to cure it, just ask when they last noticed it.
Have you ever broken a bone?
Why ask it
Reliable in a group because the answers arrive as stories rather than facts, and children and adults enjoy it equally. Notice that a long pause before the yes usually means the story involves something they did to themselves.
Do you remember your first day of school?
Why ask it
A genuine split: some people have a clear image and some have nothing at all. The nothing-at-all answers are interesting too, so do not treat a no as a dead end.
Have you ever met someone famous?
Why ask it
The yes is a story you would otherwise never hear, often involving an airport or a restaurant. Nos frequently produce a near-miss story anyway, which is usually better.
Do you still use anything you owned ten years ago?
Why ask it
Gets past preferences into actual habits, and the objects named are usually unglamorous: a jacket, a pan, a bike. A no is worth following, because it often means a move or a big change.
Have you ever lived on your own?
Why ask it
A quiet question that reaches independence, money and whether they liked their own company. The interesting follow-up is whether they would do it again, since the answer separates people who found it freeing from people who found it lonely.
Have you ever quit a job with nothing lined up?
Why ask it
This gets at risk appetite through something that actually happened rather than through a hypothetical. A yes usually comes with the reason it became unbearable, and a no often comes with the time they nearly did, which is just as revealing.
Have you ever been in a long-distance relationship?
Why ask it
Concrete rather than intrusive, and it moves the conversation toward relationships without asking anyone to summarize their history. The useful follow-up is what made it workable or unworkable, since people describe their own needs while answering.
Do you like where you live?
Why ask it
Most people say yes, so the speed of the answer carries more than the word does: a hesitant yes usually points at something they have not decided whether to mention. Safe as an opener, since nobody has to reveal more than they planned.
Would you move back to the place you grew up in?
Why ask it
This one usually gets an instant yes or no and a strong reason, which is exactly what you want. Listen for whether the reason is the place or the people, since that distinction tells you a lot about how someone thinks about home.
Do you think people can change?
Why ask it
A yes or no that opens directly onto how someone reads their own family, their exes and themselves. Almost everyone gives the answer they need to be true, so the reason matters far more than the word.
Are you happier than you were five years ago?
Why ask it
The closer, because it makes someone actually compare rather than report a mood. A long silence before the answer is the most honest response you can get, and the right next move is to wait rather than to fill it.
Getting more than one word back
Practical guidance for the conversation itself
How to run these
Pick three, not fifty
A list read out in order becomes a quiz. Choose the two or three that suit the person and the setting, and let the conversation leave the list as soon as it wants to.
Ask for the specifics, not the reason
"Where was that?" and "how old were you?" produce a story. "Why?" asks someone to justify themselves and often gets a shrug.
Answer your own question
Say your version after they answer, briefly. It converts an interview into an exchange and gives them a sense of how much detail is welcome.
Where these work
- Long drives and trains, where nobody has to hold eye contact.
- Dinner with people who half know each other and have run out of shared topics.
- Waiting rooms and delays, where a light question passes real time.
- A first meeting where an open question would feel like too much.
- Family gatherings, since older relatives answer experience questions readily.
- Any group where one or two people have not spoken yet.
Where this goes wrong
Treating a no as a failure
Plenty of people have never been on a stage or kept a diary, and following a no with visible disappointment makes them work to entertain you. Move on cheerfully.
Questions that assume money
Travel, passports and holidays all presume resources. Keep them plain, avoid asking where someone went last summer, and drop the topic if it is clearly not theirs.
Chasing the story they stopped telling
A short answer to the scar, diary or job questions is a boundary rather than shyness. Ask the next question instead of the follow-up.