Yes or No Questions to Ask
Yes or no questions about things people have actually done, chosen for the stories that arrive with the answer. Useful for icebreakers, long drives and getting past small talk without asking anything heavy.
The questions
Open any question for the note
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.
Getting more than one word back
Practical guidance for the conversation itself
How to run these
Pick three, not twenty
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.