Random Questions to Ask
Random questions to ask people when the conversation has stalled and you want something, anything, that is not about work or the weather. They run from quick and weird through favorites and hypotheticals to a few thoughtful ones, and one group is random questions to ask your friends, the kind that need some history behind them. Every question has a note on what it tends to bring out, so you can pick one on purpose or leave it to chance.
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The questions
Each question, and why to ask it
Quick
Window seat or aisle seat, and why is the other choice wrong?
Why ask it
Gets an answer in one second and a defense in ten. Window people talk about the view, aisle people about freedom. The rare middle-seat volunteer deserves a follow-up of their own.
What was the last thing you wrote down by hand?
Why ask it
A shopping list, a birthday card, a phone number on the back of an envelope. The answer shows where pen and paper still earn a place in someone's day, and some people need a moment to remember. Ask whether they can read their own handwriting.
What song was most recently stuck in your head?
Why ask it
Quick to answer and mildly revealing, since nobody chooses what gets stuck. Be aware that naming the song tends to pass it on, so you may be humming a jingle for the rest of the day.
Do you take the first parking space you see or circle for a better one?
Why ask it
A tiny decision that shows how someone weighs good enough against perfect. First-space people like being done, and circlers are sure a better spot is one row closer. Passengers have opinions on this too, so non-drivers can join in.
What did you have for breakfast today, and was it a decision or an accident?
Why ask it
The second clause lifts it above small talk. You find out who plans their mornings and who ate crackers over the sink. Handy early in the day, when the memory is fresh.
Do you make your bed every day, sometimes or never?
Why ask it
Three options make it easy to answer honestly. Daily bed makers usually have a reason they are keen to share, and the never camp has a philosophy too. Let each side explain.
What is the wallpaper on your phone, and how long has it been there?
Why ask it
Shows what someone chooses to look at many times a day: a person, a place, or the default they never changed. Each of those three answers says something different about them.
Stairs or elevator when it is only two floors up?
Why ask it
People make this tiny decision without thinking, which is why it is interesting to say out loud. Listen for the conditions: only if nobody is watching, only if carrying nothing.
What color do you wear more than any other?
Why ask it
Most people can answer by looking down. Ask whether it was a choice or something that crept up on them. Those who say black will often explain it as a time-saving strategy.
Do you read the instructions first, or only after something goes wrong?
Why ask it
Tells you quickly how someone approaches anything new, from furniture to board games. Useful to know before you build a shelf or learn a card game with them.
Roughly how many unread messages or emails are waiting for you at this moment?
Why ask it
The number divides people into those who keep it at zero and those with a five-digit badge they have stopped seeing. Each side finds the other alarming. Ask them to check for accuracy.
Text message, phone call or voice message?
Why ask it
Practical as well as quick, since you learn how this person prefers to be reached. Voice messages draw strong feelings in both directions. Ask what they do when the phone rings unexpectedly.
Do you squeeze out the very last of the toothpaste or open the new tube early?
Why ask it
A small thrift test. Some people flatten the tube with a comb, others have two tubes open at once and feel nothing. Households often contain one of each, and both know exactly who they are.
What book is physically closest to you right now?
Why ask it
Asks for a fact and not a favorite, so nobody has to perform good taste. The answer might be a cookbook, a manual or something borrowed and never returned. Ask how long it has sat there.
Are you a list maker, or do you keep it all in your head?
Why ask it
List makers will happily show you the list. The others will explain a system that sounds precarious. Follow up by asking what the last thing they forgot was.
Cold room with heavy blankets or warm room with a light sheet?
Why ask it
Sleep preferences are personal without being private, which makes them good quick material. Anyone who shares a bed will have a story about negotiating this one.
What is the last thing you lost, and did it ever turn up?
Why ask it
Keys, a single glove, an umbrella left in a cafe. The second half is where the story is, since lost things resurface in coat pockets and other people's cars months later. Anyone who never loses anything will tell you so with some pride.
What is your order when you cannot be bothered to read the menu?
Why ask it
Reveals the default setting: the safe dish someone falls back on everywhere. It tells you if they are adventurous with food or loyal to one thing. Useful before choosing a restaurant together.
Which would you give up first for a month: music, sweets or your favorite show?
Why ask it
A forced choice with no right answer, quick to make and interesting to defend. The thing they refuse to give up is the real answer. Ask how long they think they would last.
What one word would your closest friend pick to describe you?
Why ask it
Still quick, but it asks for a little self-awareness, so place it last in a fast round. People often choose a word and then argue with it. If the friend is present, check the answer.
Weird
What noise does your home make that would worry a guest but no longer worries you?
Why ask it
An easy way into odd territory, since the answer is strange and completely harmless. The pipe that knocks, the fridge that sighs, the stair that answers back. People stop hearing these until a visitor asks. Find out whether the noise has a nickname.
What word stops looking like a real word when you stare at it for too long?
Why ask it
Everyone has had this happen and few have talked about it. Ask them to spell the word out loud and watch it happen again in real time. Good for people who like language.
What is the oddest thing you collected as a kid?
Why ask it
Children collect without shame: bottle caps, erasers, interesting gravel. Ask where the collection is now. Plenty of them are still in a box at a parent's house, awaiting a decision.
What is the strangest thing you have ever been woken up by?
Why ask it
A safe kind of weird that anyone can answer. The stories involve animals, neighbors, hotel fire alarms and siblings with a plan. Ask what they thought was happening in the first few seconds, which is usually the better half.
What is a texture you absolutely cannot stand to touch?
Why ask it
Reactions are physical and immediate, and people shudder just naming theirs. Chalk, velvet and wet paper are common culprits. Do not produce the texture in question. It is not as funny as you think.
What smell do you like even though you know you are not supposed to?
Why ask it
A mild confession that finds allies quickly. Fresh markers, a hardware store, rain on hot pavement. When two people share the same odd answer, they tend to bond over it on the spot.
Do you see faces in everyday objects, and is there one you have quietly given a name?
Why ask it
Sorts people into those who see a worried expression on every power outlet and those who have no idea what you mean. The naming part is where the committed ones give themselves away.
What ordinary object do you find slightly creepy for no good reason?
Why ask it
Slightly is the important word, since it keeps real phobias out of it. Porcelain dolls are expected. The interesting answers are things like revolving doors or an empty swing still moving.
What is your strangest habit when you are concentrating hard?
Why ask it
Someone close to the person can often answer better than they can, so it works well with pairs. Tongue out, humming, pacing. Most have no idea they do it until somebody points it out.
What were you afraid of as a child that seems ridiculous now?
Why ask it
Childhood fears have their own logic: the bathtub drain, a particular cartoon, the hallway at night. Ask what they did to protect themselves, since there was always a system.
What is the oddest thing you put on toast, rice or noodles when nobody is judging?
Why ask it
Naming three plain foods makes it concrete and gets a real answer. The defensive tone people use is part of the pleasure. Occasionally someone's odd combination turns out to be worth trying.
What is the strangest thing you have ever found on the ground and kept?
Why ask it
Separates the people who pick things up from the people who are horrified by that. The keepers can usually tell you where the object is right now. Ask what they imagine its story was.
What superstition do you follow even though you know it makes no sense?
Why ask it
Few people call themselves superstitious and nearly everybody has one ritual. Athletes and performers often have the most elaborate. Ask what happened the one time they skipped it.
What is the strangest rule you have ever seen posted on a sign?
Why ask it
Every odd sign implies that somebody once did the thing it forbids, and that is the conversation. Speculating about the incident behind the sign is more fun than the sign itself.
What can you do with your face, hands or voice that most people cannot?
Why ask it
A physical party trick question, so expect demonstrations: ear wiggling, odd finger joints, a convincing bird call. It needs a relaxed setting. Less suitable for a video call with a manager present.
What animal do you suspect knows more than it is letting on?
Why ask it
Crows, octopuses and cats lead the suspect list. The question gives people permission to float a theory they half believe. Ask what they think the animal is waiting for.
What inside joke do you share with someone that would sound unhinged if you explained it?
Why ask it
The attempt to explain is the entertainment, and it nearly always collapses halfway through. What you really learn is who their person is and how far back the two of them go.
Which everyday activity of ours will look bizarre to people a few centuries from now?
Why ask it
A weird question with a thoughtful edge. People nominate mowing lawns, neckties and commuting. It is a polite way of learning what someone already finds absurd about ordinary life.
If the inside of your head were a room, what would it look like right now?
Why ask it
The hardest of the weird ones, and the most revealing. A tidy library, a garage full of boxes, a room with every light on. 'Right now' keeps it about today and not their whole personality.
Favorites
What is your favorite mug, bowl or plate, and would you notice if it went missing?
Why ask it
Nearly every kitchen has one item that is quietly somebody's. The second half gets a laugh, because the honest answer is that they would notice within the hour. Ask where it came from.
What is your favorite kind of weather to be indoors during?
Why ask it
More specific than asking about favorite weather, and it gets a whole scene: the rain, the window, the blanket, the book. A cozy one for small groups and for people who dislike being put on the spot.
What is your favorite number, and does it have a story or did it just show up?
Why ask it
Sounds like a question for a six-year-old, which is part of the appeal. Some numbers come from a jersey, a birthday or an old house, and others have no explanation at all. Ask whether they actually use it for anything, like a seat or a locker.
What is your favorite word to say out loud, purely for the way it sounds?
Why ask it
Removes meaning from the equation and leaves pure sound, so the answers are words like 'plinth' and 'rhubarb'. Have them say it twice. Suits writers, kids and anyone who reads aloud.
What is your favorite thing to listen to on a long drive?
Why ask it
Covers music, podcasts, audiobooks and silence, and the choice tells you how they like to spend time alone. Ask if the answer changes when there is a passenger.
What is your favorite season, and which exact week of it is the best?
Why ask it
The exact week is where it gets good. People will describe the first cold morning or the week the lilacs open with a precision they did not know they had.
What is your favorite movie to rewatch when you are sick or sad?
Why ask it
A comfort film is a different thing from a favorite film, and people will happily explain the distinction. You learn what soothes them. Make a note of it for the next time they are ill.
What was your favorite game as a kid that needed no equipment at all?
Why ask it
Brings back the rules of games invented on staircases and playgrounds, often with names that made sense to four children and nobody else. Ask them to explain the rules. They will struggle.
What is your favorite way to spend the first hour of a day off?
Why ask it
Narrowing it to the first hour gets a real routine in place of a fantasy itinerary. Coffee in silence, a long run, going straight back to sleep. It shows what rest means to them.
What is your favorite tree, flower or plant, and where did you first notice it?
Why ask it
Not a favorite people are often asked for, so the answer arrives unrehearsed. A favorite plant tends to come attached to a place: the tree outside a classroom window, tomatoes on a grandparent's balcony. Follow the place and you will hear about the people who were there.
Which fictional character would be your favorite to have as a next-door neighbor?
Why ask it
The neighbor condition rules out heroes who attract explosions. People start weighing who would lend a ladder and keep the noise down, and the practical turn is where the fun starts.
What is your favorite place to sit and do absolutely nothing?
Why ask it
Most people have a spot: a porch step, a particular bench, the parked car before going inside. Asking about it treats doing nothing as worthwhile, and people tend to appreciate that.
What is your favorite walk, the one you would take a visitor on?
Why ask it
Asks for a favorite and a small act of hospitality at once. People describe the route turn by turn, which says a lot about what they notice. If you are local, offer to be the visitor.
What is your favorite meal that only one specific person can make properly?
Why ask it
The dish is rarely fancy and the recipe never quite works for anyone else. You will hear about the cook more than the food. Be gentle, since that person may no longer be around.
What was your favorite book as a child, and have you dared to reread it?
Why ask it
The 'dared' acknowledges a real risk, which is that some childhood favorites do not survive a second reading. Parents who have read theirs aloud to their own kids have the best verdicts.
What is the favorite piece of clothing you have ever owned, and what became of it?
Why ask it
There is always a jacket or a pair of boots that got away. The fate of the item is the story: lost on a train, shrunk in the wash, borrowed by a sibling and never seen again.
Which teacher was your favorite, and what did they do that the others did not?
Why ask it
Asking what they did differently gets a specific memory and not a vague tribute. Often it was one small thing, like being taken seriously. A good question for anyone who now teaches or manages people.
What is your favorite thing about the place you grew up, now that you have some distance from it?
Why ask it
'Some distance' gives people room to be fair to a place they may have been keen to leave. Answers tend to be small: the light, a bakery, knowing everyone. Skip it with anyone for whom home is a hard subject.
What is your favorite thing about your closest friend that they would be surprised to hear?
Why ask it
Turns a favorites question into a compliment waiting to be delivered. It is rarely the obvious trait. Suggest they pass it on to the friend, since that step tends to get skipped.
Hypothetical
If you could have any view from your bedroom window, what would you wake up to?
Why ask it
Gentle and visual, so it suits people who dislike big hypotheticals. Ocean, skyline, a field with one horse. Notice whether they pick somewhere they have been or somewhere they have only imagined.
If you could instantly master one musical instrument, which would it be and where would you first play it?
Why ask it
Where they would play separates the people who want an audience from the ones who want to play alone in the kitchen. Cello and drums attract very different personalities, and both will explain why.
If you could have dinner anywhere in the world tonight, with the travel taken care of, where would you go?
Why ask it
Tonight keeps it concrete, so people think about a real table and a real dish. Some pick a famous city, others a relative's kitchen far away. The second kind of answer deserves a follow-up.
If you had a lifetime supply of one ordinary thing, what would save you the most hassle?
Why ask it
Ordinary is the constraint that makes it interesting. People choose socks, stamps, olive oil, phone chargers. The answer is a precise map of the small errands they resent.
If you were handed the keys to any vehicle for a weekend, what would you drive, sail or fly?
Why ask it
The weekend limit keeps it playful, since nobody has to pay for fuel or find parking for a hot air balloon. Some go for speed, others for a camper van and a slow road. Ask who they would bring along and where they would point it.
If you had to eat one cuisine for an entire year, which would you get tired of last?
Why ask it
'Get tired of last' is a more honest test than 'favorite', since it rewards variety over one great dish. People reason out loud about breakfasts, which is where most cuisines get cross-examined.
If your home could have one feature borrowed from a hotel, which would you pick?
Why ask it
Blackout curtains, a bed that gets made while you are out, breakfast waiting downstairs. The pick shows which part of looking after a home someone would most like to hand off, or which small comfort they never get around to arranging for themselves.
If your home had a secret passage, where would it start and where would it lead?
Why ask it
Appeals to the child in everyone. The practical ones link the bedroom to the kitchen, the romantics go from a bookcase to a hidden garden. Ask who else would be allowed to know about it.
If you could get a guided tour of any building that is closed to the public, which would you choose?
Why ask it
Curiosity with a locked door in front of it. Some people name a vault or a palace, others the shuttered factory they pass every day. The local answers are often the better ones. Ask what they expect to find inside.
If a stranger offered to pay for any class you wanted, what would you sign up for?
Why ask it
Removes cost, which is the usual excuse, and leaves curiosity. Pottery, welding, sailing and sign language come up a lot. Ask what is really stopping them, since it is rarely only the money.
If every job paid exactly the same, which one would you apply for on Monday?
Why ask it
Monday makes it practical and not a daydream. Some people describe their current job, which is good news. Others describe a bakery or a national park, which is worth talking about.
If you were given a plot of land and told to build anything except a house, what would you put there?
Why ask it
Ruling out the house forces imagination. A maze, an orchard, a tiny cinema, a dog park. Notice whether what they build is for themselves or for other people to use.
If you could swap lives with someone you know for a single day, who would it be and what would you check first?
Why ask it
'Someone you know' keeps it grounded, and 'what would you check first' adds mischief. The usual curiosity is about a sibling's or a friend's ordinary day, which shows how little of each other's lives we see.
If you could know the complete history of one object you own, which would you choose?
Why ask it
Best with people who own something old or secondhand: a ring, a guitar, a used book with an inscription. The guesses they make about the object's past are half the conversation.
If you had to move to a country you have never visited, which would you pick and what would you miss most?
Why ask it
A two-part answer that balances curiosity against attachment. What they would miss tends to be small and specific, like a certain grocery store or a Sunday habit, and it says more than the country does.
If you could see one lifetime statistic about yourself, which would you ask for?
Why ask it
Hours spent waiting in line, how far they have walked in total, the count of times they have said sorry. The number someone picks shows what they suspect has quietly taken up their life. Ask whether they are hoping it is higher or lower than they fear.
If a park bench, a pasta shape or a side street were named after you, which would you pick?
Why ask it
Recognition on a small scale, with the pressure of real fame taken off. Bench people want to be useful, street people want to last, and pasta people want to be enjoyed. Ask where the bench or the street would be, and what the plaque would say.
If you could watch any one thing being made from start to finish, what would you want to see?
Why ask it
A violin, a cathedral, a croissant, a favorite album. The choice shows what someone finds quietly impressive, and whether they are drawn to patient handwork or to huge projects with many people. Works with children too, who might pick crayons or a fire engine.
If you had to delete every photo you own except one, which one would you keep?
Why ask it
The hardest of the hypotheticals, so give it time. People scroll in their minds and usually land on a photo of a person, often an unremarkable shot. Ask them to describe it, and do not rush them.
Friends
How am I saved in your phone, and has the name ever changed?
Why ask it
Most contacts are a plain first name, and the exceptions have a story: a nickname from one bad karaoke night, a surname nobody uses, an emoji with a history. Friends tend to demand the screen as proof, so expect phones to come out.
What is the most random fact you know about me?
Why ask it
Friends store odd details about each other: a shoe size, a fear of geese, the sandwich order from one road trip. Hearing which detail stuck is flattering in a sideways fashion. In a group, pick one person and let everybody supply a fact.
What do I always order, say or do that you could predict with your eyes closed?
Why ask it
Being predictable to a friend is a sign of time served. The impressions that follow are affectionate and uncomfortably accurate. Let the person being described rule on whether each one is fair.
What have I recommended that you ended up liking, and what did you quietly give up on?
Why ask it
Two answers, one kind and one honest. People press shows, books and restaurants on their friends for years without hearing a verdict. Take the second half with good grace, since you asked for it.
What do you imagine I was like at ten years old?
Why ask it
Works best between friends who met as adults, because the guess has to be built from who you are now. Bossy, shy, covered in mud. Correct the record afterwards, with a school photo if one is within reach.
If the two of us opened a shop, what would it sell and who would deal with the customers?
Why ask it
The product says what the friendship runs on, be it plants, snacks or secondhand records. The division of labor is the sharper half, since both of you already know who is good with strangers and who belongs in the back with the stock.
What is something I own that you have always wanted to borrow?
Why ask it
A jacket, a cast iron pan, a tent that has seen one outing. It is a compliment to your taste and a small confession at once. Lending the thing on the spot is a good way to end the answer.
Which errand or dull afternoon with me turned out better than it had any right to?
Why ask it
A lot of friendship happens in unplanned hours, like a run to the hardware store or a wait for a delayed train. Asking for a dull occasion skips the birthdays and holidays anyone would name. You may find the two of you remember different afternoons.
What habit, phrase or taste have you picked up from me?
Why ask it
Friends rub off on each other, and neither usually notices until somebody points it out. A word they now overuse, a way of loading the dishwasher, a band they once mocked. Be ready to admit what you took from them in return.
What have you never asked me because you assumed you already knew the answer?
Why ask it
Old friends stop asking each other the basics, which is how you can know someone for a decade and still be unsure of their middle name. Whatever comes out, answer it properly. It often starts a round of simple questions in both directions.
Thoughtful
Who did you last have a really good conversation with, and what was it about?
Why ask it
Gentle for a thoughtful question, since it asks for a recent memory and not an opinion. The answer tells you who they open up to and what holds their interest. If they have to think back a long way, that is worth a kind follow-up.
What have you started doing lately that you wish you had started years ago?
Why ask it
Shows what is new in someone's life at the moment, and the answer can be as small as stretching in the morning or writing things down. The regret in it is a mild one, so people answer cheerfully. You may come away with a habit worth borrowing.
What part of your daily routine would you miss most if it disappeared?
Why ask it
People find out what they value by imagining it gone. The school run, the dog walk, the first coffee. It turns an unexamined habit into something they are briefly grateful for.
What does a really good ordinary day look like for you, from start to finish?
Why ask it
'Ordinary' rules out vacations and birthdays, so you get a picture of a life they could have more often. Listen for how much of it involves other people and how much is solitude.
What is the most useful thing anyone taught you in under five minutes?
Why ask it
Practical by design: how to chop an onion, how to end a phone call. People are glad to pass the lesson on, so you might learn something. Credit usually goes to a grandparent or a first boss.
What did you spend a lot of time on as a teenager that turned out to be useful?
Why ask it
Hours on video games, band practice, fixing a bike or arguing online rarely looked like preparation at the time. People enjoy tracing the line from that to something they can do now. Some will be making the connection for the first time as they answer.
What did you once worry about constantly that turned out not to matter?
Why ask it
Reassuring to answer and to hear. It works well with someone who is currently worried about something, provided you let them make the connection themselves.
What have you never been able to throw away, and why does it stay?
Why ask it
Objects are an easier way into feeling than feelings are. A ticket stub, a broken watch, a child's drawing. Ask where it is kept, since the hiding place is often part of the story.
What is something you are better at now than five years ago that has nothing to do with work?
Why ask it
Excluding work makes people look at the rest of their life, where progress goes unrecorded. Saying no, cooking, being on time, staying in touch. Give them a moment, since few people keep track of this.
What skill did you give up on too early?
Why ask it
Piano, a language and drawing are the usual regrets. The follow-up is whether they would start again now and what stops them. Sometimes saying it out loud is the nudge they needed.
What is the best decision you made that looked like a mistake at the time?
Why ask it
Vindication is a story people enjoy telling. Quitting something, moving somewhere, saying no. Ask who doubted them, and whether that person ever admitted they were wrong.
What did you learn from a person you did not much like?
Why ask it
Demands fairness toward a difficult person, which takes some maturity. The lessons are often about what not to do, and that counts. Best one on one, where nobody needs to be diplomatic.
Which friend do you wish lived closer, and what would the two of you do if they did?
Why ask it
The second half is the thoughtful bit. The plans people describe are rarely grand: a weekly walk, dinner on a Tuesday, sitting in the same room doing nothing. It shows what they miss about the friendship, and it may prompt them to get in touch.
Who outside your family shaped you the most, and do they know it?
Why ask it
A coach, a neighbor, a friend's parent, a boss. The closing clause has a way of sending people off to write a message they have owed for years. Ask it when there is time to hear the whole answer.
What did your parents or guardians get right that you only appreciated later?
Why ask it
A generous framing that still leaves room for complicated families. People mention bedtimes, chores and being made to write thank-you notes. Skip it if you know the subject is painful for them.
What risk did you not take that you still wonder about?
Why ask it
Heavier than it looks, so keep it for a quiet setting and someone you know reasonably well. Let them decide how far to go. Wondering is not the same as regretting, and the difference is a good follow-up.
What do you think people most often get wrong about you?
Why ask it
Gives someone a chance to correct the record. Quiet people get read as cold, funny people as never serious. Listen without arguing, even if you hold the misreading yourself.
What question have you been asking yourself lately?
Why ask it
A fitting last question, since it hands the asking over to them. Some will joke about dinner, others will tell you what is really on their mind. Either is fine. Leave a long pause after asking it.
How to ask a random question without it feeling random
Practical guidance for the conversation itself
Asking out of nowhere
Flag the change of subject
A question with no lead-in can sound like a test. Say 'random question' or 'this has nothing to do with anything' first. Those few words tell the other person that a playful answer is welcome and that nothing is being measured.
Let chance do the choosing
The list is more fun when nobody controls it. Have someone call out a number, scroll with eyes closed, or let the youngest person point. A question picked by luck carries no agenda, so people answer it more freely.
Climb from Quick to Thoughtful
Quick questions cost nothing to answer, which makes them the right place to begin. Move to Weird and Favorites once the answers start getting longer without prompting, and keep Thoughtful for when the conversation has slowed down and nobody is checking the time.
Treat the list as a starting point
If an answer about a favorite mug turns into a story about a grandmother, stay with the grandmother. The goal is a conversation, and the next question on the list will still be there later.
Ways to use the list
Pick a number
- 1Ask someone to choose a number without seeing the list.
- 2Count down to the question in that position, read it out and have them answer it.
- 3They then choose the number for the next person.
- 4Anyone may trade their question once for the one directly after it.
One a day
- 1Choose one person or one group chat.
- 2Send a single question each day at about the same time, and answer it yourself first.
- 3Work through the tags in order across the week, so the questions deepen gradually.
- 4Drop the routine for a few days if replies start to feel like homework.
Question jar
- 1Copy a mix of questions from every tag onto slips of paper and fold them.
- 2Keep the jar on the dinner table or in the car.
- 3Draw one slip per meal or per trip, with a different person drawing each time.
- 4Put back the slips that worked well and retire the ones that did not.
Walk and talk
Thoughtful questions are easier side by side than face to face. Carry a couple in your head on a walk or a drive, ask one when there is a natural gap, and let the silences run. Nobody has to hold eye contact while they think.
Adjusting and recovering
When every answer is one word
Short answers usually mean the question was too big too soon, or the person is not sure how much you want to hear. Drop back to a Quick question, give a longer answer of your own, and try 'why that one' before reaching for a new question.
When it starts to feel like an interview
A run of questions with nothing offered in return is an interrogation. Answer each one yourself, react to what you hear, and invite the other person to pick the next question for you.
When a light question lands heavy
A question about a favorite meal can lead to someone who has died. Do not change the subject in a panic. Listen, thank them for telling you, and let them decide whether to stay with it or move on.
With kids, coworkers and new acquaintances
Children do best with Weird and Hypothetical questions and lose patience with Thoughtful ones. At work, stay with Quick and Favorites unless you know the person well. With someone new, leave family questions alone until they bring family up themselves.
Random questions to ask a guy or a girl you like
Nothing on the list is written for one gender, so what to send depends on how well you know the person and not on who they are. Over text, start with Quick and Favorites, which can be answered in a line between other things, and put your own answer in the same message so it reads as chat and not a quiz. Bring in Weird and Hypothetical once the replies are coming back fast, leave Friends until there is some shared history to ask about, and keep Thoughtful for when you are talking in person.