Questions to Ask Your Crush
These are questions to ask someone you like but do not know well yet, whether you sit near them in class, share a shift or mostly talk by message. None of the 150 depends on who is asking or on whether you want to get to know him or her, so they fit a girl crush as well as a guy. They are grouped as Openers, Getting to know them, Funny, Flirty, Over text and Deep, and each has a note on what the answer tells you, what to ask next or when to leave it alone. Flirty here means playful, and both Flirty and Over text close on an actual invitation instead of another question.
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The questions
Each question, and why to ask it
Openers
What are you up to this weekend?
Why ask it
Small talk on the surface and reconnaissance underneath: you learn their schedule, who they spend time with, and whether they leave an opening for you. If they answer and then ask what you are doing, that is the opening.
What do you like to do for fun?
Why ask it
The plain version, and plain is fine when you have barely spoken. If the answer is 'not much, really', ask what they did last Saturday, which is the same question with a date on it. Keep hold of one thing they name, because it is your way in next time.
What kind of music are you into?
Why ask it
Nearly everyone has an answer, and 'a bit of everything' only means you ask for the last song they played. Get one recommendation, listen to it that night and tell them what you thought. That is a second conversation for the cost of three minutes.
What are you watching at the moment?
Why ask it
A show in progress gives you something to ask about every week. If you watch it too, you can argue about it. If you don't, ask whether it is worth starting and let them sell it to you without spoilers.
What are you into that you could talk about for an hour?
Why ask it
Better than asking about hobbies, because it gives permission to be enthusiastic about something small or unfashionable. Then let them have the hour rather than steering back to yourself.
How's your day going so far?
Why ask it
The most ordinary question there is, which is why nobody thinks twice about being asked it. The second question is what makes it work: when they say 'fine' or 'long', ask what made it long. Plenty of people are glad that someone did.
What do you do when you're not here?
Why ask it
For someone you only know from one place: a class, a job, a gym, a bus stop. It asks about the rest of their life without the stiffness of 'what are your hobbies', and whatever they name first is usually what matters most.
Can you settle an argument for me?
Why ask it
People like being asked to judge. Have a real and trivial dispute ready, such as whether cereal counts as dinner, and take the ruling seriously. If they ask who you were arguing with, you are now in a conversation.
How did that thing go, the one you were dreading?
Why ask it
Only works if you remember the test, the game, the shift or the interview they mentioned. It is the strongest opener on the page, because it proves you were listening last time.
I keep seeing you around. What's your name?
Why ask it
If the two of you have never actually spoken, this is the whole first move, and it is less dramatic than it feels. Say your own name first, then use theirs once before you leave so it sticks.
Is anyone sitting here?
Why ask it
The smallest possible first move, for a classroom, a cafeteria or a bus. If the seat is free, sit down and let a minute pass before you say anything else, so it does not feel like an ambush. If it is saved, say 'no problem' and try another day.
What did I miss?
Why ask it
For the day after you were out, or the ten minutes you were late. It makes them the one who knows, and their version, who got told off and what the teacher or manager actually wanted, is usually better than the real thing. Say thanks, and that you owe them one.
What did you think of that, honestly?
Why ask it
For the thing you both just sat through: a class, a meeting, a film, a game. A shared hour is the easiest common ground two people have, and 'honestly' invites the real review instead of 'yeah, it was fine'.
Have you started on that yet, or are we both pretending it isn't due?
Why ask it
For someone in your class or on your team. Shared dread is quick common ground, and it leads naturally to comparing notes or working on it in the same room.
What's good here? I always end up getting the same thing.
Why ask it
For a line, a cafeteria or a coffee counter. A recommendation is a tiny favor that people enjoy doing. Order what they suggest and report back, and you have a reason to talk next time.
I like that. Where did you get it?
Why ask it
A compliment on something they chose, a jacket, a bag, a sticker on a laptop, is easier to take than one about how they look. It usually comes with a story about a trip, a thrift store or a sibling's closet.
How do you know everyone here?
Why ask it
At a party or a friend's get-together it is the one question nobody finds strange. The answer hands you a mutual friend, a team or a class, and any of those is your next question.
Are you going to that thing on Friday?
Why ask it
For a game, a party, a school event or work drinks that you both already know about. A yes lets you say 'see you there', which is a plan without the weight of an invitation. If it is a no, ask what they are doing instead.
How was your weekend, and what was the best hour of it?
Why ask it
The Monday version of asking about their plans. 'The best hour' is what stops the answer being 'fine, yours?', and it makes them pick one thing, which comes out as a story.
What's the best meal you've had this month, and where do I get one?
Why ask it
Food is about the safest subject there is, and nearly everyone has a recent answer. A place they recommend is one sentence away from 'we should go', so remember the name.
What are you doing after this?
Why ask it
Asked as a class, a shift or a practice ends, it tells you whether there is room to walk out together. 'Nothing much' is an opening. A list of errands delivered while packing up is not, so say 'see you tomorrow' and mean it.
Getting to know them
Do you have any brothers or sisters?
Why ask it
An easy fact that leads somewhere: the oldest, the youngest, the one in the middle, an only child. Ask what the sibling is like, or what being the only one was like. If the answer is short or the subject changes, home may be complicated, so go with them to the new subject.
Do you have any pets, and are you a dog person or a cat person?
Why ask it
Someone with a pet will have a photo out within a minute, and asking to see another is always welcome. Someone without one tends to hold a firm view on dogs against cats anyway. Learn the animal's name, because asking after it later is a detail that gets noticed.
Are you a morning person or a night owl?
Why ask it
Small, but practical. It tells you when a message will find them awake and cheerful and when it will find them barely human. If the two of you are opposites, work out the hours when you are both up, and save the good conversations for those.
What's your favorite food?
Why ask it
If they say they like everything, ask what they would choose for a birthday dinner, which forces one answer. Get the details, down to who makes it or where it comes from. 'I know where to get a good one' is an easy thing to say a few weeks from now.
What would your dream job be?
Why ask it
Let the answer be unrealistic, because the fun is in the reason. Someone who says travel writer may mostly mean anywhere but a desk. Ask which part of the day in that job they are picturing, and do not bring up what it pays.
How would your friends describe you in three words?
Why ask it
Easier than describing yourself, since the friends take the blame. Notice which word they hesitate over or laugh at, and ask for the story behind that one. Then offer the three you would have guessed, provided all three are kind.
If I looked at your most played songs, what would surprise me?
Why ask it
Gets past the tidy answer people give when asked what music they like. The surprise is usually a musical, a parent's favorite band or something from a kids' film, and offering yours first makes theirs easier to admit.
What's the first thing you do when you get home?
Why ask it
The answer is unglamorous and therefore true: shoes off, snack, dog, straight to their room. It gives you a picture of their ordinary day, which is the part of someone's life you would actually be joining.
How did you end up doing what you do, whether that's a job, a course or a sport?
Why ask it
Asks for a story instead of a title, which works even if the job or the subject is dull. If it turns out a parent signed them up, or it was the only shift going, ask what has kept them at it.
Are you more of a plans person or a see-what-happens person?
Why ask it
Useful before you ask them anywhere. A plans person wants a day, a time and a place. A see-what-happens person would rather get 'are you around?' on the afternoon itself. If you are the opposite kind, say so and laugh about it now.
When's your birthday, and are you a big-fuss person or a please-don't-sing person?
Why ask it
Put the date in your phone before you forget it. The preference tells you what to do when the day comes round: a message at midnight and a fuss in front of everyone, or a quiet 'happy birthday' when nobody else is listening.
Who are your people: one big group, or a few separate friends?
Why ask it
Tells you how they socialize and what an invitation from them will look like, a crowd or one best friend. People with separate friends often like one-to-one time, which is useful to know before you suggest a group thing.
What's your best friend like, and how are you two different?
Why ask it
A best friend is easier to describe than yourself, so the first half comes quickly. The second half is where they describe themselves without noticing: 'she's the loud one' tells you who they think they are.
What are you a little bit competitive about?
Why ask it
Board games, grades, parallel parking, who gets to the door first. Whatever they name is something you can challenge them to, and a rematch is an easy reason to see each other again.
If someone handed you a ticket and a free week, where are you going?
Why ask it
An instant answer means they have been daydreaming about it, so ask what they would do on the first morning. If they would rather stay home, that is a real answer too, and worth knowing.
What's on your bucket list?
Why ask it
One item is enough, so do not ask for the whole list. Some are big, a country or a concert, and some turn out to be small and close to home, like a ride at the fair they have never been brave enough for. The small ones are worth remembering, because two people can do them on a Saturday.
What's something you've never tried that everyone else seems to have done?
Why ask it
Never been on a plane, never seen a famous film, never eaten sushi. Be amazed, not mocking, and note it: 'we should fix that' is one of the easier invitations to make.
What's the best present you've ever been given?
Why ask it
Listen to why it was the best: because it was useful, because it was a surprise, or because someone had clearly been paying attention. That reason tells you what kind of gesture lands with them.
What's a small thing that reliably makes your day better?
Why ask it
Expect something cheap and specific, such as the first coffee, the dog at the door or a song on the bus. Small things are the ones you can remember and bring up later, or one day simply show up with.
What are you looking forward to this month?
Why ask it
A concert, a trip, a game, the last day of exams. It gives you a date, and a date gives you two easy messages: 'have fun' beforehand and 'how was it?' afterwards. If they say 'nothing, really', ask what they would add to the calendar if they could.
What do your summers usually look like?
Why ask it
A job, a relative's house in another town, a camp, a lot of doing nothing. If a school year or a season is how you see each other, it also tells you whether they will be around when it ends, which is better learned before the last week.
What would you learn if grades and money didn't count?
Why ask it
Removes the sensible answer. What is left, pottery, a language, how engines work, is often something they have never told a teacher or a parent. If it is something that takes two people, a language or a card game, you have a reason to volunteer.
After a long week, do you want people around or a door that closes?
Why ask it
If they need the door, a quiet Friday is not about you, and an invitation for Saturday afternoon will land better than one for Friday night. If they want people around, Friday is the night to ask about.
What are you better at now than you were a year ago?
Why ask it
A year is short enough that they remember being bad at it: driving, cooking, a serve, saying no. Ask what made the difference, whether it was a person, a lot of practice or simply having no choice.
What's your favorite memory from when you were a kid?
Why ask it
Usually a place and a person: a grandparent's kitchen, a lake, the back seat on a long drive. Let them tell it slowly and ask for one detail, such as who else was there. You are being shown what happy looked like to them, so do not rush in with your own.
What were you like as a little kid, according to the people who were there?
Why ask it
Family verdicts arrive with stories attached: never stopped talking, hid behind a parent's legs, ran the playground. Ask whether it is still true. Most people think about it and then admit that it is.
What did you get in trouble for most as a kid?
Why ask it
Talking, daydreaming, arguing with the referee. It is usually the same trait they are known for now, with better manners, so the answer is a quick sketch of their character that they can laugh about.
What did you want to be when you were ten, and what happened to that?
Why ask it
Astronaut, vet, professional footballer. What happened to it matters more than what it was: some people dropped it with a shrug and some are still heading that way by a longer road, and you will hear which.
Which teacher, coach or boss do you still think about, and why them?
Why ask it
They might pick someone who believed in them or someone who was unfair. If it is the one who believed in them, ask what that person said. If it is the unfair one, let them be annoyed about it all over again.
Do you like living here, or are you planning your escape?
Why ask it
One person has a city picked out and a year to leave by, and another wants to stay ten minutes from their grandmother. It works whether they have lived here all their life or arrived last year. If they are going once school or a contract ends, now is a better time to hear it than later.
What's it like at your house on a normal weeknight?
Why ask it
Loud with siblings, quiet with a parent on a late shift, everyone behind their own door. It asks about home without asking who is in the family, and it explains why they can or cannot answer messages after dinner. If they keep it short, leave it.
Who in your family are you most like?
Why ask it
Listen for the trait that comes attached: 'my mom, we both have to be right' or 'my grandfather, he never sat still either'. Ask whether that relative would agree. Skip this one if they have already gone quiet about home.
Funny
What's your most embarrassing moment that you can laugh about now?
Why ask it
'That you can laugh about now' is what makes it safe, because they choose a story that has stopped stinging. Go first if they hesitate, with one of yours that is properly bad. Whatever they tell you stays with you: repeat it to friends and you will not be told another.
What's your biggest pet peeve?
Why ask it
Loud chewing, slow walkers, people who say 'no offense' and then offend. A complaint made with real feeling is funny, and it doubles as a list of things not to do around them. If you are guilty of the one they name, confess at once. It is better than being caught.
What's your guilty pleasure?
Why ask it
A reality show, a boy band, a snack that should not exist. The right reply is 'me too' or 'show me', never 'really?'. People only admit to the unfashionable things they love when they expect not to be judged, so prove them right.
If you could have one superpower, which would you pick?
Why ask it
An old question that still works, because the reason is the real answer. Someone who wants to be invisible and someone who wants to fly are after different things. Ask what they would do with it on day one, then explain why your choice is obviously better.
What's the first thing you'd buy if you won the lottery?
Why ask it
The first purchase is more telling than the grand plan: a house for a parent, a ridiculous car, never setting an alarm again. Then ask what they would keep exactly as it is. That half tells you what they already like about their life.
What's the dumbest way you've ever hurt yourself?
Why ask it
Everyone has a story that begins with being sure it would be fine. Laugh with them, ask whether there is a scar, and have your own ready, because they will ask.
What song lyric did you sing wrong for years?
Why ask it
A confession with no cost, and they will probably sing it to prove the point. If they can't think of one, offer yours. The wrong version usually makes more sense than the real one.
What was your username when you were eleven?
Why ask it
An early email address or gamer tag is a time capsule of whatever they loved that year, usually with a number on the end. Trade yours, and expect to be called by it for a week.
What were you scared of as a kid for no good reason?
Why ask it
The bathtub drain, escalators, one particular puppet. It is a sweet kind of embarrassing, and it lets them tell a story about being small without anything heavy in it.
Which animal do you think you could beat in a fight, and which one are you kidding yourself about?
Why ask it
People hold alarmingly firm views about geese. It is an argument with no stakes, so push back a little and see whether they double down or fold laughing.
What's the worst film you've ever sat all the way through, and why didn't you leave?
Why ask it
A bad film is more fun to describe than a good one. The second half is the real question: too polite, too stubborn, or there with someone they did not want to disappoint.
What's the worst thing you've ever tried to cook?
Why ask it
A kitchen disaster has a beginning, a smoke alarm and an end. If they claim they can cook now, ask what the first attempt at that dish was like. If they can't, a joint attempt at something simple is a plan that excuses you both in advance.
What's a harmless lie you tell all the time?
Why ask it
'On my way', 'I've seen it', 'no, I was awake'. Everyone has one, and admitting it is a small act of trust. You also learn what 'five minutes away' means when it comes from them.
What's the most trouble you've been in for laughing at the wrong moment?
Why ask it
An assembly, a serious meeting, a relative's speech. The story nearly always has a second person in it, the friend who caught their eye and set them off, so ask who it was and whether they still sit together.
If you opened a shop that sold only one thing, what would it sell?
Why ask it
Finds an obsession without asking for one: only socks, only grilled cheese, only pens that actually work. Ask what the shop would be called and whether you would get a discount.
What would your walk-in music be if a song played every time you entered a room?
Why ask it
The joke answers say as much as the serious ones: a boxing anthem, a cartoon theme, something slow and ominous. Pick one for them afterwards. They will be flattered or offended, and both are fun.
What's the most useless fact you know by heart?
Why ask it
Most people are carrying one around and waiting for a chance to use it. Trade facts until one of you runs out, and bring a new one the next time you see them.
Which Olympic sport would you be worst at, and how badly would it go?
Why ask it
Self-mockery by invitation, and the detail is the fun part: where on the pommel horse it goes wrong, how far the javelin fails to travel. Offer to be their coach, then describe your own event going worse.
What's an achievement from when you were little that you still bring up?
Why ask it
A swim meet ribbon, a spelling bee, a goal scored at age eight. They are allowed to brag because the stakes expired years ago, so be impressed and ask whether the certificate still exists.
What rule at school or work do you break every single day?
Why ask it
The answers are small: phone in a pocket, the back stairs, lunch at the desk. It shows you which rules they think are silly, and whether they break them openly or quietly.
What would your best category be on a quiz show, and which one would sink you?
Why ask it
The first half lets them claim expertise in something odd, and the second lets them confess a gap. If your best category is their worst, you have just become a quiz team.
Would you rather know what every dog thinks of you or what every baby does?
Why ask it
Dogs are the safe choice, since they like nearly everybody, and a baby will stare at anyone as if unconvinced. Whichever they pick, offer your guess at the verdict. It is a compliment you get to deliver in a dog's voice.
What's the longest-running joke you have with anyone?
Why ask it
It will not be funny to you, and that is fine: what you are hearing is how they keep a friendship going. If one silly thing has already come up between you twice, you are allowed to make it yours.
Flirty
What's your idea of a perfect date?
Why ask it
The best-known question on any page like this, and there is a practical reason to ask it: one person describes a restaurant and another describes a walk and a bag of fries. Listen for how much planning is in it and how many other people. Do not announce that you could arrange exactly that. Just remember it.
What's the first thing you notice about a person?
Why ask it
Their laugh, their shoes, how they talk to people they have no need to impress. It tells you what they pay attention to, which is more use than a list of requirements. If they turn it around and ask what you noticed about them, have a true answer ready.
What's your love language?
Why ask it
Shorthand for how someone shows they care and how they notice it in return: kind words, time together, small gifts, doing something helpful, or a hug. If they have not heard the phrase, ask how they can tell when someone likes them. The answer tells you which of your efforts would even register.
Do you believe in love at first sight?
Why ask it
Half the fun is the argument, so take the other side for a minute if they seem to be enjoying it. A yes usually arrives with a story about someone they know. A no tends to mean they think it takes time, which is good news for anyone who has sat two seats away all year.
What's your zodiac sign, and do you believe any of it?
Why ask it
You get the month they were born in, plus a view on whether the stars are in charge. A believer will want your sign so they can check the two of you, which is flirting with a chart. If they think it is nonsense, read them their horoscope anyway and ask how wrong it is.
Who was your first celebrity crush, and does it still hold up?
Why ask it
The safest way to bring up crushes at all, because the one in question was a poster on a wall. The choice at nine is usually funny, and 'does it still hold up' tells you a little about what they like now.
Do you have a type, or does it surprise you every time?
Why ask it
Listen for whether the list is about character, funny, calm, kind, or about looks. Do not measure yourself against it out loud. People who say they are always surprised are telling you the list was never the point.
What's the most attractive thing someone can do that has nothing to do with how they look?
Why ask it
Answers run to things like being good with animals, being kind to a waiter, or being very good at one particular thing. Take it as a description of what they notice, not as a script to act out next week.
What's a dealbreaker for you, however much you like someone?
Why ask it
Rudeness to strangers, never asking a question back, being glued to a phone. People answer this from experience, so there is often a short story behind it that they may not want to tell. Listen instead of defending yourself, even if one of them sounds a little familiar.
What's the nicest compliment anyone has given you?
Why ask it
They get to repeat something flattering about themselves without being the one who said it. Notice what it was about: their work, their sense of humor, how they treat people. A compliment from you will be believed in the same area, as long as it is one you mean.
Is being called cute a compliment or an insult to you?
Why ask it
Playful, and it slips the word into the conversation without quite aiming it at them. Some people hear 'cute' as 'harmless' and bristle. Either way you now know which word to use when you do mean it.
What's the cheesiest romantic thing you secretly like?
Why ask it
Flowers, a handwritten note, being walked home, a song sent with no explanation. 'Secretly' lets them admit it without sounding sappy, and the answer is about as clear a hint as you will ever be handed.
Would you rather get a handwritten note or a playlist made for you?
Why ask it
Both take effort, and people are quick to say which kind reaches them. If the two of you get closer, make the one they picked. Just not in the same week you asked, or it looks like homework.
Do you fall for people quickly, or does it creep up on you?
Why ask it
Worth knowing for the sake of your own patience. With someone who says it creeps up on them, a slow start is not a no: they need time and plenty of ordinary conversations before anything shows.
Have you ever been in love?
Why ask it
A bigger question than the ones around it, so save it for a quiet conversation that is already going well. 'I thought so at the time' is a complete answer. Do not ask who it was or how it ended, and if they ask you back, be as honest as they were.
Do you think you can tell when someone likes you?
Why ask it
A lot of people will tell you they are hopeless at it. That is your opening to ask what someone would have to do for them to notice, and whatever they say next is close to a set of instructions.
Have you ever liked someone and never told them?
Why ask it
Plenty of people have, and the story is safe to tell because it is over. It also puts the idea of telling someone on the table. Do not ask who it was, and never guess.
Would you want to know if someone liked you, even if you didn't feel the same way?
Why ask it
A yes means honesty would be welcome whatever the answer turned out to be. A no means they find that moment uncomfortable, so go slower and let a few easy conversations do the work first.
What's the best way anyone has ever let you know they liked you?
Why ask it
You hear what worked on them, told as a story instead of a rule. Pay attention to whether it was words, a gesture or simply showing up a lot. Leave alone the matter of what happened with that person.
Would you rather be asked out face to face, or by message where you get a minute to think?
Why ask it
Directly useful, and asking commits you to nothing. People who want the minute are not being cold. They just dislike answering in front of an audience, even an audience of one.
Where would you take someone if you wanted them to like you?
Why ask it
Shows what they think is impressive about their own world: a view, a food stall, a record shop, their dog. If they describe it with real enthusiasm, the natural reply is that you would like to see it.
If we got paired up for a project, would we get it done or just talk?
Why ask it
A way of saying you like talking to them, with a joke as cover. 'Just talk' is the answer you are hoping for, though 'we would get it done' can come with a grin too. Either way you have more or less agreed to be partners the next time one is assigned.
Which of us would last longer without a phone, and how long before you cracked?
Why ask it
A small competition with the two of you as the only entrants, which is most of what flirting is. If they insist they would win, propose a real test, loser buys the snacks.
Is it just me, or do we keep ending up next to each other?
Why ask it
Names the pattern out loud, including the part where you may have arranged it. 'I noticed' with a smile is a good sign. A blank look means it really was just you, so laugh, blame the seating plan and carry on.
What did you think of me when we first met?
Why ask it
Safer than asking what they think of you now, because it is about the past and can be told as a joke. 'I thought you were scary' and 'I thought you hated me' are both good news, since either way they noticed you. Give your first impression of them in return, and make it a kind one.
Am I easier or harder to talk to than you expected?
Why ask it
It is fishing and it admits as much, which is what keeps it charming instead of needy. Ask only when the conversation is already easy, and if the answer is 'harder', laugh and ask what they had expected.
Can I tell you something I've noticed about you?
Why ask it
Asking first turns a compliment into something they have agreed to hear. Have a specific one ready about something they did, how they stuck up for a friend or how they explain things, and then let it sit without adding a joke.
Do you have a crush on anyone right now?
Why ask it
Most people who ask this are hoping to hear their own name, and the other person usually knows it. Ask lightly, and only when it is just the two of you. 'Maybe, why do you ask?' with a smile is encouraging. Do not press for a name or guess at one, and if they name someone else, be as kind about it as you would want them to be.
Are you seeing anyone at the moment?
Why ask it
The question most of this page circles. Ask it plainly, once, after a conversation that has gone well, and believe the answer. If it is yes, be gracious, stay friendly, and leave the rest of this group alone.
Is there something you've been wanting to do that I could come along to?
Why ask it
Ends the conversation with a plan instead of another question, and it is easier to say yes to than a direct invitation. A vague answer here is usually a polite no, and worth accepting as one.
Do you want to get food sometime, just the two of us?
Why ask it
'Just the two of us' removes the doubt that makes group hangouts so hard to read. A clear ask gets a clear answer. 'Maybe, I'm pretty busy' with no other day offered is a no, and taking it well keeps the friendship.
Over text
What are you up to right now?
Why ask it
The standard first text, and fine as long as you have somewhere to take it. Before you send it, know what you will say to 'nothing, you?': a photo of what you are doing, or something specific you wanted their opinion on. Sent three days running with nothing behind it, it starts to read as boredom.
Did you catch what we're supposed to do for tomorrow?
Why ask it
The practical excuse is the oldest first text there is, and it works because it is easy to answer. They may well see through it, which is fine. Once they reply, add one line that has nothing to do with homework or the schedule.
Did you get home okay?
Why ask it
A real question with a kind reason behind it, for a night when you were both at the same thing. The reply usually opens a recap of the evening, which is a better conversation than anything you could have planned.
Saw this and thought of you. Was I right?
Why ask it
It needs something attached: a photo, a song, a joke about the thing they told you last week. It shows you remembered a detail. If it gets a one-word reply, don't follow it with another the same day.
I need a second opinion: which of these two?
Why ask it
Send two photos, of shoes, haircuts or pizzas. A small decision takes five seconds to answer, which suits someone who is busy, and they will want to know afterwards whether you took their advice.
What was the high and the low of today?
Why ask it
A two-part question can't be answered with 'fine'. The low gives you something to check on tomorrow, and checking is what turns a string of messages into knowing someone.
Has anything happened today that you've been dying to tell someone?
Why ask it
It makes you the someone. On a slow day the answer is 'no, you?', so have a small story of your own ready before you send it.
Quick round: sweet or salty, early or late, call or text?
Why ask it
Either-or questions suit a phone, because each answer is one word and people usually send three back. Three in one message is the limit, and the answer worth following up is the one they explain without being asked.
Want to play 21 questions? You go first.
Why ask it
The game is an excuse to ask things you would not ask cold, and both of you know that. Take turns, answer every one you ask, and allow each other a pass. Start silly. A direct question lands better at number fifteen than at number two.
Am I distracting you from something, and should I keep going?
Why ask it
It teases, and it also checks whether now is a good time. 'Yes, please keep going' is about as warm as a text gets. If they really are busy, say good luck and go, which they will remember kindly.
Why are you still awake?
Why ask it
For when you both turn out to be online late. People type things at midnight that they would not say at lunch, so be kind with whatever comes back. Do not make a habit of keeping them up, and be the one who says goodnight first now and then.
What's your screen time today, and which app is to blame?
Why ask it
A number they can look up in ten seconds, followed by a confession. Send yours as well. The app they blame tells you what they do with a spare hour, and gives you something to tease them about gently.
I need a name for something: a plant, a playlist, a pet rock. What have you got?
Why ask it
Gives them a small creative job with no wrong answer. Use the name they pick. The plant or playlist becomes a running reference, and you can send updates on it for weeks.
What's the most on-brand thing you've done this week?
Why ask it
They have to know what their own brand is, so what comes back is a small confession: lost a water bottle again, corrected a teacher, cried at a commercial. Agree with it only if it is flattering.
Want to guess each other's usual order: coffee, pizza, anything?
Why ask it
A guessing game that shows how much attention each of you has been paying. Being wrong is fine, and being right is a compliment. Either way you finish knowing an order you might need one day.
Are you more yourself over text or in person?
Why ask it
Some people are funnier typed and shyer out loud, and they usually know it. If they say text, do not read too much into a quiet hello in the hallway. If they say in person, stop typing and go and find them.
What time are you done today? I want to hear how it went.
Why ask it
For the day of their exam, game, audition or interview. It is a good-luck message with a follow-up built in, and it leaves the timing to them. Then actually ask, at the time they gave.
Do you like it when someone texts first, or would you rather start it?
Why ask it
Settles who goes first without making it about the two of you. If you have started the last five conversations and they say they like starting, take a few days off and see whether they do.
Want to start the same show tonight and message through it?
Why ask it
A plan that needs no ride and no money. One episode a night gives you a week of things to say, and by the finale, watching the last one in the same room is an easy thing to suggest.
Are you free on Saturday afternoon? There's something I think you'd like.
Why ask it
A day, a time and a reason give them something specific to say yes to, where 'we should hang out sometime' gives them nothing. Have the something ready to name. If the answer is no and no other day is offered, leave it there.
Deep
What are you most proud of so far?
Why ask it
'So far' stops it sounding like a job interview. It might be a grade, a team, getting through a hard year or teaching a younger brother to ride a bike. Ask what it took. It is a rare chance to say this out loud without being accused of bragging, so let them enjoy it.
Where do you want to be in five years?
Why ask it
Not a test of ambition. 'No idea' is honest and common, so follow it by asking what they hope has changed by then. If they have a city, a course or a job picked out, ask what drew them to it. Keep yourself out of the picture they describe, because it is too early for that.
Who do you look up to?
Why ask it
It could be a relative, a coach, an older friend or someone they have never met. Ask what that person does that they wish they could do. The qualities they list are the ones they are working on in themselves, which tells you more than a list of favorite things.
How are you different once someone has known you for more than a week?
Why ask it
You are asking how they think they come across at first, which is often at odds with the impression you have. 'Louder than I seem' and 'less confident than I look' are common answers, and both tell you how to treat them now.
What's a time you were completely wrong about someone?
Why ask it
A story about a first impression that got revised, usually ending in a friendship. It shows they can update their view of a person, which matters to anyone hoping to be seen differently one day.
Who do you call first when something good happens?
Why ask it
The name they give is the person closest to them, whether that is a parent, a sibling or one particular friend. A long pause sometimes means there is nobody, so do not push. Tell them who yours is and move on.
Where do you go when you need to think?
Why ask it
A long drive, the shower, a bench behind the gym, the walk home with headphones in. You learn how they sort things out, and that a day of silence from them may only mean they have gone there.
What do you think about when you can't sleep?
Why ask it
Usually it is whatever is unfinished: a test, an argument, something they said three years ago that nobody else remembers. If it is a worry, you do not have to fix it. If it is an elaborate plan for a treehouse, ask for the full design.
When do you feel most like yourself?
Why ask it
The answer is a place, an activity or a set of people. Compare it with where you normally see them. If you only know them at school or work and they are most themselves on a field or in a kitchen, you have not really met them yet.
What do you hope people say about you when you're not in the room?
Why ask it
This gets at what they most want to be true about themselves: funny, reliable, kind, good at what they do. If you have seen that quality in them, say so with an example, which lands far better than a general compliment.
What's the nicest thing someone's done for you that they've probably forgotten?
Why ask it
A lift at short notice, a saved seat, a friend who noticed they had gone quiet. What they remember is what counts as kindness to them, and small things of the same sort are the ones they would notice from you.
What's something a parent or grandparent says that has stuck in your head?
Why ask it
Family sayings get quoted with an eye-roll or with affection, and you can hear which. It is a gentle way into how they were raised. Leave it there if home sounds like a sore subject.
How does someone earn your trust, and how do they lose it?
Why ask it
The losing half usually comes with a story about a secret that got passed on. Whatever they describe, treat it as the rules for you. The first one is that nothing they tell you reaches your group chat.
What matters most to you in a relationship?
Why ask it
Asked this broadly, it can be answered about friends, family or dating, and they choose which. Honesty, being given room, someone who laughs easily: whatever comes first is often what was missing somewhere before. Do not answer with a promise. Say what yours is and leave the two side by side.
What's been harder than it looks this year?
Why ask it
They can answer at any depth: a class, a friendship, something at home. Take what is offered and do not dig for more. 'That sounds hard' is a complete reply.
What are you hard on yourself about?
Why ask it
The people who seem most sure of themselves often have the longest answer. Do not argue them out of it. Say what you see from the outside, once, and let them decide whether to believe you.
What did you believe about yourself that turned out not to be true?
Why ask it
'I'm bad at math', 'I'm shy', 'I'm not athletic'. It is a hopeful question, because the answer is a story about finding out they were wrong, and it shows you who they are turning into.
What scares you that isn't spiders or heights?
Why ask it
Ruling out the easy answers gets you the real ones: letting people down, being left out, staying the same. Offer one of your own, keep it brief, and never bring theirs up later as a joke.
Do you think things happen for a reason, or do we make the reasons up afterwards?
Why ask it
One for a long walk or a late conversation, and there is no right side. Ask for an example from their own life. The example is more interesting than the opinion, and harder to argue with.
What do you hope is different by this time next year?
Why ask it
Hopes at this range tend to be close to home: making a team, finishing a course, a friendship mended, a room of their own. Resist drawing up a plan for them. If they are leaving for a new school, a new city or a new job, this is also where you find out.
What's something you want that you haven't told many people about?
Why ask it
It might be a place, a career or a kind of life. Being told is a compliment, so do not rule on whether it is realistic. Ask what the first step would be, and remember to ask about it again in a month.
What's something you'd want someone to know about you early on?
Why ask it
Hands them control of what gets said next, so it can be a boundary, a commitment, or something they are usually nervous to mention. Whatever it is, take it at face value rather than reassuring it away.
What should I ask you about the next time we run out of things to say?
Why ask it
A last question that assumes there will be a next time, which is a small flirtation in itself. Whatever they name, a band, a sister, a half-built project, is what they wanted to talk about and did not get to. Open with it when you next see them.
How to use these questions
Practical guidance for the conversation itself
Pacing and picking
Two or three in a whole conversation
These work as prompts, not as a list. One good question, followed by ten minutes of actual conversation about the answer, does more than six questions in a row.
Pick the group for the moment
Openers are for someone you have barely spoken to, and several only work in a particular spot: an empty seat, a line, a party, the end of a class. Getting to know them and Funny suit the stage where talking is already easy. Flirty is for when they have started asking you things back, and the Deep questions are for later, in person, when nobody is in a hurry.
Follow the answer, not the list
If they mention a sister, a bad manager, or a trip, the next question is about that. Returning to a prepared question after an interesting answer is the thing that makes a conversation feel like an interview.
Asking over text
Which groups travel by message
The Over text group was written for a phone, and most of Openers and Funny works there too. Keep Deep for when you are face to face. Anything about stress, trust, or what they are hard on themselves about needs tone of voice and a pause, neither of which a phone provides.
One question per message
A message with three separate questions gets an answer to the easiest one. Send one, reply properly to what comes back, and only then ask the next. Reacting to their answer matters more than having another question ready.
Let a slow reply be slow
People are in class, at work, at practice or asleep, and a reply that takes four hours is not a verdict. A second message asking whether they saw the first helps nothing. If two of yours in a row go unanswered, stop and let them come to you.
Use the phone to get off the phone
Texting is good at keeping things warm between the times you see each other and bad at replacing them. Once the messages have been easy for a week or two, the Saturday question at the end of Over text is there to turn them into a plan.
Keeping it two-sided
Answer everything you ask
Volunteer your own answer without being asked, and go slightly first on anything personal. Asking someone to be open while staying vague yourself reads as either evasive or as an assessment.
Match their depth rather than exceeding it
If they give short answers, stay light and try again another day. Pushing into vulnerability that has not been reciprocated is how early interest turns into discomfort.
Notice whether they ask anything back
Whether they ask you anything back is the thing to watch in an early conversation. Someone who answers well but never asks is being polite, which is useful information to have sooner rather than later.
What to avoid
Their exes and their last relationship
It is tempting because it feels like information, but early on it comes across as either jealous or as comparison shopping. Wait until they raise it.
Questions that are really tests
Do you like me, what do you think of me, would you ever go out with someone like me: asked early, these put a person on the spot and produce a performance rather than an answer. The Flirty group asks how they like to be approached and what they notice in people, and keeps its direct questions for the end, after a conversation that has plainly gone well.
Flirting with an audience
A flirty question asked in front of their friends, or in a group chat, turns a private moment into a show, and most people protect themselves by laughing it off. Ask when it is just the two of you. If a playful question gets a flat answer or a change of subject, go back to Funny and leave it for another day.
Mistaking politeness for interest
People answer questions to be kind. Short replies, no questions back and a soft response to an invitation usually add up to a no, and reading them that way saves you both an awkward month.
Asking twice
One clear invitation is enough. If the answer was no, or a maybe with no other day offered, do not ask again next week and do not send a friend to ask for you. You will probably still share a class or a shift, and being friendly and ordinary afterwards is what keeps that comfortable for both of you.
Passing their messages around
A screenshot sent to your friends for advice tends to travel, and if it gets back to your crush the trust goes with it. If you need help with a reply, describe the message instead of forwarding it. Assume that anything you send can be shown around as well.