Quick summary
- 100 questions sorted by situation, from the first message to the first date.
- One question at a time: three in the same message reads like a form.
- Watch the follow-ups more than the answers, that's where real interest shows.
- Flirting works by suggesting, not announcing, and always leaving a way out.
- These questions are openings, not a script.
You know the moment. The conversation is going round in circles, the «good, you?» pile up, and you can feel that if nobody brings something else, it's going to die politely in a «have a good evening then». With a crush, every exchange counts double. So sooner or later we all end up staring at our phone with no idea what to send.
A good question does two things at once: it shows you're genuinely interested, and it makes them want to answer. That's all you ask of a conversation that's just starting. The 100 questions below are built for it.
They're sorted by situation, from the first message to the first date. We write «he» for simplicity, but everything obviously works in every direction.
By message, to open or reopen (1-15)
The short format, perfect to start a conversation or wake up a thread that's drifting off. Easy to send, easy to answer, and that's plenty to get things going!
- Your day in three emojis, no cheating?
- Are you more of a four-minute voice note or a wall of text?
- What are you listening to on repeat right now?
- Your current series, the one you hide and the one you own?
- If I say «best snack at 11pm», what do you answer?
- Last photo on your phone you can send me without shame?
- What's your completely useless talent?
- Last thing that made you laugh alone in the street?
- Which app would you delete from your life if you could?
- What's the best thing that happened to you this week?
- If you were paid to do one single thing, what would it be?
- Your most used emoji, shall I bet I can guess it?
- The song that puts you in a good mood in ten seconds?
- What's your perfect Sunday, hour by hour?
- What should I absolutely know about you before we keep talking?
To get to know him (16-35)
The fundamentals. This is where you find out who he really is, beyond the character of the first exchanges, and believe me, there are often surprises.
- What are you passionate about to the point of losing track of time?
- How would you describe yourself in three words, and which three would your friends pick?
- What's your best memory of the last five years?
- What did you want to be when you were 8?
- Are you close to your family, or is it complicated?
- The trip that marked you most, where was it and why that one?
- What do you do with a day entirely to yourself?
- Big group of friends or two very close people?
- What's the bravest thing you've ever done?
- What puts you in a bad mood every single time?
- Do you have a strange ritual nobody knows about?
- What's your favourite place in your city?
- The book or film that changed something in your head?
- What do you believe in: fate, chance, effort?
- What will you always defend, even against everyone?
- What are you proudest of, the one you don't talk about?
- What makes you feel alive?
- Would you rather be admired or understood?
- What do people gently laugh at you for?
- What would you do with your life if you were certain to succeed?
Funny, to make him laugh (36-50)
Humour is the shortest route between two people who like each other. These questions carry no stakes at all, and that's why they work so well.
- What's your favourite conspiracy theory, the one you half defend?
- Which animal would be your official spokesperson?
- How long would you survive in a horror film?
- If your life were a film, what genre, and who would play you?
- The worst present anyone has ever given you?
- Would you rather fight one giant duck or a hundred tiny ones?
- What's your most scandalous food take?
- The most memorable embarrassment of your life, the one that still makes you wince?
- Which completely rubbish superpower would you still accept?
- Your worst message sent to the wrong person?
- What's the most absurd lie you've told to get out of something?
- What name would you give a goldfish, without thinking?
- If animals could talk, which would be the most unbearable?
- What's your worst habit that you still find slightly brilliant?
- You get a million but must spend it in 24 hours with no investing: what do you do?
A bit more personal (51-65)
Bring these out when the conversation is well under way and you sense it can go further than jokes. That's often where a crush becomes something else...
- What genuinely makes you happy, not on paper, for real?
- Do you talk about your feelings easily, or keep everything in?
- What's the hardest lesson life has taught you?
- What are you afraid of, and it can't be spiders?
- What would you like people to understand about you without having to explain it?
- What made you the way you are, in one story?
- What don't you forgive easily?
- Have you ever changed your mind about something important? Tell me.
- What makes you feel safe with someone?
- What do you do when things are bad, your real reflex?
- Is there a dream you've never said out loud?
- Where do you see yourself in five years, without the ready-made answer?
- What would nobody ever guess just by looking at you?
- Which person has mattered most in your life so far?
- What would you repair, if you could?
To flirt, without overdoing it (66-80)
Flirting that works follows one simple rule: suggest rather than announce. These questions send the signal while leaving the other person free to take it... or not. That's what makes them effective without ever being heavy-handed.
- What did you notice first about me, honestly?
- What's your idea of a perfect date, with no unlimited budget?
- Do you believe in love at first sight, or in things that get built?
- What makes you fall for someone, the real answer?
- Are you more open first moves or subtle signals?
- What makes you curious about me, right now?
- If we spent an evening together, how would you imagine it?
- What do you remember about people: the eyes, the laugh, the voice?
- Do you prefer the beginning of a story or a settled one?
- Apparently everyone has a seduction technique. What's yours?
- If I suggested something improvised tomorrow, would you say yes?
- What would make an evening bad for you, so I know what to avoid?
- What do you think about nicknames? Purely theoretical question.
- Between us, do you always answer everyone this fast?
- If this conversation were the start of a film, what would it be called?
To see whether it could work between you (81-92)
Under their light conversational cover, these twelve questions check the essentials: your rhythms, your expectations, your outlooks. It's the work done by couple questions once a relationship is under way; in crush form, you check the same things without ever asking THE frontal question.
- What's your ideal weekend: tight plan or total improvisation?
- Do you need a lot of time to yourself, or do you like continuous presence?
- Are you more messages all day or meeting up in the evening?
- What would make you run at the start of a relationship?
- Would you say you're jealous, honest answer?
- What's your way of showing someone matters to you?
- Big conversations or silent closeness?
- What do you want from a relationship, ideally?
- Do you think you can tell each other everything, or should you keep private gardens?
- Your level of organisation on a scale from 1 to «I have a spreadsheet»?
- What reassures you about someone you're starting to like?
- If this became serious between us, what would absolutely have to stay as it is now?
In person, at the first date (93-100)
Eight questions to save for face to face. Open enough to get him talking, light enough never to weigh down the mood. Just what a first date evening needs.
- So, what's it like meeting me in person compared to the messages?
- What's the most surprising thing you've learned about me since we started talking?
- What do you do afterwards, if this evening goes too well?
- What do you tell your friends about me, the truth?
- What are we doing next time? Trick question: there is a next time.
- Are you more nervous or more at ease than you expected, right now?
- If you had to show me a place you love, where would it be?
- Right. Out of ten, this evening?
And if this date turns into a relationship, you'll see the register shift on its own: the questions you ask your boyfriend have little to do with the ones you asked your crush, and that's a very good sign.
And if you don't dare send anything at all?
A quick word for whoever has read this far without sending a single message: that's normal. A crush, by definition, makes you lose your nerve. Start with questions 1 to 15. Just one. The simplest, the one that sounds like you. The goal isn't to be brilliant, it's to open a door.
And if you already talk every day but still can't tell whether it's mutual, stop rereading your conversations for the tenth time. Honestly. There are far more reliable signals than your interpretation of his emojis at 1am.
| The stage | The right register | The classic mistake |
|---|---|---|
| The first messages | Light, short, one question at a time | The wall of text expecting an essay |
| Getting to know him | Curious, about concrete things | The disguised interrogation |
| Making him laugh | Absurd, never at his expense | The joke that tests the limits |
| Flirting | Suggested, with a way out | The compliment that makes him uncomfortable |
| The first date | Open, and genuinely listened to | Reciting your prepared questions |
And if what is really blocking you is knowing what you feel, you can sort a crush from real feelings in 35 questions.
Is he thinking about you, or just being polite?
A series of questions goes through the real signals, the ones you don't notice when you're in the middle of it: his follow-ups, his attentions, the way he is when you're there. Instant result, and nobody will know.
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Last piece of advice, the most important of all: these 100 questions are openings, not a script. The day you no longer need a list to talk for hours... you'll know you played it well.
Read also100 questions to ask your boyfriend, from light to the big conversations