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21 Questions to Ask Your Crush

Flirty questions to get closer to someone you like

The trick with a crush is momentum: start with easy favorites, move into "us" hypotheticals, and let the flirty ones land when the moment is right. This list runs in that order — or shuffle it in play mode and let fate pick.

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21 Questions
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Question #1

What was your first impression of me?

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All Questions

105 questions
#1
easy

What was your first impression of me?

Follow-ups: Did it change after we talked? • What do you think now?
#2
easy

What is the first thing you noticed about me?

Follow-ups: Do you still notice it? • What came after that?
#3
easy

What made you want to talk to me the first time?

Follow-ups: Was it planned or spontaneous? • Are you glad you did?
#4
easy

If you could plan a dream first date, what would it look like?

Follow-ups: Indoor or outdoor? • What would we wear?
#5
easy

What is your favorite way for someone to show they like you?

Follow-ups: Words or actions? • Has anyone done it well?
#6
easy

Do you believe in love at first sight?

Follow-ups: Why or why not? • Has it ever happened to you?
#7
medium

What is the most romantic thing someone could do for you?

Follow-ups: Big gesture or small? • Would you cry?
#8
easy

What song do you think about when you think of me?

Follow-ups: Why that one? • Would you share the playlist?
#9
medium

When did you realize you liked me?

Follow-ups: Was it a specific moment? • Did anyone else notice first?
#10
medium

What is something you were nervous to say to me?

Follow-ups: Why was it hard? • Are you glad you said it?
#11
easy

If we could go anywhere together tomorrow, where would you take me?

Follow-ups: What would we do there? • How long would we stay?
#12
easy

What is your favorite thing we have done together so far?

Follow-ups: What made it special? • Should we do it again?
#13
medium

What do we have in common that most people would not guess?

Follow-ups: How did you discover it? • What else is hiding?
#14
easy

What is one thing you want to learn about me?

Follow-ups: Why that? • Will you ask me right now?
#15
easy

What made you smile the last time we talked?

Follow-ups: Do I do that often? • What was the moment?
#16
easy

If you had to describe me in three words, what would they be?

Follow-ups: Which one is your favorite? • How would you describe yourself?
#17
easy

What compliment from me would make your whole week?

Follow-ups: Have I given it yet? • What would you say back?
#18
easy

What is your idea of the perfect goodnight text?

Follow-ups: Emoji or words? • Who texts first?
#19
medium

Do you prefer slow, steady romance or a whirlwind?

Follow-ups: Why? • Has your answer changed before?
#20
easy

What is your favorite time of day and why?

Follow-ups: What do you usually do then? • Could we share it?
#21
easy

What could you talk about for an hour with zero preparation?

Follow-ups: Where did that interest come from? • Would I like it too?
#22
easy

What is a small thing that instantly makes your day better?

Follow-ups: Did it happen today? • Can I do it for you?
#23
easy

What is your comfort food after a hard day?

Follow-ups: Can you make it yourself? • Should we get it sometime?
#24
easy

What is the last thing that made you laugh out loud?

Follow-ups: Who was there? • Would I find it funny too?
#25
easy

What is your favorite season for a date?

Follow-ups: What would the date be? • What do you love about that season?
#26
easy

What kind of music matches your mood lately?

Follow-ups: Any artist on repeat? • What would our shared song be?
#27
easy

What is a movie you could rewatch forever?

Follow-ups: What makes it rewatchable? • Would you make me watch it?
#28
easy

What is your favorite way to waste a Sunday?

Follow-ups: Alone or with people? • Could I join?
#29
easy

What is one food you refuse to eat?

Follow-ups: Why the strong feelings? • Could anyone change your mind?
#30
easy

What is the best meal you have ever had?

Follow-ups: Where was it? • Could we recreate it?
#31
easy

Coffee, tea, or something else — what is your usual order?

Follow-ups: How did you find it? • What would you order for me?
#32
easy

What is your favorite holiday tradition?

Follow-ups: When did it start? • Could we start one of our own?
#33
easy

What is a place in town you love showing people?

Follow-ups: What makes it special? • When are you taking me?
#34
easy

If we did karaoke together, what would our duet be?

Follow-ups: Who takes the high notes? • Are we good or gloriously bad?
#35
easy

What is your favorite board game or video game?

Follow-ups: Would you let me win? • Game night soon?
#36
easy

What concert is still on your bucket list?

Follow-ups: Why them? • Would you go with me?
#37
easy

What is a TV show you wish you could watch again for the first time?

Follow-ups: What makes it that good? • Would you rewatch it with me?
#38
easy

What is your favorite thing about your daily routine?

Follow-ups: What would you change? • Where would I fit in?
#39
easy

What is one app you could not live without?

Follow-ups: What do you use it for? • What is your screen time?
#40
easy

Are you more of a planner or a go-with-the-flow person?

Follow-ups: Does it work for you? • Which one am I?
#41
medium

What is a trait you have that surprises people?

Follow-ups: Why does it surprise them? • When do you show it?
#42
easy

What is something you are weirdly competitive about?

Follow-ups: Have you ever lost badly? • Should we compete sometime?
#43
easy

How do you like to celebrate small wins?

Follow-ups: What was your last win? • Can I celebrate the next one with you?
#44
easy

What is your biggest pet peeve?

Follow-ups: How do you handle it? • Have I done it yet?
#45
easy

What is something you are irrationally afraid of?

Follow-ups: Where did it come from? • Would I have to protect you?
#46
easy

Are you a morning person or a night owl?

Follow-ups: What is your best hour? • Could our schedules match?
#47
medium

What is a habit you secretly love even though it is bad for you?

Follow-ups: Will you ever quit? • Should I join you?
#48
medium

What is the most spontaneous thing you would do if I said yes to anything?

Follow-ups: Why have we not done it? • Is this you saying yes?
#49
easy

How do you recharge after a long week — alone or with people?

Follow-ups: What does that look like? • Would I be invited?
#50
easy

What is something everyone seems to love that you do not get?

Follow-ups: Have you tried it again? • What do I love that you do not get?
#51
easy

What is a skill you picked up surprisingly fast?

Follow-ups: How did you learn it? • Could you teach me?
#52
easy

What is a party trick you would show me if I dared you?

Follow-ups: How good is it really? • Consider yourself dared?
#53
easy

What is one thing that always calms you down?

Follow-ups: How did you find it? • Would it work on me?
#54
easy

What is your most-played song right now?

Follow-ups: What does it say about you? • Would it go on our playlist?
#55
medium

How would your best friend describe you in one sentence?

Follow-ups: Is it accurate? • How would I describe you?
#56
easy

What is something you take way too seriously?

Follow-ups: Why do you think that is? • Should I take it seriously too?
#57
medium

What is something you should take more seriously than you do?

Follow-ups: What is stopping you? • Could I help?
#58
medium

What is a small thing that makes you trust someone?

Follow-ups: Have I done it yet? • What breaks trust fast?
#59
easy

What is the best way to cheer you up?

Follow-ups: Who knows how to do it? • Should I take notes?
#60
medium

What does a healthy relationship look like to you?

Follow-ups: Who modeled it for you? • What is non-negotiable in it?
#61
easy

What is your love language — words, time, gifts, touch, or acts of service?

Follow-ups: How did you figure it out? • What do you think mine is?
#62
medium

What is a deal breaker you will never compromise on?

Follow-ups: Where did it come from? • Have you ever ignored one?
#63
easy

What is the best piece of relationship advice you have heard?

Follow-ups: Who gave it? • Do you follow it?
#64
easy

Do you think opposites attract, or do birds of a feather flock together?

Follow-ups: What is your evidence? • Which one are we?
#65
medium

What is one thing you want a partner to always remember about you?

Follow-ups: Why that thing? • Would I remember it?
#66
easy

Rainy day, both of us free — what is the move?

Follow-ups: Food involved? • Movie or adventure?
#67
easy

What is something a partner could do that would instantly impress you?

Follow-ups: Has anyone done it? • Is it achievable for me?
#68
easy

Do you prefer big romantic gestures or small daily ones?

Follow-ups: Why? • What is one example of each?
#69
medium

What is something you have never told a crush before?

Follow-ups: Why is now the time? • How do you feel saying it?
#70
easy

What is your favorite memory of us talking late at night?

Follow-ups: What made it special? • When is the next one?
#71
easy

What is something you think we would be great at together?

Follow-ups: How do you know? • When do we start?
#72
easy

If we wrote a song together, what would it be about?

Follow-ups: Who sings it? • Would it be a hit?
#73
easy

What is one thing you would love for me to teach you?

Follow-ups: Why me? • When is lesson one?
#74
medium

What is the most thoughtful gift you have ever given someone?

Follow-ups: What was their reaction? • What would you give me?
#75
easy

If we could teleport anywhere for one hour tonight, where would we go?

Follow-ups: What would we do there? • Would one hour be enough?
#76
easy

If we started a band, what would we call it?

Follow-ups: What genre are we? • Who is the lead singer?
#77
easy

You win a free trip for two — where are we going?

Follow-ups: Beach or mountains? • What is the first thing we do?
#78
easy

If our first date had to cost under ten dollars, what would we do?

Follow-ups: Would it still be fun? • What does that say about us?
#79
medium

If you could relive one day of your life, which would it be?

Follow-ups: Why that day? • Would you change anything?
#80
easy

If we were stuck in an elevator for three hours, how would we pass the time?

Follow-ups: Would you panic? • What would we learn about each other?
#81
easy

If you got to pick my phone wallpaper, what would you choose?

Follow-ups: Why that? • What is yours right now?
#82
easy

If we had to win a costume contest as a duo, what would we dress as?

Follow-ups: Who had the idea? • How committed are we to the bit?
#83
medium

If you could read my mind for one minute, when would you use it?

Follow-ups: What do you think you would find? • Should I be worried?
#84
easy

If we made a movie together, would it be a comedy or a romance?

Follow-ups: Who plays us? • What is the plot?
#85
easy

What would your ideal surprise from me look like?

Follow-ups: Any hints for next time? • Are you good at keeping secrets?
#86
easy

If we could only eat one cuisine together for a year, what would it be?

Follow-ups: What is your order? • What breaks first — you or me?
#87
easy

If we were characters in a show, who would we be?

Follow-ups: Which show? • Do we survive the season?
#88
easy

If you had one dare to give me right now, what would it be?

Follow-ups: Why that one? • Would you do it too?
#89
medium

If we switched phones for a day, what would surprise me most?

Follow-ups: What would surprise you? • Are you brave enough?
#90
easy

What is the best part of your week usually?

Follow-ups: Was this week typical? • Could I be part of it?
#91
easy

What is something you are looking forward to this month?

Follow-ups: Why is it exciting? • Can I come along?
#92
easy

What is a subject or topic you could study forever?

Follow-ups: What got you into it? • What would you do with it?
#93
easy

What job would you do just for the fun of it?

Follow-ups: Why is it fun? • Would you be good at it?
#94
easy

What is the weirdest job you have ever had or wanted?

Follow-ups: What happened? • Would you do it again?
#95
easy

What is one thing on your to-do list you keep avoiding?

Follow-ups: Why is it hard? • Do you need an accountability partner?
#96
easy

What is your favorite thing about where you live?

Follow-ups: What would you change? • Would I like it there?
#97
easy

What is a place near here you have never been but want to try?

Follow-ups: What is stopping you? • Is this you asking me out?
#98
easy

What is the best part of your morning routine?

Follow-ups: How early are we talking? • Would I survive it?
#99
easy

What is something you did this week that made you proud?

Follow-ups: Why does it matter? • Did anyone celebrate you?
#100
medium

What is an adventure you want to take before next year?

Follow-ups: Who is coming with you? • What is step one?
#101
easy

What is a dream you have had since you were little?

Follow-ups: Is it still alive? • What would it take?
#102
easy

Where do you see yourself living someday — city, suburbs, or countryside?

Follow-ups: Why there? • Would I fit in?
#103
easy

What is something you want to be famous for?

Follow-ups: Why that? • How close are you?
#104
medium

What is one thing you hope never changes about you?

Follow-ups: Why do you guard it? • Do I bring it out?
#105
medium

What is one thing you hope never changes about us?

Follow-ups: What made you say that? • What would you add to it?