246 Really Flirty Questions To Ask Your Crush (While Texting)

Last Updated on December 14, 2021 by Alexander Burgemeester

You’re just starting to get to know each other. Everything feels exciting and maybe even a little scary. The good news is that asking the right questions can definitely elevate your dynamic to the next level. But what are some cute questions to ask your crush? And how do you ask those questions without seeming over-the-top or weird? 

You’re probably already exchanging messages nonstop, and you’re likely flirting here and there. Texting is an easy way to communicate, especially in those early stages. Being intentional with your conversation starters strengthens intimacy while also keeping things fun. Here are the best flirty questions to ask your crush!

Why Are Flirty Questions Useful to Get To Know Your Crush?

The act of flirting is a natural part of the mating process. It’s rooted in our biology and history, and it’s a primitive way we signal attraction to one another. 

Flirty questions allow you to get to know someone else. They take the pressure off needing to have a serious conversation. At the same time, they inadvertently can strengthen a sense of connection.

This makes for a great way to initiate the early stages of dating!

What Are Good Flirty Questions?

What Are Good Flirty Questions

Some of the best things to ask your crush include their take on certain romantic, sexual, or relationship-based content. 

This serves two purposes. First, it shows that you’re interested in knowing their opinion on intimate details. Second, it gives you useful information about who they are- which can help you decide if you want to actually pursue a relationship! 

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Good, flirty questions balance sexiness with curiosity. The flirtiness might be somewhat subtle at first, but the intentions usually become more obvious as things progress. 

How Do You Flirt Over Text?

How Do You Flirt Over Text

Flirting over text may be easier than flirting in person. Over text, you have time to think about and consider your responses. You can also read over what you write (and even send it to a friend to review) before blurting something out. 

Ideally, you want to keep messages short. You don’t want to overwhelm your crush with long-winded paragraphs. Flirting should also be positive and playful- you want to show off your good side!

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Finally, don’t overlook the benefits of a well-placed emoji. Whether it’s a wink, smirk, or kiss, those tiny images can make a significant difference in your tone!

50 Flirty Questions to Ask Your Crush

50 Flirty Questions to Ask Your Crush

Now that you know why flirting is important, what are some flirty questions to ask your crush? Here is a working list to get you inspired!

  1. What do you think about before you fall asleep?
  2. What makes for a perfect first date?
  3. How often do you think about me?
  4. How is someone like you single?
  5. Have you ever written something to me, but didn’t send it?
  6. What turns you on?
  7. What’s your favorite thing about being in a relationship?
  8. Would you rather never be able to kiss or never be able to cuddle? 
  9. What’s something you’ve never told anyone else?
  10. What traits would your ideal partner have?

  1. How would you want to know if someone likes you?
  2. What do you like the most about yourself? 
  3. Is everyone else in your family also really good-looking?
  4. What would you do if I called you in the middle of the night?
  5. What do you wear when you sleep?
  6. Do you even realize how much I like talking to you?
  7. How do you feel when we are together?
  8. What makes someone sexy to you?
  9. Have you ever dreamt of me?
  10. How would you respond if I asked you out tonight?

  1. Can I see you right now?
  2. Do you feel lucky that we met each other?
  3. What’s one thing you really want to know about me?
  4. What excites you the most about the future?
  5. How long does it take for you to feel comfortable with someone?
  6. Are you usually pretty open about feelings or more guarded?
  7. Can you see us spending more time together?
  8. What helps calm you down when you feel stressed?
  9. Would you ever do a long-distance relationship?
  10. How do you feel about meeting my friends?

  1. How would you get on my pet’s good side if you came over right now?
  2. What frustrates you the most about modern dating?
  3. Why are you single right now?
  4. What scares you the most about being in a relationship?
  5. What does trust mean to you, and how do you know when you trust someone?
  6. What’s something other people find fun that you don’t enjoy?
  7. If you only had one year left to live, how would you spend your time?
  8. What was the best vacation you ever went on?
  9. Have you ever really disappointed someone? What happened?
  10. Are you good at telling people how you feel?

  1. What’s one thing that’s on your bucket list?
  2. Have you ever failed at something that was really important to you?
  3. When is it appropriate to give up someone?
  4. How do you typically react when someone disrespects you?
  5. Do you think we text too much or not enough?
  6. When am I seeing you next?
  7. What makes me different from other people in your life?
  8. How close do you want us to be?
  9. What do you tell your friends about me?
  10. How would you feel if my family wanted to meet you?

25 Flirty Truths to Ask Your Crush

25 Flirty Truths to Ask Your Crush
  1. How do you know when you’re ready for a relationship?
  2. What makes you fall in love with someone?
  3. What’s your biggest weakness?
  4. Do you prefer cuddling or sleeping alone?
  5. What do you do when you get lonely?
  6. What’s your favorite part about me?
  7. Have you thought about me today?
  8. What’s your favorite outfit I wear?
  9. What songs remind you of me?
  10. What is an important boundary that you have in your relationships? 
  1. When do you know if you feel safe with someone?
  2. What’s something you have always wanted to try in the bedroom?
  3. Do you think it’s easy or hard for people to trust you?
  4. How long should people date before committing to a relationship?
  5. What always makes you roll your eyes?
  6. What is your biggest turn-on?
  7. What does true happiness mean to you?
  8. Would you consider yourself a good listener?
  9. If you were stranded on an island with only one person, who would it be?
  10. What’s a secret you’ve never told anyone?

  1. Do you have enough friends, or do you wish you had more?
  2. What kinds of things make you jealous?
  3. Is there anything you really want to know about me?
  4. Who would I most get along with in your life?
  5. If we could go anywhere in the world right now, where would you take me? 

25 Good Flirty Questions to Ask Your Crush

25 Good Flirty Questions to Ask Your Crush
  1. What’s the weirdest thing about you? 
  2. What was the best compliment you ever received?
  3. What makes you feel nervous? 
  4. When do you feel your happiest? 
  5. What do you most enjoy doing in your spare time?
  6. How direct would you want someone to be if they had feelings for you?
  7. What is the most important quality in a relationship for you?
  8. What is something embarrassing about you that people have found cute?
  9. What do you feel most passionate about in life?
  10. Would you rather plan a special date yourself or have someone plan one for you?
  1. Do you think people of the opposite sex really just be friends?
  2. How do you feel about physical affection?
  3. Would you rather go to a huge party with tons of people or a small get-together with a few people? 
  4. Do you like dirty talk?
  5. What are the most important priorities in your life right now? 
  6. What do you think we’d do if we had the entire night together?
  7. Where do you see our future?
  8. What is one accomplishment you’re really proud of?
  9. What would instantly make you feel unattracted to someone?
  10. What’s an important lesson you learned from a past relationship?

  1. Who was your first crush?
  2. What would your mom say about you if I asked?
  3. Can you send me a picture of what you’re wearing right now?
  4. What’s your favorite picture of me?
  5. What do you think about when you’re driving to work? 

25 Flirty and Intimate Questions to Ask Your Crush

25 Flirty and Intimate Questions to Ask Your Crush
  1. How do you define love?
  2. Would you rather be the little spoon or big spoon? 
  3. What’s something you wish you were good at?
  4. Who inspires you to be a better person?
  5. What career has always interested you?
  6. If you could do anything different, what would you have done?
  7. Who comforts you the best when you’re feeling sad?
  8. What was the first thing you noticed about me?
  9. What do you think you would do if I kissed you the next time I saw you?
  10. Would you say that you are more introverted or extroverted?
  1. What kinds of things keep you up at night?
  2. How would your best friend describe you?
  3. Would you rather spend a whole day with me or a whole night with me?
  4. What is important to you in a best friend?
  5. What’s a childhood memory that always makes you smile?
  6. How do you feel about the holidays?
  7. What things do you most enjoy doing alone?
  8. What is your love language?
  9. What is the best gift someone has ever gotten you?
  10. What instantly makes someone attractive to you?

  1. What’s something you feel scared of?
  2. What mistake have you made that helped you grow as a person?
  3. Would you rather chase someone romantically or be chased?
  4. What was the worst first date you ever went on?
  5. Do you fear rejection?

25 Flirty but Romantic Questions to Ask Your Crush

25 Flirty but Romantic Questions to Ask Your Crush
  1. What is something romantic you’ve always wanted to try?
  2. What does commitment mean to you?
  3. What romantic movie do you like the most?
  4. What couple in your family has the best relationship?
  5. What’s your favorite cheesy love song?
  6. If you could take me to any restaurant in the world, where would it be and what would you order?
  7. What’s the first thing you notice about other people?
  8. Do you think true love exists? 
  9. What’s the most embarrassing thing you did when you liked someone?
  10.  When it comes to liking someone, what would you say is your greatest weakness?
  1. What makes you smile?
  2. Would you rather people think you’re really funny or really kind?
  3. What would you want to do if I was at your place right now?
  4. How would you describe my personality if someone asked you?
  5. If you had all the money in the world, what kind of date would you want to plan?
  6. Do you like going to weddings?
  7. How do you like to help someone when they are going through a rough time?
  8. What should someone do if they start catching feelings for their friend?
  9. On a 1-10, how happy do you feel in your life right now?
  10. Are you more of a beach or mountain person?

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  1. If you had to present on any topic for an hour, what would you talk about?
  2. Who could you spend all day with without getting bored?
  3. What always makes you smile?
  4. What smell reminds you of me?
  5. What’s the best pick-up line that you know? 

25 Flirty and Cute Questions to Ask Your Crush

25 Flirty and Cute Questions to Ask Your Crush
  1. What’s the most romantic date you’ve ever heard of?
  2. Who is your celebrity crush? 
  3. What is your biggest deal-breaker in a relationship?
  4. What is the craziest thing that happened to you during your childhood?
  5. Would you rather be called sexy or smart? 
  6. What is your favorite place in the world? 
  7. How can you tell when you really like someone?
  8. What’s something you’ve tried that you’ll never do again? 
  9. If you could ask me anything, and I had to be truthful, what would you ask me right now?
  10. What animal most resembles you? 
  1. What is your biggest pet peeve when it comes to dating?
  2. What nickname did you have when you were younger?
  3. What always makes you laugh?
  4. How do you feel about girls making the first move?
  5. What if I asked to see you right now?
  6. What are you wearing?
  7. What’s the most embarrassing item that you own?
  8. What memory always makes you cringe?
  9. Would you rather I ask you fun questions or deep questions?
  10. Do your plans this weekend include me?

  1. What do your friends know about me?
  2. Do you think your pet will like me?
  3. What does your bed feel like?
  4. Do you prefer showering with someone or showering alone?
  5. If I were a total stranger, how would you try to impress me?

How Do You Play 21 Questions Flirty?

How Do You Play 21 Questions Flirty

21 questions is a popular party game where people learn more about each other through a series of questions. You can play with two people or several people. Depending on the rules, you can also allow for 1-2 “passes” where people can choose to skip answering specific questions. 

Basically, one person gets to ask the other person 21 questions in a row. When they are done, it’s the other person’s turn to ask. Most of the time, this game is played in person, but you can also play it while texting. 

So, what are the best 21 questions to ask your crush? Here is a sample script to get you inspired.

  1. Have you ever played 21 questions before?
  2. On a scale from 1-10, how nervous are you to play this game right now?
  3. What do you feel most nervous about me asking?
  4. Do you already know some of the questions you want to ask me?
  5. On a scale from 1-10, how much do you enjoy texting me?
  6. Do you think we text too much, just enough, or not enough?
  7. Do you think we see each other too much, just enough, or not enough?
  8. What is your favorite thing to do with me?
  9. What’s something you really want to try with me?
  10. What’s something you definitely don’t want to do with me?

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  1. If you were in charge of planning the best day of my life, what would we do?
  2. What do you think about my body?
  3. Do you have any fantasies you want to share?
  4. What do you like the most about me?
  5. Would you change anything about us right now?
  6. On a scale from 1-10, how nervous do you still feel playing this game?
  7. What question are you hoping that I ask you?
  8. What two words most describe me?
  9. What two words most describe you?
  10. How satisfied do you feel with your overall life right now?

  1. What do you think is missing from your life?
  2. Do you feel like we understand each other?
  3. What’s your favorite inside joke that we have?
  4. How did you feel when you first met me?
  5. How does imagining the future with me in it sound to you?

What Are Some Juicy Questions to Ask Your Crush on Chat?

What Are Some Juicy Questions to Ask Your Crush on Chat

Are you really ready to dial up your conversation with your crush? First, it’s important to ask yourself how things are already going. For example, are you relatively confident that things are going well? Do you have some pretty clear evidence that your crush is also interested in you?

If so, here are some of the best, juiciest questions to ask your crush while texting. 

  1. Where’s the strangest place you’ve ever had sex?
  2. How do you make sure that you please your partner in the bedroom?
  3. What makes sex really good for you?
  4. Do you have any regrets about past partners?
  5. How did you lose your virginity?
  6. Are you a big kisser?
  7. What does making love mean to you?
  8. If we had an entire weekend together, what would you really want to do?
  9. What’s something you never want to do during sex?
  10. What was the worst sexual experience you’ve ever had?

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  1. Do you like to listen to music during sex? 
  2. How do you feel about lingerie?
  3. Have you ever been caught having sex? What happened?
  4. What kind of porn do you like to watch?
  5. Can a friends-with-benefits ever become something more?
  6. How often do you prefer to have sex?
  7. Have you ever watched your partner masturbate? What was that like for you?
  8. How direct are you with what you want in the bedroom?
  9. Do you consider yourself more submissive or dominating?
  10. What do you think about role-playing?

  1. In your opinion, what’s the best thing to do just after sex?
  2. Do you like when your partner uses dirty talk?
  3. Would you ever have a threesome or orgy?
  4. What kind of sex toys do you enjoy using?
  5. Have you ever had a sex dream that freaked you out?
  6. What celebrity would you love to have sex with if you had the chance?
  7. What’s your favorite sex position?
  8. Do you like foreplay?
  9. Would you rather have sex with the lights on or lights off?
  10. Do you have any fetishes you want to share with me?

  1. What do you think about one-night stands?
  2. Would you rather sex be slow and sensual or fast and rough?
  3. What do you think you’re most skilled at in the bedroom?
  4. Would you rather have sex in the morning at night?
  5. What do you think about having sex in the shower?
  6. What would turn you off right away in the bedroom?
  7. What does it feel like when I go down on you?
  8. How do you prefer I touch you?
  9. Do you want to know what I’m thinking about right now?
  10. If you could only kiss me in one place, where would it be?

  1. What’s a fantasy you haven’t told me about yet?
  2. If I told you I was horny right now, what would you say?
  3. How does it feel when you kiss me?
  4. Have you ever touched yourself thinking about me?
  5. What outfit of mine turns you on the most?
  6. Do you like making eye contact during sex?
  7. Have you ever played a dirty version of truth-or-dare? Would you want to?
  8. How do you like your partner to groom themselves down there?
  9. What was the last dirty dream that you had?
  10. What’s the longest you’ve ever gone without having sex?

Final Thoughts 

The best questions to ask your crush while texting are questions that feel mostly appropriate but somewhat edgy. In other words, you don’t want to come across as hypersexual or overly nosy.

Doing so could be a turn-off, and it might result in your crush thinking that you’re only interested in sex.

Instead, it’s much better to balance romantic, flirty, and serious questions. Try to go with the flow, but don’t hesitate to take risks! All good relationships start with taking a risk.

The more you get to know your crush, the more you will get a feel for what is and isn’t right. 

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Alexander Burgemeester

Alexander Burgemeester has a Master in Neuropsychology. He studied at the University of Amsterdam and has a bachelor's in Clinical Psychology. Want to know more?

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