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Essential Questions to Text Your Crush

70+ Things To Ask Your Crush Over Text in 2024

Feeling nervous about talking to your crush and want advice on what to ask them? Keep reading to find out the best things to ask your crush over text.

Ben Bailey
Ben Bailey

Roast Founder, Dating and AI Expert

Published July 4, 2023 -Updated March 4, 2024

Essential Questions to Text Your Crush

  • Discover 101+ essential questions to deepen your connection and ignite romance over text.
  • Break the ice and maintain engaging conversations that keep your crush intrigued and interested.
  • Unsure what to ask next? Get personalized, authentic lines that keep the conversation flowing and meaningful.

Once you've gotten your crush's phone number, it's time to figure out how to keep the conversation flowing and get them interested in you. You want to make a good first impression that will make your crush feel attracted to you, so it's essential that you ask your crush the right things to keep the ball rolling.


You can ask a romantic thing, to something funny or embarrassing like their celebrity crush. Make sure your questions match the mood and are interesting enough to move the conversation forward.


These are the best questions to ask your crush over text.

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Table of Contents

Here is the outline of the article, feel free to jump to the section that interests you the most.

  1. Simple Questions to Ask Your Crush Over Text
  2. Deep Questions to Ask Your Crush Over Text
  3. Funny Questions to Ask Your Crush Over Text
  4. Flirty Questions to Ask Your Crush Over Text
  5. Fun Questions to Ask Your Crush To Get Their Attention
Simple Questions to Ask Your Crush Over Text

Simple Questions to Ask Your Crush Over Text

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Start off the conversation with a few simple questions that will break the ice while still keeping things casual and light. By asking your crush a few simple things about themselves, you’ll be able to get to know them better without getting too personal and freaking them out. Girls appreciate a guy who puts in the effort to get to know them more, so your crush will definitely want to talk to you more if you ask about them.


  1. How do you like to spend your spare time?


  2. What are some of your hobbies and passions?


  3. What’s your favorite movie of all time — and why?


  4. Do you have a favorite meal to eat? What is it?


  5. What are your favorite places that you’ve traveled to?


  6. Do you like to read? Who is your favorite author?


  7. Do you have any pets? What are they like?


  8. Who do you consider your best friend? What are they like?

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Deep Questions to Ask Your Crush Over Text

Deep Questions to Ask Your Crush Over Text

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Want to get to know your match on a deeper level? Strengthen your bond and connection by asking personal questions that are respectful and will get her to open up about herself. Deep questions are the ideal type of questions to ask if you’re not looking for a casual hookup but rather are looking for something more like a long-term relationship.


These are the best deep questions to ask your crush over text.


  1. What’s your idea of the perfect date?


  2. What is something you’ve always wanted to do but haven’t?


  3. If you could travel to anywhere in the world, where would you go and why?


  4. If tomorrow, you could wake up with your dream job, what would it be?


  5. What is something you’re scared to do, but really want to do?


  6. If you could meet anyone—dead or alive, who would it be and why?


  7. What is one thing you don’t think you could live without?


  8. How would you describe your last relationship?


  9. Why did your last relationship end?


  10. What are some character traits you’re looking for in your next partner for a romantic relationship?


  11. Have you ever broken someone's heart before?


  12. What's your biggest fear in life?


  13. Are you looking for a serious relationship?


  14. What is your biggest deal breaker?

Struggling to craft the perfect answer?

Stuck on what to say next? Let ROAST experts take the lead! Next Line has analyzed thousands of successful conversations. In just a second, get irresistible answers to keep the conversation flowing.

Funny Questions to Ask Your Crush Over Text

Funny Questions to Ask Your Crush Over Text

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If you can make your match laugh, you’ll be in her good books and will be someone who she’ll be excited to keep the conversation flowing with. Humor is one of the best ways to not only break the ice and make your crush feel comfortable but to show yourself off in a positive light.


Tease your crush to answer truthfully, and make them laugh with a few silly questions that they'll love answering.


  1. What is the worst date you’ve ever been on?


  2. What’s your most embarassing moment? I’ll tell you mine if you tell me yours.


  3. Is there anything you consider to be your guilty pleasure?


  4. Describe the first crush you ever had, what were they like?


  5. What’s your favorite meme or gif of all time?


  6. If we were at a karaoke bar, what would your go-to song be?


  7. What’s something nerdy or unpopular that you love?


  8. What is your go to karaoke song?


  9. Describe your first kiss.


  10. Who was your first celebrity crush?


  11. Are you a dog or cat person?

Feel like your conversations lack depth?

With our analysis of thousands of profiles, we'll tailor your texting for maximum engagement and craft the perfect responses.

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Flirty Questions to Ask Your Crush Over Text

Flirty Questions to Ask Your Crush Over Text

Don't know what to say?

Try our Next Line generator to write the perfect response and capture hearts in a second!

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Want to be someone your crush can’t get out of their head? Send a flirty message to them to keep things hot and exciting. Girls love receiving compliments, and if she knows you’re flirting with her, she’ll feel a lot more comfortable talking to you and being flirty back. Make your crush feel special by sending her a flirty text that won’t fail to make her blush.


Here are the top flirty questions to ask your crush over text.


  1. What are the top 3 things you find attractive about a guy?


  2. If I could take you out right now, where would you want to go?


  3. What are your biggest turn-ons?


  4. Do you prefer kissing or cuddling?


  5. Do you like it when someone else makes the first move?


  6. If I cooked you a meal, what would your ideal meal be?


  7. What’s your best pickup line?


  8. What’s your favorite breakfast to have in the morning?


  9. What's your favorite sex position?

Feel like your conversations lack depth?

With our analysis of thousands of profiles, we'll tailor your texting for maximum engagement and craft the perfect responses.

Let ROAST add more personality to your profile with the Next Line.

Ready?

Fun Questions to Ask Your Crush To Get Their Attention

Fun Questions to Ask Your Crush To Get Their Attention

Tired of being ghosted?

Let us take care of it! Next Line will craft engaging responses for you in a second!

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Looking to get your crush's attention? Ask them a fun question they're not used to getting on dating apps that will show them you have the potential to be more than just friends. These fun questions will get your crush thinking and excited to answer.


Here are the best fun questions to ask your crush.


  1. What would you spend on if you had way too much money?


  2. What's your most embarrassing moment of the year?


  3. What's the most romantic thing someone has ever done for you?


  4. If you could only take 3 things to a deserted island, what would they be?


  5. What's your typical Saturday look like?


  6. Are you a morning or a night person?


  7. What's your love language?


  8. Tell me about your favorite childhood memory.

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Conclusion

Engaging in meaningful and playful texting with your crush in 2024 is more than just about saying the right words. It's about fostering an environment of mutual respect and interest, where you both feel comfortable being yourselves.


Every relationship is unique, and these questions should be adjusted according to the dynamics of your relationship. Pay attention to their responses, engage, empathize, and remember that the ultimate goal is not just to communicate, but to connect.


Happy texting!

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Ben ROAST

Ben Bailey

Ben is one of the best Dating Experts I've ever met and one of the few that cracked the algorithm of online dating. Every week, Ben is publishing new articles on ROAST, helping 20M+ of people to get more matches, dates, and find the one!

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