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45+ Questions to Ask Your Crush for a Meaningful Conversations -Tested and Approved

You're into someone, and now you're trying to get your crush's attention. Here are some conversation starters to help break the ice and get to know them better.
Best Questions To Ask Your Crush Over Text

You've got a crush.

You feel those butterflies in your stomach every time you see them. Maybe you blush, and your heart starts beating fast. You feel like you're younger self all over again, lacking the confidence to make the first move. After all, what if they're not into you? Worse, what if you find out you're not really interested in them?

Here are 46 questions to ask your crush to help you get to know them and decide if you want to take things to the next level.

Whether you're using Tinder, online dating, or texting someone you know in real life, you'll be more comfortable in no time and ready to ask them out.

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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. How to Approach Asking Your Crush Questions
  2. Conversation Starters for Your Crush
  3. Getting to Know Your Crush Better
  4. Making a Good Impression on Your Crush
  5. Fun and Engaging Questions for Your Crush
  6. Building a Connection through Meaningful Conversation
  7. Flirty Questions to Gauge Their Interest
  8. Dirty Questions to Get to the Point
How to Approach Asking Your Crush Questions

How to Approach Asking Your Crush Questions

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There are different ways to approach asking your crush questions, so it's important to understand what you're trying to accomplish.

  • Are you trying to get to know them better? Ask deep questions that prompt meaningful responses.
  • Are you trying to make them laugh? Ask them funny questions to see if you have a compatible sense of humor.
  • Are you trying to make yourself look good? Ask them questions that will make a good impression and showcase your best assets.
  • Are you trying to get them home with you? Ask them flirty questions to make sure you're on the same page.

Targeting the questions you ask your crush will help you get to your end goal, whatever that may be.

Once you decide what type of questions to ask your crush, now you want to make sure that they make sense to the other person.

  • Personalize your questions so they make sense to your crush, though you'll want to use their name directly sparingly. Some people can find that creepy.
  • Focus on your crush's interests. They will be more likely to talk and appreciate that you pay attention to them.
  • Keep questions open-ended so it keeps the conversation flowing. There's nothing worse than one-word answers when you're trying to keep a conversation going.
  • When in doubt, make them laugh. If you're not sure where to start, crack a joke. It's a fantastic way to break the ice. Just keep it clean - for now.

It's normal to be nervous at first, but once you start talking, the conversation will start to feel more natural.

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Conversation Starters for Your Crush

Conversation Starters for Your Crush

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If you're still testing the waters, here are some basic conversation starters to ask your crush. Once you learn more information, be sure to use the details to ask follow-up questions to keep the conversation going.

  • What are some interesting hobbies you have? This question can help see if your interests align - or help broaden your horizons to explore new ones.
  • What's your favorite movie? What's your favorite TV show? These questions will help you learn if you're going to binge the next big series together or catch the latest blockbuster. It will help see if you have common interests and open the conversation up for further discussion about everything from your favorite characters or why a character is the worst.
  • What kind of music do you enjoy listening to? You can follow it up by asking who their favorite musical artist is, what their favorite song is, what the best concert they've ever seen, and so on. Musical preference is a great way to make people feel more comfortable because they've often got a lot to say.
  • When was the last time you spent way too much money? This is a fun one to see what they like to buy themselves or spend their time. You can learn if they are more of a thing person or an experience person.
  • If you could meet one famous person, dead or alive, who would it be and why? Learning about a person's heroes can tell you a lot about the person they aspire to be.
  • Tell me something about yourself in ten words or less. This is an open-ended question that the person can take anywhere! It also takes thought to boil something down to just a few words, so they have to consider their fact carefully.

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Getting to Know Your Crush Better

Getting to Know Your Crush Better

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Perhaps you want to get to know your crush on a deeper level. You want something more than just a hey to open the conversation. Here are some questions that you can ask to start building a connection.

  • How do you like to spend your free time? Kind of like asking about their hobbies, this question will help you understand your crush's interests and how they like to relax or have fun. Bonus points if you use this question to plan your first date!
  • What's your favorite food? This can help you learn where to take them on a dinner date if you decide to take it to the next level. If it's a different type of food than yours, you can always try yours next!
  • What's your guilty pleasure? Depending on the context, this can also be a flirty question, but it's a fun one! Maybe they like to eat a pint of ice cream or binge reality TV. Whatever it is, it can tell you a lot about how they like to unwind.
  • Are you a morning or night person? This can help you learn when they are most active. If they're a night owl, then they may not respond as quickly in the morning.
  • What are your dreams and aspirations? This is a loaded question, so maybe don't start with it right out of the gate! This helps you understand your crush's goals and ambitions while providing insight into their personality.
  • What is your favorite childhood memory? This question can help evoke nostalgic feelings, giving you an opportunity to bond over how you were raised or trade childhood stories. This creates more intimate conversation and can lead to some really personal discussion, so use it with care.
  • What's on your bucket list? This question can help you understand your crush's far-reaching goals. And, what they tell you can help you understand a lot about their long-term goals and aspirations.

Struggling to craft the perfect answer?

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Making a Good Impression on Your Crush

Making a Good Impression on Your Crush

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Sometimes you just want to make a really good impression with your crush. You want to showcase your best sides while demonstrating genuine interest in them in a person. Here are some deep questions that you can ask to do just that.

  • What qualities do you value most in a person? This is a really personal question that can help highlight a person's values. If yours matches, you're in the clear. If you still have work to do, you can help align your behaviors accordingly. Just remember to never pretend to be someone you're not. It never ends well.
  • How do you handle stress or difficult situations? As much as we'd like to avoid stressful situations, they happen. How we react to them can tell a lot about us as a person. It helps show how they cope with challenges and demonstrates empathy that you care enough to ask.
  • What is something you're passionate about? Everyone has a special interest. Something they can talk about forever if needed. Asking this question allows them to share their interests and passions. It also shows that you care enough to ask and value their individuality - and their interests.
  • What's the most romantic thing that happened to you? This question shows that you're trying to learn their love language. You want to understand what they like and don't like, as well as how they like to receive attention. You can also get ideas on how to woo them!
  • What's your elevator pitch in a job interview? This may seem a little boring, but it's a great way to learn more about what they do for a living. Everyone has an elevator pitch! And after, you can ask more probing questions.

Feel like your conversations lack depth?

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Fun and Engaging Questions for Your Crush

Fun and Engaging Questions for Your Crush

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Conversations don't always have to be deep, meaningful, and heavy! You can also ask them fun and engaging questions to help break the ice and set the tone for your interactions. Here are some lighthearted and entertaining questions to ask your crush to keep the conversation enjoyable.

  • If you could have any superpower, what would it be? Everyone has thought about what it would be like to have magical powers. This question sparks imagination and can lead to a playful discussion about what-ifs. You can also tell a lot about a person based on the answer!
  • What's your most embarrassing moment? This question shows that they don't take themselves too seriously! It creates a fun and humorous atmosphere, and you can trade funny anecdotes back and forth. This embarrassing moment can become a bonding moment before you know it!
  • If you could travel anywhere in the world, where would you go? Some people are passionate about travel. Whether they've visited all over the world or simply dream about it, you can plan your future travels together through your shared wanderlust.
  • What's the worst lie you've ever told? Approach this in a funny and casual way. You don't want to accidentally open up a can of worms!
  • What's your go-to karaoke song? Not all people like the limelight, but most people have a song they love to scream at the top of their lungs. You can even plan a date to hear it in person.
  • Who's your celebrity crush? Whether current or past, this can help you see what the other person likes without directly asking. Just don't take it personally if their celebrity crush looks differently than you! Ask them what they like about the person. The answer may surprise you!
  • What's the craziest thing you've ever done to get someone's attention? This shows you just how far they're willing to go for love! You can also swap stories about an embarrassing thing that you have done for love.
  • What's the worst date you've ever been on? You can laugh about the hijinks that happened and also learn what to avoid!

The Perfect Icebreaker Is Just a Click Away

Found your perfect match and don't want to mess it up? Let us analyze their profile and craft the perfect icebreaker to ensure an engaging conversation!

Building a Connection through Meaningful Conversation

Building a Connection through Meaningful Conversation

Feeling invisible?

Be unforgettable with Next Line: the perfect conversation starter.

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If you're certain that you want your crush to be more than that, you want to have some questions to ask your crush that promote deeper conversation. You want to establish a stronger bond to move from just friends and take things to the next level.

  • What is your biggest fear, and how do you overcome it? This question promotes vulnerability, so not all people will feel comfortable discussing it. However, it can help you learn so much about a person and allow you to avoid behaviors that can help reinforce their fears. They may not have successfully overcome it, but you can help them manage through it together.
  • What is the most important lesson you've learned in life so far? This question makes you think. It forces them to be introspective and reflect on their life experiences and share valuable insights that they learned. You can learn from them and trade yours back and forth.
  • How do you define success, and what are your goals in life? Personal milestones are important. It shows that people have goals and want to keep pushing forward. You can see if your ideas of success align. If not, that's not always a bad thing! These can change over time.
  • What's your biggest deal breaker in a new relationship? Everyone has something that gives them the ick, so you want to know what your crush's is and how to avoid it.
  • What did you learn from your last relationship that will help you in your next relationship? People learn and grow from every experience, so discussing what you learned from a relationship end can provide new insight and perspective on future relationships.
  • When was the first time you had your heart broken? Learning about past relationships is a great way to build a deeper connection.
  • What's your life's philosophy? Most people have a personal mantra. Asking someone what it is can help you learn more about what they value and what they want to project into the world.
  • What's the best compliment you've ever received? You can learn about what the person values, as well as how to praise and compliment them in the future. File it away for future reference.

The Perfect Icebreaker Is Just a Click Away

Found your perfect match and don't want to mess it up? Let us analyze their profile and craft the perfect icebreaker to ensure an engaging conversation!

Flirty Questions to Gauge Their Interest

Flirty Questions to Gauge Their Interest

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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Sometimes, you don't want to take yourself too seriously! You just want to flirt with your crush. Maybe that gets them home with you. Maybe you're just building anticipation. Regardless, here are some questions to ask your crush.

  • Who was your first kiss? Bonus points if you follow up to their answer with the question, "Want me to be your last?" Asking someone about their first kiss can be a fun way to reminisce, swap stories about the past, and laugh about past relationships.
  • What's your dream date night? Hopefully, it's something that hasn't happened yet, and you can make it a reality! Not only does it demonstrate active listening when you bring it to life, but it's also a fun way to make her dreams come true.
  • What's your love language? You'll learn a lot about how they like to receive affection when you ask this question.
  • Do you want kids someday? Want to start trying? This is a funny question that can help break the ice and transition to a more flirty conversation while still helping you learn more about the other person.
  • If you could pick one physical attribute that's your favorite, what would it be and why? Depending on how they answer, this could be fun and flirty. Direct the question to get a flirty response and tell them how much you agree. Ask to see some pictures!
  • Do you like to make the first move? This question can help you learn how your crush likes to be pursued. Some like to be chased, while others like to be the aggressor.

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.

Dirty Questions to Get to the Point

Dirty Questions to Get to the Point

Intimidated by texting?

Relax! Next Line will analyze and craft the response for you!

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Perhaps you're tired of beating around the bush with your crush, and you want to get straight to it. Here are some questions to ask your crush to assess if you're sexually compatible.

  • What's your sexual orientation? This may seem like an obvious question, but sometimes you just want to make sure! If you want to add other partners to the bedroom, now's a good time to share those expectations.
  • What's your biggest guilty pleasure ... sexually? This one helps you learn what dirty little secrets your crush may be hiding and how you can help them meet them.
  • What's your favorite sex position? Everyone has their go-to, and you can see if you like the same things or if you're up for trying something new.
  • Are you a top or bottom? Enough said.
  • **What's the best dirty picture you've ever taken? **This opens the door to some serious sexting.
  • What's your orgasm record? Follow it up with a challenge to beat it. Just make sure that you deliver on the promise!
  • Do you have any sexual kinks? People like what they like, so it's best to understand right out of the gate if you're sexually compatible. If you've never tried something, be open to experimentation! You never know if you'll like something unless you try it.

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Conclusion

Striking up a conversation doesn't have to be stressful when you have these conversation starters in your back pocket.

Consider what your intent is, and just go for it!

Have fun as you chat up your crush - you've got this!

Before you leave, make sure you stand out more in the dating scene!
Put your best foot forward. Click to create the perfect icebreaker that will put you at the forefront of the dating scene. Get ready for 10x more dates!

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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