53 Deep, Flirty And Fun Questions To Ask Your Crush While Texting

If you are texting your crush and you are not quite sure what to say, we have got you covered. Talking through text presents some challenges. For one, tone can be hard to decipher, which is accurate from both sides. Still, you can send some tested and proven texts to start a conversation or keep an existing conversation flowing smoothly.

So, if you are wondering what the next message or questions to ask your crush should be, look no further. Read the questions we have included below, and see which ones you feel like sending. Choose a few now but save this page and come back later for more texting inspiration.

Things to Ask Your Crush Over Text

We have included interesting questions below—some deep, flirty, and fun, so you have many to choose from. Explore our suggestions below and figure out which type of text you should send.

18 Deep Questions to Ask Your Crush While Texting

These questions will give you a chance to learn a lot about your crush. If they do not want to answer a particular question, that is fine. It takes some of us a lot of time to feel comfortable with someone to share personal details about our lives. As such, feel free to let your crush know that when you ask these questions, there is no pressure to answer them.

Questions To Ask Your Crush While Texting, flirty questions

1. What is the most important lesson you have ever learned?

Jump right in. This is a huge question and one that rarely has a simple answer. They might answer with a summary, but it has an interesting background. This is a great question to ask if you want to deepen the conversation and open the possibility of cultivating an emotional bond. The response to this question might be lengthy, so be ready for it.

2. Who is the closest person in your life?

Who do they share most of their time with? Who knows the most about them? They will probably talk about their family or childhood friends. If they have someone close to them, make sure to ask some more questions about that person, so they know you are interested.

3. Have you ever been heartbroken?

You might not want to bring up painful memories from the past, but hopefully, by now, they have moved on and are ready to talk about this. Have you ever been heartbroken? If yes, then you can sympathize with them. If not, ask them what it is like. Ask them about the most significant lesson or realization they gained after the heart-breaking experience they had.

4. Where do you see yourself in ten years?

Knowing where your crush sees themselves in ten years might give you some insight into how much room they have for you in their life. Do you guys share similar goals? Could you be living similar lives in ten years? This question will give you a high-level view of a potential future relationship with your crush.

5. What makes you feel better when you are down?

It is always a nice question and a helpful reminder of what they need if they are not feeling great. If you two see each other more often, then asking this question will help you help them when they need it. Also, this is an opportunity to discover a person’s mood booster and the reason behind it.

6. If you could change something about yourself, what would it be?

With this question, you run the risk of bringing up some insecurities. Still, you do not have to get lost in those insecurities. Keep the conversation light and offer compliments if the person has a negative opinion of themselves. If you have been looking for an opportunity to compliment, this question is your way in.

7. How do you feel about your family?

This is one of the more profound questions—how someone feels about their family usually has a lot of backstories, so this question is a great way to begin a lengthy conversation. You can ask about it over text, but this one might be a good question to ask when you have a chance to talk in person.

8. How do you feel about religion?

This is a great question because it can tell you a lot about their values and beliefs. It also works neutrally—it does not ask, ‘are you religious?’ or ‘what is your religion?’ Instead, it gives the person a chance to explain their stance on religion in general. Respect is the key when it comes to this topic.

9. How do you feel about politics?

Similar to the question on religion, this one is not to start a debate or question someone’s belief. Instead, it opens up space to talk about politics if you both want to, but it does not pressure you to go any further on the topic. Politics can be a touchy subject, and a very divisive one, so be mindful of how you approach this part of the conversation. Again, respect is the key when it comes to this topic.

Questions To Ask Your Crush While Texting, flirty questions

10. What is your biggest fear?

This can be a deep question but also a fun one to ask. Some people will freely admit that their biggest fear is being alone forever, while others go for a lighter answer and say ‘spiders!’ Either way, this question is insightful and will lead to more stories. That is what you want from a question— encouragement to talk more.

11. What is the most significant dream you have ever had?

Dreams can be highly personal, and anyone who likes to talk about their dreams will love this question. If they do not seem interested in the question, that is the end, but if they want to talk about dreams, take it as an opportunity to text for hours.

12. What is the weirdest dream you have ever had?

Weird dreams can tell a lot about a person. Not just the content of their strangest dream, but also how they feel about it. If you are inclined to analyze dreams, you can bond over dream-related questions and stories. The weirder and more fantastical, the better!

13. What do you look for in a relationship?

This one might not be the best question to start with, but if you have been texting for a while now, then it is worth asking. If this is someone you have a crush on, you will naturally be interested in their views on relationships. Getting to know what they are looking for will give you a better idea of whether or not you two are compatible.

14. Why did your last relationship end?

This is a highly personal question. So, again, it is probably best to keep this for a few weeks into your conversation. Do not ask this question right away because there may be nuances to the relationship’s end that you might not fully understand until you know this person a little bit better. It is never easy to tell how sensitive the person is about their previous relationships if you are just starting your conversation with that person, so ease into the question rather than jumping straight in.

15. Who is your best friend in this crazy world?

Asking about someone’s best friend is a surefire way to open up a bigger conversation. They are sure to have some funny, crazy, or heartwarming stories about why that person is their best friend. This is also a great way to help the other person relax and take the focus off them for a minute.

16. Are you looking for a serious relationship or something casual?

This might be a question you want to ask. This can feel awkward to ask, but asking this question will determine the direction of the potential relationship you might establish with your crush. So, if you want to know if there is potential for something serious, but they are adamant and only want something casual, you learn to stop looking for a serious relationship with that person.

17. What is your favorite childhood memory?

This is one of the most exciting questions on the list, and its answer is bound to be a long and exciting story. When people talk about their favorite childhood memories, they typically get a warm feeling of nostalgia, and sharing that with you is sure to bring the two of you closer.

18. What was the most significant thing you learned from a past relationship?

This question will give you a lot of insight into the other person. We all go through relationships, and if we are mindful enough, we learn something valuable that we can then apply to our future relationships. Ask this person something interesting they learned from a past relationship, but remember to share your lessons too. Otherwise, the imbalance will feel unfair.

Questions To Ask Your Crush While Texting, flirty questions

23 Flirty Questions to Ask Your Crush While Texting

Flirty questions are a great way to gauge the dynamic between you and your crush, and the thrill can be addictive. You send a flirty text, and you do not always know how it will go. You wait nervously for a reply and get excited when they text back. I am sure you get even more excited when they flirt back.

Flirting is fun, but it can also lead to even more fun, and it is also a great way to develop a more intimate and personal connection with someone. So, check out this list of flirty questions you can use in a text conversation and have fun!

  • Do you believe in love at first sight?
  • What is your idea of a perfect date?
  • What do you find most attractive in a person?
  • What do you find most appealing about yourself?
  • What is your ideal partner?
  • What is the craziest secret you have today?
  • What is the best pickup line you have ever heard of?
  • Do you prefer making the first move? Or do you like it when the other person makes it?
  • Do you have a sexual fantasy?
  • Do you think you are romantic? Why do you think so?
  • What is the most romantic thing you have ever done?
  • How are you still single?
  • Do you like tattoos?
  • What do you want to know about me?
  • If you could go anywhere in the world, where would you go?
  • Do you sleep with clothes on or clothes off?
  • What is your favorite thing to wear on special occasions?
  • How do you feel about me?
  • Do you find me attractive?
  • What do you think about sex before marriage?
  • What song do you think best describes me?
  • What turns you on?
  • What turns you off?

12 Fun Questions to Ask Your Crush While Texting

Here are some conversation starters you can use to keep the conversation light.

  • Who is your first celebrity crush?
  • What is your most embarrassing moment or memory?
  • What is your favorite word?
  • What is your favorite movie?
  • If you could invite three celebrities to dinner, who would they be?
  • What is your favorite holiday destination?
  • Would you rather…? (This one can keep a conversation going for hours!)
  • What was your first impression of me?
  • How would you like to spend your money?
  • If you had a million dollars, how would you spend it?
  • Where would you live if you could live anywhere in the entire world, where would you live?
  • If you could change your name to a different one, what would it be?


Getting to know someone over text is far from the same as getting to know them in person, but it can be a fun and exciting way to do it and is a great way to get a sense of a person before you eventually meet up with them. More and more of us are using social media and online dating apps to meet people, given the new post-pandemic normal.

If you are not a fan of texting, these questions should help you get into the swing of things. It is always good to have some questions prepared to keep a conversation going when it starts to dip. So remember a few of these questions, save them, or save the page and return to refresh your memory whenever you are stuck for something to say in your next text conversation with your crush.

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