35 Cute Questions To Ask Your Crush While Texting

questions to ask your crush

Thinking of questions to ask your crush while texting is an art trickier than you think. Texting is a medium where you can easily bore the other person without even realizing it. Since attention is so limited and elusive, texting can quickly fizzle out or become a tedious process to keep up with. 

Interestingly, wooing someone over text also has its advantages. Texts allow you more confidence and enable you to bring out parts of your personality that you might not be comfortable putting forth in person. So, if you want to try some smooth questions to ask your crush, then texting might be a great place to start.

Knowing the right topics to talk about over text can make all the difference in your efforts to win over your crush. So, it is worth thinking about questions to ask your crush over text to start a conversation or wooing them with the right combination of memes, GIFs and jokes!

35 Questions To Ask Your Crush While Texting – Know If They Like You 

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Wooing itself is a long and arduous process. Doing it over text makes it all the more complicated. But, if done right, it can also be a lot of fun. The right questions to ask your crush while texting can allow you to impress them, get to know them better and gauge whether they like you. 

The key is to keep them engaged, leave them asking for more, and do it in a way that helps them understand you in the process. Sounds complicated? It’s not. There are some really simple ways to make conversation easy with your crush. These 35 questions to ask your crush while texting are proof that it’s not as complex as it may sound: 

1. ‘What’s your biggest deal-breaker when dating?’ 

You are jumping right into deep waters with this one. One of the questions to ask your crush to see if they like you is this one. This will help you get to know their dating preferences, likes and dislikes. This is one of the best questions to ask your crush over text to start a conversation, and also gives you a direct window to talk about dating and relationships.

Related Reading: 21 Do’s And Don’ts When Dating A Widower

2. ‘What’s on your bucket list for this year?’ 

This question keeps it light and casual while ensuring the conversation is fun. Your crush will be inclined to answer this question because it’s not too personal but lets out just enough about them. This is definitely one of the perfect questions to ask your crush while texting to get to know them better.

3. ‘Are you a mountain or a beach person?’ 

This should be on your list of questions to ask your guy crush while texting. Almost everyone likes to travel but instead of asking that question directly, use this variation instead. Depending on their response, you can ask your crush about their trips and maybe tell them about your own. If you’re lucky, you can even plan some travel for two!

4. ‘What do you think about after 2 glasses of wine?’ 

Looking for flirty questions to ask your crush while texting? The best thing about asking this question is that it can go a lot of ways. It can go a really fun way, bring out their sexy side or make the conversation deep and intellectual. Try your luck and find out!  What to ask your crush when texting? Put this in the top 5!

make conversation easier with your crush
Make conversation easier with your crush by asking them some personal questions

5. ‘Are you on the naughty or nice list this Christmas?’ 

Naughty or nice? This is the perfect question to ask around the holiday season. This question is perfect as it allows them to tell you whatever they want. The ball is immediately in their court. This is also one of the flirty questions to ask your crush while texting, especially if you’re standing around mistletoe.

6. ‘What is your biggest pet peeve?’ 

To really get to know your crush, this question is super important. It is necessary to know their likes, dislikes and general social preferences to understand them better. This question will help you do exactly that. 

7. ‘How do you picture yourself in the next 5 years?’ 

This question can be the gateway for a long, intense conversation. One of the topics to talk about with your crush over text is your future plans and where you see yourselves going. 

8. ‘Tell me your worst dating story’

One of the questions to ask your crush while texting to get to know them is this one if you want to dig into their past directly. This could end in some good laughs and interesting revelations. This is also one of the more interesting questions to ask your girl crush while texting so you know what not to do on a date.

9. ‘Is love or money more important to you?’ 

To get to know your crush on a deeper level, try this one out. This simple question can tell a lot about a person just by the way they answer it. This is one of the good questions to ask a guy while texting to understand what he prioritizes in life and whether he is your type at all or not.

10. ‘Have you ever been cheated on?’

Some of the questions to ask your crush while texting can be about how they deal with heartbreak or poignant experiences. Wait until you’ve established a certain comfort level with them before you jump into a strong question like this. 

11. ‘What is your biggest turn on and why?’

To keep things going hot and to test your sexual chemistry, try this question out when you feel the time is right. This type of question can help you gauge whether there is sexual tension between you both or not. One of the perfect flirty questions to ask your crush while texting, try your luck with this one soon.

Related Reading: 30 Sexy, Dirty Text Messages For Your Boyfriend

12. ‘If you could eat one thing for the rest of your life, what would it be?’

When you’re wondering what to ask your crush while texting, try this one out. If you’re both foodies, this could lead to an engaging and passionate conversation. Furthermore, you can easily suggest a date following this one. “I’ll take you out for the best pizza in town and you will change your mind’’ is a smooth way to ask them out. 

funny question
Ask your crush funny questions to make them ponder and laugh

13. ‘Are you an indoors or outdoors person?’ 

The answer to this is the manual for planning your dates. Know what your crush likes and what they prefer to do in order to plan exciting dates for them. This could be one of the questions to ask your crush over text to start a conversation and reel them in!

14. ‘What is your poison?’

This is an old fashioned way of asking someone what kind of alcoholic drink they prefer. If you both like to drink, this question can truly help you bond and get you guys drinking together!  

15. ‘Do you believe in soulmates?’ 

This can be a groundbreaking question as it can lead to a lot of follow up questions and deeper discussions. An exchange of views, opinions and experiences is essential to get to know your crush well. This could be one of the deep questions to ask your crush while texting so ask away and see if you have a soul connection!

16. ‘If your phone was broken and it could only play one song, what would you choose?’

This appears to be one of the funny questions to ask your crush, but in reality, it does not have a simple answer. Our music preferences tell a lot about who we are as people. This subtle question will give you an insight into your crush’s personality. 

17. ‘What superpower do you want to have?’

It could be invisibility, flying or time traveling. This may seem like a childish question but one that almost everyone will be game to answer. This definitely makes our list of fun questions to ask your crush over text to start a conversation. Also, if their answer is, ‘I want to be like the Hulk’, you might want to back away slowly.

good questions to ask a guy while texting
Ask these questions to a guy while texting to keep him interested

18. ‘If your life was a movie, what would you call it?’

Naming your life the way you would name a movie is a short and sweet way to sum it up without giving out any actual details. This is one of the flirty first date questions you can ask!

19. ‘Who is the one person you cannot live without?’

To understand your crush better, you must know who they consider indispensable in their life. This is a question to ask your guy crush while texting and see if it’s their mum, their dog or a cardboard cutout of Scarlett Johansson.

20. ‘What is the one thing you want to change about yourself?’ 

Questions to ask your crush while texting do not always have to be lighthearted or circling the edges. Once you two are close, you can try to get them to open up to you with such deep questions.  This is also one of the questions to ask your crush while texting to impress them with your psychological insights.

21. ‘What keeps you up at night?’ 

It could be their passions, moments of self-introspection, an old heartbreak or a desire to change something in the world. Ask this question late at night to dive into some charged conversations. 

22. ‘Do you like your job?’ 

It is always nice to understand how your crush is doing in life and whether they like the trajectory of their journey so far. This is just not to make conversation, but it also helps you judge whether they’re the kind of person you want to be with. 

23. ‘How does one sweep you off your feet?’ 

One of the questions to ask your crush to see if they like you is this one! It is pretty indirect but if they indicate that you should do something for them, they are definitely flirting back with you! This is also one of the most wonderfully romantic questions to ask your crush while texting.

Related Reading: How To Impress A Girl On A Date And Make Her Want To Go On More

24. ‘Do you have an embarrassing hobby?’ 

This cute question can open up a chest of embarrassing stories and feelings. Trying to know your crush is also about knowing their quirks just as well. 

25. ‘Do you believe in superstitions?’ 

If they do, they probably have some eerie stories to back it up! Not all conversations have to be personal or romantic. Some can just be plain awe-inducing. 

26. “Scuba-diving or skydiving?”

Here’s a question to ask your girl crush while texting. Get to know how adventurous your crush is by asking them this question. If luck is on your side and the conversation goes well, you can plan to embark on a travel adventure together. Specific questions like this also leads to specific plans, which, let’s face it, is what you want.

adventure with your crush
Plan an adventure with your crush!

27. ‘What are the signals you give someone when you like them?’

Need smooth questions to ask your crush and show them you’re interested? One of the questions to ask your crush to see if they like you is this. They may not directly give away how they feel about you with this one, but if there is a vibe going, you will certainly know. 

28. ‘What’s a fashion trend that makes no sense to you?’ 

Keep the conversation light and fun by bonding over all the odd fashion statements you see around. Sometimes, disliking the same things can help you get closer to someone more than you think. This is also one of the best questions to ask your crush while texting to impress them with your knowledge of fashion and sense of humor.

29. ‘What is the craziest place you’ve had sex?’

When you’re in a raunchy mood, drop this question to see if there is room for some sex talk. Use this question to know how wild and experimental your crush truly is. This is indeed one of the good questions to ask a guy while texting if you want to see their naughty side. If you’re looking for flirty questions to ask your crush while texting, look no further!

smooth questions to ask your crush
Thinking of smooth questions to ask your crush?

30. ‘What is one thing nobody knows about you?’ 

To know their deepest, darkest secrets you can try this question over text with your crush. There is no guarantee how far your luck will take you but there is no harm in showing a little interest. 

31. ‘Which fictional character do you relate to?’

This is one of the best questions to ask your crush while texting because we all internally resonate with one fictional character or the other. Plus, this gives out a lot of clues about their personality. This is a great question to ask your guy crush while texting to see whether he’s a Mr. Darcy or a Gatsby. Make conversation easier with your crush by using this on them tonight.

32. ‘Are you a forgiving person?’

To really get to know their nature, ask them if they are forgiving or if they hold grudges for a long time. Do it in a gentle way to avoid touching a sensitive nerve or bringing up a topic that might be too personal. 

Related Reading: What Is Forgiveness In Relationships And Why Is It Important

33. ‘What is the last lie you told?’

This question is cute, funky and undeniably controversial but in a good way. Ask your crush and if they tell you, they are clearly very comfortable with you. 

questions for crush
Text your crush and ask them what was they last lie they told to keep the fun going

34. ‘Have you ever fallen for a close friend?’ 

This is one of the questions to ask your crush while texting to open up a different side of them. Get to know some insightful stories about their life, their past and their approach to love. 

35. ‘What is a tattoo you have always wanted?’

The tattoos we get are usually of things or objects or people that hold significance for us. This is a subtle way of looking deeper into the story behind the ink dream. Ask your crush what they want to get inked on themselves in order to know what they are truly passionate about. 

FAQs

1. How do you keep a conversation going with your crush over text?

By asking lots of questions. You must be careful because you do not want to seem intrusive. Further, your responses to all the answers should also be engaging. You can tell stories about yourself on the same topic as a response too. 

2. How do you flirt over text?

By using flirty emojis and suggesting flirty themes of conversation. Some of them could be about sexual encounters, sending kiss emojis and the like. 

3. How do I make my crush blush over text?

By being kind to them, complimenting them and showing them that you care about what they tell you. Making your crush blush over text is about using the right emojis and flirting techniques!

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