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300+ Questions To Ask A Guy Over Text

If you have recently started talking to a guy and are looking for interesting questions to ask him over text, this post will give you some awesome suggestions. Use the following list of questions to keep the conversation going while getting to know the guy.

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Questions To Ask A Guy Over Text

Questions To Ask A Guy Over Text

1. What is your biggest priority right now?

This question can help you figure out where the guy you’re talking to is in his life. You want to know what he is working on and where he focuses his energy. It is crucial if you are hoping to date him and want to see if he has the capacity to date you.

2. Which school experience has been the most rewarding for you?

Talking about school life can be a great way to keep an interesting conversation going over text. Find out what he learned from something good he experienced in school. His answer to this question will likely lead to others.

3. What is the next goal you want to accomplish

Knowing where the guy is in life is one thing and learning about the goals they have in mind is another. This can be a deep question to understand him better, but it can also allow you to talk about your goals and contribute to the conversation.

4. What career path do you see yourself taking?

If you are seriously considering dating this guy, you want to know as much about his life as possible, including his dream job. This open-ended question allows you to discuss different careers and what you both think of them. It could also open the door to discussing which college they would like to attend.

5. What is your idea of a spontaneous date?

Ask him about his spontaneous date ideas to keep the conversation light but fun. This will help you get some insights into his interests and see which of those match yours. It is also a great way of showing him that you’re open to dating without asking him out directly.

6. Have you been bullied before?

Bullying is common; unfortunately, it comes with undesirable effects as far as self-esteem goes. You might want to find out if the guy has gone through bullying in the past and what effects he has had to endure, not to pity him but to get a deeper understanding of him.

7. Sweet or salty, what do you like?

Before you go on that picnic date, ask what he prefers between sweet and salty snacks. This is a basic question but can bring up additional quarries on both ends, especially if you are planning a date together.

8. Is there a common reason why your relationships ended?

Asking profound questions might not be easy, but finding the answer to this question can be extremely important if you want to date him. He will likely ask you about your previous relationships, keeping the conversation lively and engaging.

9. Do you have pets?

Asking about pets can reveal so much about the guy you are texting to a great extent. You will learn about his sense of responsibility, love for animals, connection with his pet, and how he takes care of it. Generally, this will give you insights into the kind of person he is.

👍 You might also enjoy reading: Good Pets For Teens & Tweens

10. What is the most amazing dream you have had?

Dreams do not always come true and do not indicate a person’s current life, but they are an excellent way to break the ice if you just started texting a guy. From this question, others will come up, keeping the conversation light and engaging.

11. What is your favorite food?

There is always space to talk about food in any conversation. Ask the guy what he prefers to eat, whether that is at home or out in restaurants. Talk about your favorite food and sneak in a suggestion to try some food together sometime.

12. What are you most grateful for?

Get deeper into the conversation and ask about what he is most grateful for. This question will reveal the essential things in his life and give you an idea of what he values the most.

13. What kind of music do you like?

Everyone has their taste in music, and even though the guy’s type of music might not match yours, knowing what he likes can help you gauge where his interests are. Send him links to your playlists and ask for his playlist to compare notes and see what he likes.

14. What makes you happy?

You might want to understand what makes people happy if you are getting to know them. Again, this will reveal what matters most to them and where they direct most of their energy. You’ll also find out if you have interests in common.

15. What is the most embarrassing thing that has ever happened to you?

Talking about embarrassing stories turns a serious conversation into a light-hearted one and can help you create a deeper connection with a guy. If the guy is shy, they will be more comfortable talking about his embarrassing moments via text.

16. What is one skill you have that you are proud of?

Learning about a guy’s strengths is essential, especially if you want to create a long-term connection with him. Engage him by asking about his skills and the ones he is most proud of. 

17. What is your favorite memory of your childhood?

Childhood experiences significantly impact who we become, so learning about a guy’s childhood would be insightful. Talking about a favorite memory highlights certain aspects of his life and will take him back to his earlier days.

18. How do you relate to your parents?

This deep question can help you learn about a guy’s most important relationships, particularly with parents or guardians. If he is comfortable answering, he will have a lot to say, and the question will spark more to keep the conversation going.

19. Who is your role model?

You want to get insights into who inspires a guy and why they choose them to be their role model. Answers to this question can help you learn about his interests, hobbies, aspirations, future goals, and motivators.

20. How would you describe your personality?

There is no better way to understand someone’s personality than by asking them about it. Learning about the guy’s personality can help you understand why they do things the way they do them and why they are interested in some things and not others.

21. What is on your bucket list?

Ask the guy to share his bucket list with you, and be ready to share yours. You will learn what the other wants to do and where they want to go, maybe you could have something in common. It doesn’t have to match yours but will help you learn more about him.

22. What is the best gift someone has given you?

Where does he place his value as far as gifts go? Even if you know his interests, you might not know what to gift him when the time comes. The best gift he has received can help you understand the gifts he appreciates more than others and why.

23. What are your top pet peeves?

Pet peeves are a topic you want to have as early as possible, to understand what irks the guy you are talking to. Talk about yours, too, and make it an open conversation to share freely.

24. What do you do during your free time?

How does the guy spend his free time? Learning about his hobbies can draw you closer to a guy as you share yours. You might find some in common, and you could have unrelated hobbies, but at least you learn what the other likes most.

25. What is your top quality in a girl?

Every guy has a non-negotiable top quality they value in a girl they want to date. You want to learn about this as early as possible and take the opportunity to talk about your top quality in a guy. This question can help you gauge your compatibility in the early talking stages.

Watch the video below for some texting tips on how to keep a guy hooked:

Deep Questions To Ask A Guy Over Text

Deep Questions To Ask A Guy Over Text
  1. What is your least useful skill or talent?
  2. What makes you the happiest?
  3. What would you do if you spent your entire life doing one thing?
  4. Do you have food allergies or restrictions?
  5. What do you like the most about the way you look?
  6. What would you change about your life if you could?
  7. What is the most important characteristic you look for in a girl?
  8. What is your relationship with your best friend like?
  9. What have you learned recently that blew your mind?
  10. What is the most memorable trip you took, and why?
  11. What is the most painful experience you have gone through?
  12. Who do you look up to the most?
  13. Where do you get your motivation from?
  14. What have your past relationships taught you?
  15. What would you say to me if you had the freedom to say anything?
  16. If you could bring someone back to life, who would it be and why?
  17. What is your top affirmation to yourself?
  18. Which inspirational quote do you like the most?
  19. What are you most afraid of?
  20. Do you have a burning desire right now?
  21. If you could change something that happened in the past, what would that be?

You might also like to read 41 Answers To Questions Girls Are Afraid To Ask Guys

Flirty Questions to ask a guy over text

Flirty Questions To Ask A Guy Over Text
  1. How would you describe the perfect date?
  2. Why are you still single?
  3. What is the most romantic thing you have done for a girl?
  4. What do you think is your best physical feature?
  5. What do you fancy most about a girl’s body?
  6. How do you know you like someone?
  7. What makes you think someone you’re talking to is impressive?
  8. What do you find intriguing about a girl?
  9. Do you get drawn to looks or brains?
  10. Do you consider yourself a romantic person?
  11. What would your weekends look like if you were dating?
  12. How do you predict it would go if we went on a date?
  13. What are you looking forward to when you meet me?
  14. Do you feel comfortable talking to me?
  15. What are you obsessed about right now?
  16. What is a random thing that you find sexy in people?
  17. What was your first kiss like?
  18. What are some things you want to do with me the next time we meet?
  19. How do you like to express love to a girl you love?
  20. What is your top love language?
  21. What kind of clothes do you find the best on a girl?
  22. Hugs or holding hands, which ones do you like the most?
  23. If you could spend an entire day with me, what would it look like?
  24. What excites you the most about dating?
  25. What do you wear that makes you feel your best?
  26. Which is your favorite romantic song?

Here are some more Flirty Questions To Ask Your Crush (while texting!)

You can also watch the video below on some flirty texts guys will always respond to:

Funny Questions To Ask A Guy Over Text

Funny Questions To Ask A Guy Over Text
  1. What is the worst pickup line someone has ever used on you?
  2. What is the most embarrassing thing that happened to you recently?
  3. What did you want to become as a child?
  4. If you could have a secret video of someone, who would that be and why?
  5. Can you think of one funny thing that happened to you?
  6. What do you think mostly after waking up?
  7. What is a joke you find funny that other people don’t?
  8. How was your room as a child decorated?
  9. What song would you play as your soundtrack if you got into a fight?
  10. What is the funniest thing you have done to stay relevant?
  11. Have you had a wardrobe malfunction? What was it like?
  12. What is the most embarrassing thing you have done with your friends?
  13. What is a guilty pressure you hide from your friends?
  14. What do you like doing that everyone else hates?
  15. What is the worst pickup line you’ve used?
  16. Could you tell me what your ex would say about you?
  17. What is the one thing you cannot figure out about girls?
  18. Which piece of clothing would you pick if you wore girls’ clothes?
  19. What was the most embarrassing thing you did as a child?
  20. How would you describe the female version of yourself?
  21. What would you do if you woke up as a woman?
  22. What do you think is the weirdest way to meet someone?
  23. What is the lamest joke you know?

Juicy Questions To Ask A Guy Over Text

Juicy Questions To Ask A Guy Over Text
  1. Do you prefer blind dates?
  2. What physical traits do you fancy most in a girl?
  3. Would you make breakfast for the girl you love?
  4. What is your idea of a romantic date with your girl?
  5. Which quality of yours attracts a girl the most?
  6. What is one thing you wish everyone knew about you?
  7. What is one thing you would never want your parents to know about?
  8. What are you looking forward to the most once you start dating?
  9. What would you do if you spent an entire day on a deserted island with a girl?
  10. If everyone in the world followed your advice, what advice would you give?
  11. What advice would you give your girlfriend if they were having a bad day?
  12. What would the world look like if there were more people like you?
  13. What is the craziest thing you would do at your bachelor’s party?
  14. How do you judge a stranger?
  15. What do you find boring in people?
  16. What would you do if you were the only human on earth right now?
  17. What is the best compliment you have ever received?
  18. When was the last time you lied and said that you were okay while you were not?
  19. Who do you get on with the best in your family?
  20. What do you do in private that you wouldn’t want your friends to know?
  21. How was your first kiss experience?
  22. What do you hate doing but still do it all the time?
  23. If you could record two memories and keep them forever, which ones would you choose?

You might also like to read First Date Ideas For Teens

Awkward Questions To Ask A Guy Over Text

Awkward Questions To Ask A Guy Over Text
  1. What childish thing do you still enjoy doing?
  2. What is the lamest movie you have watched?
  3. Which game do you always lose when you play?
  4. What are you most terrible at?
  5. What do you hate to admit you like?
  6. Have you ever done anything unprofessional?
  7. What is a phobia that you have?
  8. When were you last caught lying?
  9. What is the most embarrassing thing you have done?
  10. When were you last confused about something?
  11. Have you had a crush on more than one girl simultaneously?
  12. What were you most afraid of in childhood?
  13. What about your future would you like to know?
  14. What are your thoughts on open relationships?
  15. Have you ever been on a diet?
  16. How much time do you spend on your phone?
  17. Do you have famous friends?
  18. How long do you take to shower?
  19. How long have you gone without a shower?
  20. What would you do if you walked into someone naked?
  21. Have you ever peed in a swimming pool?
  22. When did you last cry?
    ❤️ Have a look at these Emotional Love Letters For Him That Make Him Cry
  23. What is the most useless thing you have ever bought?

Interesting Questions To Ask A Guy Over Text

Interesting Questions To Ask A Guy Over Text
  1. What do you fantasize most about?
  2. Do you think karma exists?
  3. What do you think about religion?
  4. How will the world be 50 years from now?
  5. What is a major goal you have right now?
  6. Should guys and girls split the bill in a restaurant?
  7. What is the worst lie you have told someone?
  8. Is there anything you have done wrong in the past that you regret?
  9. What opinion do you have about marriage?
  10. Does physical attraction play a role in relationships?
  11. What is the most appropriate age gap in a relationship?
  12. Who has had the most significant impact on your life?
  13. Have you experienced true love before?
  14. Do you consider yourself romantic?
  15. Who do you talk to when feeling down?
  16. How would you describe me to your friends?
  17. What is one thing a woman should never do?
  18. Is love the most crucial thing in life?
  19. Do you have a celebrity crush?
  20. Do you have feminine traits?
  21. What is your favorite place to be on the weekends?
  22. Do you prefer the pool or a hot tub?
  23. What makes you fall for someone?
  24. What outdoor activities do you like?
  25. What compliments do you like to hear?

Personal Questions To Ask A Guy Over Text

Personal Questions To Ask A Guy Over Text
  1. What do you like most about yourself?
  2. What do you want to improve in yourself?
  3. What do you value the most?
  4. Who is your closest friend?
  5. What is your biggest weakness?
  6. What are you most fearful of?
  7. Do you have phobias?
  8. What is the best surprise you’ve gotten?
  9. Which video game would you play for life?
  10. What is your most precious possession?
  11. What is your favorite social media platform?
  12. What would you change about your childhood?
  13. When is your birthday?
  14. What do you want for your next birthday?
    ❤️ You might enjoy these Romantic Surprises for your Boyfriend’s Birthday
  15. When do you feel most heartbroken?
  16. Have you lost someone special?
  17. Do you read books?
  18. Which experience has had the most impact on your life?
  19. When were you last sad about something?
  20. Have you struggled with mental health in the past?
  21. At what age did you start dating?
  22. Have you sacrificed something for someone?
  23. What was your first relationship like?

Truth Questions To Ask A Guy Over Text

Truth Questions To Ask A Guy Over Text
  1. When was the last time you got furious?
  2. Have you ever flashed someone?
  3. Who do you regret kissing?
  4. What is the worst gift you have gotten?
  5. Have you ever stalked someone?
  6. Have you ever shared a toothbrush with someone?
  7. What would you do if I gave you $100?
  8. What is on your nightstand?
  9. Do you have a weird fetish?
  10. What is your favorite body part in a girl?
  11. Have you had a crush on an older girl?
  12. When was the last time you cried?
  13. Have you been cheated on before?
  14. What is your biggest insecurity?
  15. What have you gotten away with in the past?
  16. What name would you give your first child?
  17. What would I be shocked to find in your room?
  18. Do you have dirty pictures on your phone?
  19. Have you ever been stood up by a date?
  20. Have you skinny dipped?
  21. Has anyone seen you naked accidentally?
  22. What do you think of hickies?
  23. Do you dance by yourself?
  24. Do you sing in the shower?
  25. Have you been caught snooping on someone’s phone?

You might also like to read Truth Or Dare Questions For Teenagers (With Dares)

Good Questions To Ask A Guy Over Text

Good Questions To Ask A Guy Over Text
  1. What types of movies do you like to watch?
  2. Is watching sports more fun than playing them?
  3. How far would you go with a first date?
  4. Do you sleep with clothes on?
  5. Do you have any childhood dreams that have come true?
  6. How would your best friend describe you?
  7. What do you wish no one knew about you?
  8. What is the best quality a person can have?
  9. What would you like to become when you grow old?
  10. What does your retirement look like?
  11. Where would you want to live with your family?
  12. Would you relive your life if given a chance?
  13. What impresses you the most about people?
  14. Which animal would you want to be?
  15. What would you tell someone having a bad day?
  16. What is your favorite part of your day?
  17. What are your thoughts on social media?
  18. What do you do after a long day?
  19. What does a relaxing weekend look like for you?
  20. What do you value most in people you are close to?
  21. What do you do for self-care?
  22. What is one thing that could easily ruin your day?
  23. Who do you wish you had more time for?
  24. Have you broken someone’s heart before?

Fun Questions To Ask A Guy Friend Over Text

Fun Questions To Ask A Guy Friend Over Text
  1. What is your go-to video for laughs?
  2. Which song has the best intro?
  3. Which is your favorite movie of all time?
  4. Which joke do you say the most?
  5. What is your favorite quote?
  6. What would you do if you were a girl for a day?
  7. What do most people get wrong about you?
  8. What is your top guilty pleasure?
  9. What is the funniest pickup line you’ve heard?
  10. Who did you last try to impress?
  11. What do you wear when alone?
  12. Do you believe in love at first sight?
  13. How do you start small talk with strangers?
  14. What lesson about men would you teach girls?
  15. What kind of clothing looks best on a woman?
  16. Can girls and guys be friends without catching feelings?
  17. What would you do if you had a day with your crush?
  18. Have you been caught staring at a girl?
  19. What kind of compliments do you like to hear?
  20. What makes you smile the most?
  21. What do you like to drink often?
  22. What do you daydream about when bored?
  23. What is the craziest thing you have done to seek attention?
  24. What physical quality do you compliment people on?

Random Questions To Ask A Guy Over Text

Random Questions To Ask A Guy Over Text
  1. Who was the last person you called?
  2. Who do you talk to the most?
  3. What is your go-to dinner meal?
  4. What is the craziest thing you have done for a friend?
  5. Have you ever sent a love letter?
  6. What is the weirdest thing you have received in the mail?
  7. What is the one thing you would hire someone for?
  8. How far away would you live?
  9. Are you scared of commitment?
  10. What makes you trust someone?
  11. Have you ever cried in front of someone?
  12. What kind of father do you want to be to your kids in the future?
  13. What do you fear in romantic relationships?
  14. What would you never tell your crush?
  15. What bring you the most joy in life?
  16. What would you sacrifice life for?
  17. Money or love, what would you choose?
  18. What does a healthy relationship look like to you?
  19. Should people keep secrets in relationships?
  20. Could you forgive someone that cheated on you?
  21. Guess what I am wearing right now?

Intimate Questions To Ask A Guy Over Text

Intimate Questions To Ask A Guy Over Text
  1. What is the most sensitive part of your body?
  2. What is your idea of a perfect girlfriend?
  3. What is the one thing that turns you off the most?
  4. Do you have secret fantasies?
  5. What is your ideal first date?
  6. When are you most comfortable talking?
  7. Do you like it when a girl makes the first move?
  8. Have you felt butterflies in your stomach before?
  9. Do you prefer flirty texts or face-to-face chats?
  10. What do you like in a girl but are shy to admit?
  11. When do you think girls look most beautiful?
  12. How do you express love?
  13. What do you do when angry?
  14. Are birthdays special to you?
  15. Which scent do you like on a woman?
  16. What is your favorite memory of us?
  17. What reveals a person’s character most when dating?
  18. How would you know if someone was the right person for you?
  19. What would you undo from the past if given a chance?