151 Questions to Ask a Guy to Get To Know Him Deeper 2024

If you’re wondering about questions to ask a guy to get to know him deeper, what to talk about with a guy over text, or what to ask a guy over text, you’ve come to the right place.

Here are the best random questions to ask guys over text ready for you to copy, paste, and send, or use in person.

Questions to Ask a Guy

Here are some excellent questions to ask a guy to get to know him over text or in person.

  1. What is something most people don’t know about you?
  2. What’s the most traumatic experience you have had?
  3. Do you have any relationship deal breakers?
  4. What’s your ideal way to be woken up in the morning?
  5. Would you consider yourself an introvert or extrovert?
  6. Who’s the person you go to when you need to talk to someone?
  7. What’s a sexual turn on for you?
  8. Do you usually stay friends with your exes?
  9. Do you believe in second chances?
  10. Do you have any secrets that nobody knows about?
  11. Do you like it cold or hot when you sleep?
  12. Do you think flirting is cheating?
  13. What is your go to snack?

Questions to Ask a Guy to Get To Know Him Deeper

Here are some questions to ask a guy to get to know him deeper over text.

  1. What weird smell do you like?
  2. Do people generally guess your age correctly?
  3. If you find someone’s phone in a cab, what would you do with it?
  4. Do you prefer red wine or white wine?
  5. What is the spiciest food you have ever eaten?
  6. How many hours per night do you sleep?
  7. What’s the craziest place you have hooked up?
  8. Do you remember your dreams?
  9. What toppings do you like on your pizza?
  10. Have you ever had a threesome?
  11. Are you into fitness?
  12. Are you a morning person or a night person?
  13. Name one thing you’re grateful for?

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Good Questions to Ask a Guy

Here are some questions to ask him over text.

  1. Who’s your favorite celebrity?
  2. How long do you spend on social media each day?
  3. Do you remember your first kiss?
  4. Do you believe in ghosts?
  5. What’s your favorite sexual position?
  6. Are you allergic to anything?
  7. Do you play cards?
  8. Are you a fan of cosplay in the bedroom?
  9. What’s your biggest turn on?
  10. What’s a sexual turn off for you?
  11. How many nights a week do you go out?
  12. Name one thing on your bucket list?
  13. Would you like to be famous?

Random Questions to Ask a Guy

  1. If you could sleep with any tv star, who would it be?
  2. Do you know how to cook?
  3. Do you have an pets?
  4. What’s your favorite flavor ice cream?
  5. Do you like porn?
  6. What’s your worst first date experience?
  7. Do you prefer to be gentle or rough in bed?
  8. What were you like in school?
  9. What’s your favorite restaurant?
  10. What’s the best concert you’ve been to?
  11. Do you like traveling?
  12. What is your favorite color? 
  13. What age did you lose your virginity?
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Interesting Questions to Ask a Guy

Here are some interesting questions to ask a guy over text or in person.

  1. What would your dream job be?
  2. Who’s your favorite movie star?
  3. What’s your biggest fear?
  4. If you could have any super power what would it be?
  5. What’s the most embarrassing thing that has ever happened to you?
  6. What is one of your habits?
  7. Have you been to Vegas?
  8. Are you a dog person or a cat person?
  9. Do you prefer lots of friends or a few close friends?
  10. Where’s the weirdest place you ever had sex?
  11. Do you have any hidden talents?
  12. Is there any food that totally grosses you out?

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Questions to Ask a Guy You Like

Here you will find some intriguing questions to ask a guy you like.

  1. What do you eat for breakfast?
  2. Do you play an instrument?
  3. What’s the best vacation you’ve ever been on?
  4. Who are your role models?
  5. What are 3 characteristics you look for in a girlfriend?
  6. Are you adventurous?
  7. In terms of dating, do you have a specific type?
  8. What is your zodiac sign?
  9. Are you into eating healthy?
  10. Do you like going to the movies?
  11. Have you ever tried yoga?
  12. Have you ever been in love?
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Questions to Ask a Guy Over Text

Here are some terrific questions to ask a guy over text.

  1. Do you like watching sports?
  2. Are you the type of person who needs alone time?
  3. Do you like to gamble?
  4. Do you prefer Spotify or Apple Music?
  5. If you could be a girl for the day, what would you do?
  6. What’s the best gift you’ve received?
  7. Who’s your favorite super hero?
  8. What was your best subject in school?
  9. What makes you angry?
  10. If you won the lottery, what’s the first thing you would do?
  11. Do you have a nickname?
  12. What is your proudest moment?

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Fun Questions to Ask a Guy

  1. Where do you see yourself in 5 years?
  2. What do you wear to bed?
  3. Do you prefer winter or summer?
  4. How would your friends describe you?
  5. What emoji do you use most?
  6. What’s your favorite Netflix series?
  7. Are you closer with your mom or dad?
  8. What do you think of online dating?
  9. Do you have a best friend?
  10. Do you get along better with guys or girls?
  11. What is your favorite song?
  12. Have you ever been cheated on?
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Deep Questions to Ask a Guy Over Text

Consider the below when looking for deep questions to ask a guy over text.

  1. Have you ever been in a fist fight?
  2. Do you believe in karma?
  3. What is your most prized possession?
  4. Do you have any pet peeves?
  5. What’s the scariest thing you’ve ever done?
  6. If you could live anywhere, where would it be?
  7. Do you believe in soul mates?
  8. What’s one thing you could not live without?
  9. Do you prefer bars or clubs?
  10. What is your favorite holiday?
  11. What’s your favorite pick up line?
  12. Do you have a best friend?
  13. What do you think of girl’s making the first move?

Serious Questions to Ask a Guy

  1. What’s something you haven’t tried yet would like to, in bed?
  2. What’s the worst job you ever had?
  3. What’s the strangest food you ever tried?
  4. How do you drink your coffee?
  5. Did you have pets growing up?
  6. Do you prefer Instagram or TikTok?
  7. Do you shower at night or in the morning?
  8. When in a relationship, do you prefer to give or receive massages?
  9. If you could change one thing about your appearance, what would it be?
  10. What drives you to succeed?
  11. What’s your go-to drink at a bar?
  12. Would you say you look better or worse than 10 years ago?
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Personal Questions to Ask a Guy

  1. How often do you go to the gym?
  2. What is your all-time favorite movie?
  3. If you could go back in time, what age would you go back to?
  4. When is the last time you cried?
  5. Do you see yourself married someday?
  6. Do you have any hobbies?
  7. Do you prefer the East Coast or the West Coast.
  8. When you were little, what did you want to be when you grew up?
  9. What kind of music do you listen to?
  10. When snacking do you prefer potato chips or candy?
  11. Do you like roller coasters?
  12. How many siblings do you have?
  13. Are you close with your family?

Best Questions to Ask a Guy

  1. Are you religious?
  2. When on vacation, do you prefer laying on the beach or sightseeing?
  3. Do you get along better with guys or girls?
  4. What’s your longest relationship?
  5. How important is money to you?
  6. Did you go to camp when you were a kid?
  7. Do you prefer paper books or audio books?
  8. Did you play any sports in school?
  9. How many languages do you speak?
  10. Are you into video games?
  11. Are you scared of snakes?
  12. Do you have any tattoos?
  13. What’s your favorite comfort food?

Frequently Asked Questions

What Are Some Good Questions to Ask a Boy?

Here are some questions to ask a boy over text.

  • What’s your favorite Netflix series?
  • Are you close with your family?
  • How would your friends describe you?
  • What’s a sexual turn on for you?
  • Do you believe in soul mates?
  • What is your favorite song?

What Are Some Relationship Questions to Ask a Guy?

  • Do you get along better with guys or girls?
  • What’s your go-to drink at a bar?
  • Are you close with your family?
  • How important is money to you?
  • When is the last time you cried?
  • What’s your favorite comfort food?

What Are Some Easy Questions to Ask a Guy?

  • How do you drink your coffee?
  • How many siblings do you have?
  • Are you a morning person or a night person?
  • How many languages do you speak?
  • What’s your favorite comfort food?
  • Are you closer with your mom or dad?

What to Talk About with a Guy over Text

Here you will find what to talk about with a guy over text when your bored.

  • Funny memes you’ve seen recently.
  • Weekend plans.
  • Recent hobbies.
  • Common interests.
  • How Your Day Was
  • Food

Conclusion

You should be all set with things to ask a guy over text, and questions to ask a guy to get to know him deeper. Listen actively and show genuine interest in his responses.

Share your own thoughts and experiences as well, creating an atmosphere of mutual connection. For more info check out this wonderful article by Harvard Business Review.

Matt Furman
Matt Furman

Hi, I’m Matt, the proud owner of Connection Copilot. I live in NYC and I’m passionate about all things dating. With a bachelor's degree in psychology, a professional coaching certification, and over 20 years of experience as a top tier dating coach, I've had the privilege of guiding and empowering thousands of individuals on their journey to meaningful connections.

I was born in New York and have never left. Having immersed myself in the fast-paced dating scene of New York City, learning as I go, I have gained much wisdom through experience. Consider me your trusted companion in your quest for love.