101+ Questions to Ask a Guy Over Text to Get to Know Him Deeper

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When we’re getting to know a new guy, there’s usually a ton of things we want to ask them about. Of course, we can also get flustered and have no idea what to ask them in the moment! Here are over 100 questions to ask a guy over text to get to know him a bit better.

Remember that these questions are serving suggestions. You can, of course, ask them exactly as they are, or you can rephrase them to suit your own personality.

Here are the questions you can ask:

  • What are three things you’re grateful for?
  • Is there a fictional character that you really relate to?
  • What’s something that you’ve been wanting to ask me, but haven’t yet? Be brave.
  • Is there a type of music that you absolutely hate? If so, why?
  • What was it about me that first captured your attention?
  • If you could do anything with me this weekend, what would it be?
  • What’s something that makes you happy every time it happens?
  • Are you afraid of anything? If so, what?
  • What’s one of the scariest things you’ve ever experienced?

  • If you could talk to anyone from history, who would it be?
  • What would you ask them?
  • Similarly, if you could sleep with anyone from history, who would it be?
  • What’s your favorite type of food?
  • Do you know how to cook well?
  • Do you have any pets? If so, which ones?
  • What are your favorite animals (other than pets)?
  • What’s the weirdest animal experience you ever had?
  • Do you believe in ghosts? Why or why not?
  • What was the most amazing dream you ever had?

  • Have you ever shared a dream with anyone?
  • What’s the best date you’ve ever been on? What made it so awesome?
  • Conversely, what’s the worst date you’ve ever had?
  • Tell me the most embarrassing thing that ever happened to you.
  • Do you like to read? If so, what are some of your favorite books?
  • If you were to write a book, what would it be about?
  • Do you read erotica? If so, what kind?
  • What’s the weirdest place you ever had sex?
  • How do you like to be touched?
  • Do you prefer to be gentle or rough in bed? (Or a bit of both?)

  • What’s a skill of yours that you’re particularly proud of?
  • Do you have any talents that aren’t common to most people?
  • What about hidden talents? Are you able to do some cool stuff, but don’t tell anyone about it?
  • Tell me about one of the best meals you ever had: What type of cuisine was it? Where did you eat it, and who were you with?
  • Is there any type of food you absolutely hate or refuse to eat?
  • What was the best concert/live music experience you ever attended?
  • If we could go anywhere together right now, where would you want to be?
  • What would you want to do when we got there?
  • Tell me about one of the most memorable trips you ever took?
  • What’s a weird food combination you really like?
  • If you could change the ending to a movie or book, which would it be? What would you change?

  • If you could live in a world that only exists in TV or film so far, which would it be?
  • What was one of your favorite films or TV shows when you were a kid?
  • Do you get along well with your family?
  • What’s something wonderful you learned from a family member, even if you don’t get along with them?
  • Do you have any role models? If so,who and why?
  • What about the opposite: are there any people you absolutely don’t want to be like? Why not?
  • Which traits do you appreciate most in a partner?
  • What trait do you like best about yourself?
  • Are you happy with the way you look, or would you prefer to look different?

  • If you could change one major thing about yourself, what would it be?
  • What do you like best about the way I look?
  • Do you find yourself drawn to a certain “type”, aesthetically? Or do you like variety?
  • What’s a fantasy you have? Is it something you’ve never done before?
  • Is there anything that you feel shy about?
  • What’s the hardest job you’ve ever done? What was so difficult about it?
  • What would your dream job be?
  • If you could spend the rest of your life doing whatever you want, what would you be doing?
  • Do you have any food allergies or food restrictions?
  • How about ethical food choices? Do you choose not to eat certain foods? If so, which ones and why?

  • Do you believe in astrology?
  • What sign are you? If you don’t know, want to find out together?
  • Do you have a favorite drink? (Alcoholic or otherwise)?
  • Do you do any drugs? If so, which ones? If not, why not?
  • How do you feel about festivals? Do you enjoy going to big ones? Small ones? None at all?
  • What is your least useful skill or talent? (Bonus points if it’s ridiculous)
  • Do you like to work out? What’s your favorite workout/exercise?
  • Which do you prefer: to watch sports? Or to play sports?
  • How about yoga or Tai Chi?
  • Do you like movies? If so, which genres do you like best?
  • Star Wars or Star Trek? Or neither?

  • Do you have a favorite celebrity? If so, which one and why?
  • In the same vein, did you used to like or respect a famous person, but now you don’t? What happened to change your opinion of them?
  • Do you have any hobbies?
  • Are you someone who likes/needs a lot of alone time? Or do you prefer company?
  • Is there anything that you’re looking forward to in the near future?
  • What is a social justice movement that you feel really strongly about?
  • Have you ever been to a protest? If so, which one(s)? If not, would you?
  • How many languages do you speak? Do you want to learn more of them?
  • Is there anything else you still want to learn how to do?
  • Do you like to play games for fun? If so, which ones?

  • Are you a fan of cosplaying? (Either just for fun, or in the bedroom…?)
  • Do you like to get dressed up for Halloween?
  • If you had the chance to be an extra in a movie, what kind of film would you want to be in?
  • Tell me something that always makes you smile?
  • What’s something that you miss? Would you want it back, if you could have it?
  • Is there anything that’s guaranteed to turn you on?
  • What about the opposite: what’s an immediate turn off for you?
  • Pineapple on pizza: yes or no?
  • What do you like best about being a man? How about what you dislike the most?
  • If you could be a woman for a day, would you be? What would you do with your time?

  • Do you have any weird quirks?
  • If you could have one superhero power, what would it be?
  • How about if you could be any animal for a day, what would it be?
  • If you woke up and found that you were the last person on earth, how would you feel? What would you do first?
  • Who do you think is one of the most interesting people alive today?
  • If you could meet that person, what would you ask them? What would you talk about?
  • What are the three top items on your bucket list?
  • How about desert island survival: what five things would you want with you?
  • What would you miss the most if it suddenly disappeared from the world?

  • What’s the best gift anyone has ever given you?
  • What’s something that you want to let go of: either an item you’ve been carrying around with you for a long time, or a negative emotion you’re ready to move on from?

Now you have some solid ideas about questions to ask a guy over text so you can get to know him better. Remember to keep the conversation going by responding to the questions he has for you in turn! Keep things playful and flirty, but don’t push him to answer things that might make him uncomfortable. He’ll open up to you more when he’s ready.


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