150 Questions to Ask a Guy You Like (over Text / in RL)

Last Updated on February 20, 2021 by Michele Tripple

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Worried about striking up a conversation with that “one guy”? These questions to ask a guy can help break the ice!

Questions to Ask a Guy

Let’s talk about conversations. I’m talking about real, deep, connecting conversations. Starting a conversation with someone isn’t that hard, even if it’s someone you really like. It’s continuing that can be a challenge, especially when you are lacking in ideas of what to talk about. Be sure to check out our conversation starters over text as this is a pretty typical way for conversations to begin.

Half the problem is that we just don’t know what questions to ask! We’re here to help  with some really great questions to ask any guy to learn more about him and to keep the conversation going so that you can really get to know him!

How to talk to a guy

Before you set out to have that perfect conversation, remember that true conversations require a good amount of give and take. So don’t just pounce on him with a million questions and expect him to answer them one after the other. These questions are a great way to get to know him, sure, but they are also meant to help the conversation flow. If the conversation is flowing, then let it flow! 

Don’t be surprised when he wants you to answer questions back. So here’s a tip: don’t ask him any questions that you wouldn’t be willing to answer yourself!

Most importantly, relax and be yourself! You can’t expect every single conversation to be perfect, but these questions could help get the ball rolling.

Of course, we have a really great list of questions to ask a girl too for you to check out! 

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Reminder: Did you use these questions to talk to a guy you like? Did they help you keep talking? Share your favorite question on Instagram stories and tag me @micheletripple! I want to know which one you liked the best! I can’t wait to see what you are using to keep the conversation flowing!

Flirty questions to ask a guy

There’s nothing wrong with a little bit of flirtation. Flirting can let a guy know that you’re interested without putting yourself out there too much. These questions are sure to start some conversations and help you get to know him too!

  • What do you look for in a girl?
  • What is the perfect date?
  • What is the most romantic thing you have ever done?
  • What is the best first date?
  • When was the last time you had butterflies in your stomach?
  • What gift would make you fall instantly in love with someone?
  • How long does it take in a relationship for you to let down your guard?
  • Do your friends’ opinions influence your relationships?
  • If we spent a whole day together, what would we do?
  • Do you see me in your future?
  • How do you like to relax after a long day?
  • What are you most passionate about?
  • What two words would you use to describe yourself?
  • What is the best way to ask someone out?
  • What do you feel is your best feature?
  • What do you think my best feature is?
  • Do you prefer a night out or a night in?
  • Are you ticklish?
  • Who is your celebrity crush?
  • Are you sentimental? If so, about what?
  • What is the most romantic date you’ve ever been on?
  • How realistic do you think reality TV relationships are?
  • What is “love” to you?
  • Who do you think should make the first move, the guy or the girl?
  • What was your first impression of me?

Deep questions to ask a guy

Who doesn’t love a good thought-provoking question? These questions are sure to require some thought, from you and from him. Deep questions are a great way to see what is really going on inside that special someone’s brain.

  • What is the best piece of advice anyone ever gave you?
  • What’s something you learned this week?
  • When are you at your happiest?
  • When you are stressed, what helps you to relax?
  • What is one world problem you would fix if you could?
  • If you only had a month to live, what things would you do with your time?
  • What is something that you secretly wish you were amazing at?
  • What does it mean to you to be a good person?
  • Are you an optimist, pessimist, or a realist?
  • What are you most grateful for?
  • What do you like most about yourself?
  • If you could live to be 100 and you had to choose between having the mind of a 30-year-old or the body of a 30-year-old your whole life, which would you choose?
  • If you could change one thing about human nature, what would it be?
  • If you could choose to live during any time in history, when would you choose?
  • What is your happiest memory?
  • When was the last time you cried? Why did you cry?
  • If you could give your past self one piece of advice, what would it be?
  • When you were a child, what did you want to do with your life? How have those dreams changed?
  • What areas in your life do you feel you need to do the most improving?
  • Do you believe people are inherently good or inherently bad?
  • If you could change one thing about your past, what would you change?
  • Do you forgive and forget? Or do you forgive and never forget?
  • How is your life right now different than what you thought it would be?
  • Who are the three most important people in your life currently?
  • What are some lessons you have learned the hard way?

Funny questions to ask a guy

Humor is one of the best parts of close relationships. We all need a laugh every now and again and these questions are sure to bring about some laughter. Don’t be afraid to join in on answering some of these questions yourself – remember, a good conversation requires give and take!

  • What is the weirdest thing you’ve ever said to a stranger?
  • What song can you not help but sing along to when it comes on?
  • What is the best pick-up line you’ve ever heard?
  • What is the best prank you have ever pulled on someone?
  • Who is famous that shouldn’t be?
  • Do you believe in any conspiracy theories? If so, which ones?
  • If you could choose to be a girl for a day, would you?
  • What is your favorite dance move?
  • What is the most pointless superpower?
  • How do you deal with people that you don’t like?
  • When was the last time you laughed so hard you cried? What was it about?
  • Do you sing in the shower?
  • What is one movie that you love that you are embarrassed about?
  • What is something that bothers you that probably shouldn’t?
  • When you replace the toilet paper roll, do you set the flap over or under?
  • What is the funniest memory you have?
  • If you became President, what would be the first thing you would do?
  • What song could be the theme song for your life?
  • Are you superstitious? What about?
  • If you could read people’s minds, what do you think they would say about you?
  • What was the worst job you ever had?
  • What is the funniest joke you can think of right now?
  • If you were a rapper, what would you call yourself?
  • What is the worst thing you have ever smelled?
  • What is the most useless object in the world?

Random questions to ask a guy

Now here’s a list of questions that you probably wouldn’t think to ask. They are some of the most random questions we could think of, but they are sure to lead to some really interesting conversations with a guy.

  • If you could have one superpower, what would it be?
  • What is something that makes you way happier than it should?
  • What is the weirdest thing you’ve ever put on a pizza?
  • Would you rather have no teeth or no fingernails?
  • If you could choose to spend the day with one celebrity, who would you choose? What would you do?
  • What is your dream vacation?
  • If you were in the witness protection program, what would you change your name to and where would you go?
  • What is your favorite place in the whole world?
  • What is your favorite drink?
  • If you could visit one place, where would you go?
  • Do you consider yourself lucky?
  • If you could choose any music group to join (past or present) who would you join and why?
  • What is your greatest fear?
  • After you have an argument, do you ever think about what you should have said later?
  • Could you survive in the wilderness for a month?
  • What is your favorite movie?
  • If you could read other peoples’ minds, would you want to?
  • What is your idea of fun?
  • What would you do if you were invisible for a day?
  • Who is the smartest person you know?
  • If you could live in any fictional book, what book would you choose?
  • Who is your greatest role model?
  • Are you afraid of heights?
  • Would you rather be able to speak every language or speak to animals?
  • What is one food item that you always try to keep around?

Interesting questions to ask a guy

These questions may have some interesting answers and they are sure to teach you a lot about him. Not only that, but it’s not hard to continue a conversation when you have these questions on hand.

  • If you could be the best at anything, what would you want to be the best at?
  • What would the world be like if everyone was like you?
  • If you could leave everything and everyone and start over somewhere new, would you?
  • If you could have a $500 gift card to any store, which would you choose?
  • What would be the WORST store to have a $500 gift card to?
  • What language do you wish you could speak?
  • What is the most impressive thing you know how to do?
  • What is the ugliest car you have ever seen?
  • Do you consider yourself to be polite?
  • Do you prefer to plan things or do you prefer spontaneity?
  • What kinds of rules do you put on yourself?
  • Are you afraid of growing old?
  • Do you believe in soul mates?
  • What job doesn’t exist but you think should?
  • What are some songs that you know all the words to?
  • What animal do you most identify with?
  • If you could start a business, what kind of business would it be?
  • What villain do you feel bad for?
  • If police raided your house right now, what would be the most incriminating thing they would find?
  • What is the perfect backyard like?
  • What first world problem do you often experience?
  • What is the worst song in existence?
  • What is the most important thing that you own?
  • What is the worst thing someone can major in in college?
  • What event in your life do you think would make a good movie?

Questions to ask a guy over text

During the times when you’re apart, it might be fun to occasionally ask him questions over text. Don’t overdo it though. No guy wants to receive 15 text messages a day of just endless questions.

  • If you had to choose only two foods to eat for the rest of your life, what would they be?
  • What is your favorite YouTube video? Can you send it to me?
  • What song do you listen to the most?
  • What is your favorite meme?
  • You have a choice between going cage diving with Great White Sharks or skydiving – which would you do?
  • What is your favorite movie quote?
  • What is the funniest picture you have on your phone?
  • How many phones have you gone through in the past two years?
  • What gif always makes you laugh?
  • What is your favorite restaurant?
  • What is an unpopular opinion that you have?
  • What is the best joke that you know?
  • What is the weirdest text you’ve ever gotten?
  • What’s the best photo you have on your phone right now?
  • What is the most embarrassing text you accidentally sent someone?
  • If you could buy anything right now, what would you buy?
  • What is something that isn’t real that you wish was?
  • What is something that you hate that most people love?
  • What phone app do you waste the most time on?
  • What is the funniest accidental call or text you ever received?
  • What is the background on your phone?
  • Which of your five senses would you give up if you were forced to choose one?
  • What is the first thing you would buy if you won a million dollars?
  • What is one movie you could watch over and over again?
  • What is something you would not do for all the money in the world?

Weird questions to ask a guy

Just like the random questions were random, these questions are definitely weird. Weird as they may be, you might be surprised at how much you can learn about someone from these questions.

  • What food do you think is overrated?
  • What are some random facts that you have memorized that you will probably never forget?
  • What fictional character do you have a crush on?
  • What is one fact that you wish you could unlearn? 
  • If you could only watch three movies for the rest of your life, what movies would you choose?
  • Does your brain ever go on autopilot?
  • How has your hometown changed since you were a kid?
  • What is something you’re glad you did once, but you would never do again?
  • If you could have any piece of tech, what would it do?
  • What is something that you have done a lot, but are still bad at?
  • What is your worst nightmare?
  • Is there a scene from a movie that you can’t unsee?
  • What is the most boring thing in the world?
  • What is the highest number of consecutive hours that you’ve spent awake?
  • What board game never ends well?
  • When was a time when the phrase “looks can be deceiving” really apply?
  • What is your favorite activity as a kid that kids don’t really play anymore today?
  • What is your favorite “go-to” meal?
  • If you could replace any part of your body with a robotic version, which body part would you choose?
  • If you had to choose one actress to marry right now, who would it be?
  • Do you like any cartoons?
  • What is something that you think other people say about you?
  • Have you ever been in a fistfight?
  • Can you juggle?
  • Do you have a nickname? How did you get it?
  • What is your dream job?
  • Who would play you in a movie about your life?

Important questions to ask a guy

These are some of those important questions to ask a guy that you really want to know! These help you learn so much about him like his dreams, hopes, motivation, and really in-depth things to decide if you want to pursue getting to know him more! 

  • Trying to figure out if you like a guy? There are some important questions to ask a guy to help you decide!
  • What is the next major goal you hope to accomplish?
  • What is the best purchase you’ve ever made? Why?
  • What are two things you are passionate about?
  • Are you an introvert or an extravert?
  • What is the biggest “deal-breaker” in a relationship?
  • What is the most annoying thing you’ve seen couples do in public?
  • What makes you the angriest?
  • Do you think you would make a good parent someday?
  • Do you like to read? What are your favorite books?
  • How open are you to talking about your feelings?
  • Are you a dog or a cat person?
  • Would you rather have a big house and be in debt, or have a small house and have money saved?
  • What do you hope to accomplish with your education?
  • How important is saving for the future (retirement, life insurance, investing, etc.) to you?
  • What would be your dream job?
  • What do you love most about your life right now?
  • What is something you would change about your life?
  • If you could live anywhere in the world, where would you want to live?
  • How do you feel about traveling?
  • When you get upset, how do you react? 
  • How do you handle being offended?
  • Do you believe in standing up to bullies?
  • What is the most important thing in life? Why?
  • If you could have unlimited knowledge about one topic, what topic would you want it to be?
  • What is your idea of a perfect evening?

Relationship questions to ask a guy

Looking to see if you want your relationship to go to the next level? These questions will help you figure that out. It’s important for couples to talk about their relationship if they want it to go anywhere.

  • What is your view on marriage and children based on your family’s experience?
  • What personality trait do you find most attractive in someone you are looking to date?
  • What do you see when you picture your life in five years?
  • When do you feel the most loved?
  • What do you value most in a relationship?
  • What is your family like?
  • What do you find romantic?
  • What do you think is an appropriate age to get married?
  • What are your thoughts on long-distance relationships? Could you handle it?
  • Do you want to have kids someday?
  • What do you think about Valentine’s Day?
  • What does your dream wedding look like?
  • What is more important to you: money or love?
  • How important is honesty in a relationship? Why?
  • How do you feel about a mom staying home with her kids instead of going to work?
  • Do you live your life based more on logic or more on emotion?
  • What do you see marriage being like in the future? 
  • How many children do you want?
  • What would you name your future children?
  • Where do you see yourself in 15 years? 
  • What would you think about your future wife having a very successful career where she earned more money than you?
  • What is your relationship with your siblings like?
  • How would you handle disagreements with your significant other?
  • How important are good looks to you in a relationship?
  • What is one thing you worry about most for your future marriage and family?

Awkward questions to ask a guy

My advice? Tread lightly on this category. You may need to wait until you know someone a little more before trying out any of these awkward questions. 

  • What is your most embarrassing moment?
  • What was your worst first date?
  • What was your weirdest breakup?
  • Who was your first girlfriend?
  • Describe your “dream girl.”
  • How many hours would you be awake in a day in a perfect world?
  • How long does it take you to get ready for a date?
  • If I wanted to give you a makeover would you let me?
  • If you held a world record, what would it most likely be for?
  • What is the last place on Earth you would want to live?
  • Would you describe yourself as frugal or frivolous?
  • If you could be inside any video game, which would you choose?
  • If you had to go back to school for one year, which grade would you go back to?
  • What do you like most about me?
  • How old do I look?
  • Have you ever stolen anything from a store?
  • Have you ever gotten a speeding ticket?
  • What is your most common food craving? 
  • Are you an emotional person?
  • Have you ever cried during a movie?
  • If you could be friends with any fictional character, who would it be?
  • What is one trait you look for in a significant other?
  • What is the meanest thing you have ever done?
  • What is the worst gift you ever received?
  • What’s the most ridiculous thing you’ve ever done to get a girl’s attention?

What questions would you add to the list? Share in the comments!

For more conversation starters, try these!

Questions to Ask a Girl 

Conversation Starters Over Text

Valentine’s Pick-up Lines

This-or-that Questions

Hilarious Would You Rather Questions

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