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300+ Questions to ask a guy you like and bond deeper with him

300+ Questions to ask a guy you like and bond deeper with him

Updated on Oct 12, 2022

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

300+ Questions to Ask a Guy You Like and Bond Deeper with Him

Are you looking for a list of questions to ask a guy you like? Worry no more. You’ve landed just the right place.

Whether you are with your friends or spending some time alone with the guy, these fun questions will keep him engaged all throughout.

Obviously, guys have different areas of interest than girls. So, you might enjoy talking about fashion or makeup; while your guy may be more interested in sports.

However, everyone prefers something funny, right? So, start the conversation by discussing something funny with your guy to grab his attention.

300+ Questions to Ask a Guy You Like and Bond Deeper with Him
300+ Questions to Ask a Guy You Like and Bond Deeper with Him

Funny Questions to ask a guy you like

After a day’s work, nobody wants to talk to anyone likely to bring more stress.

So, act as a stress buster for your guy with our following list of some fun questions to ask a guy you like and keep the conversations flowing.

  1. What is the most hilarious incident in school?
  2. What are the funniest things on your bucket lists?
  3. What was your childhood nickname?
  4. Can you guess my childhood nickname?
  5. What is one incident you will never forget for the rest of your life?
  6. Which is the one dish you can eat as food for the rest of your life?
  7. Water or pizza, what will you choose?
  8. Have you ever been scared of something random?
  9. What is the theme song for your life?
  10. What is your weirdest kitchen fail?
  11. Have you ever fallen down on stage?
  12. Can you describe the best yoghurt topping ever?
  13. What do you still do that you are probably too old for?
  14. Which musical event would you love to be a part of?
  15. Have you ever been caught cheating on an exam?

By now, you would be laughing and sharing stories already.

So, when the mood is all set, why don’t you start with some…

Flirty questions to ask a guy you like

How difficult is it to strike a flirty conversation with someone you like? Well, it might make you go all sweaty and panicky to hit the first chord.

But with this list of flirty questions, I assure you that you are going to spend some memorable time with each other.

Brownie points for that cute smile on your guy’s face! 😉

  1. Would you like to have me for dessert?
  2. Have you ever sent someone flirty texts?
  3. Do you like it when the girl makes the first move?
  4. Would you want to spend a day at the beach with your girl?
  5. Which is your favorite cheesiest pickup line?
  6. What turns you on?
  7. Do you enjoy hugs?
  8. Do you enjoy cuddling?
  9. Do you think a healthy relationship requires mental and physical compatibility?
  10. Which romantic movie would you like to see with your girlfriend?
  11. What is your idea of an at-home perfect date night?
  12. What do I do that brings a smile to your face?
  13. When was your first kiss?
  14. Have you ever played a game of strip poker?
  15. What does a girl do that makes you feel secure?

I know you don’t want to sound too desperate being a girl and hence, would want to change the topic soon after giving him some hints.

To get a breather, you can certainly delve deep with…

Good questions to ask a guy you like

There will be certain things that you will want to know about the guy you like.

Hit up these questions to start a conversation and discover if they turn out to be exactly how you imagined.

  1. How will you describe yourself in five words?
  2. Your favorite female fictional character?
  3. Who is your favorite male movie character?
  4. Which family member are you the closest with?
  5. What is the biggest accomplishment of your life?
  6. What song can you listen to for a full 24-hour day?
  7. Who is your celebrity crush?
  8. What is a family tradition that you absolutely love?
  9. What is your dream job?
  10. Where do you see yourself in the next five years?
  11. How often do you take out time to travel?
  12. What is a topic you can’t stop talking about?
  13. Will you call yourself a procrastinator?
  14. What is the worst movie you’ve ever seen?
  15. Are you a beach or a mountain person?

These questions will help you understand if you are compatible with each other.

After this, you can jump on to some…

Deep questions to ask a guy you like

By now, you definitely know the person… but only on a superficial level. It is now time to dig a little deeper within the layers of his personality to find out who he really is.

Guys are extremely good at hiding their vulnerabilities but if he unveils them in front of you, congratulations… he is falling for you too!

  1. How do you take a break from all the stress?
  2. What is your spirit animal?
  3. Do you think asking for forgiveness is easy?
  4. Who is your dream girl?
  5. Will you call yourself religious or spiritual?
  6. How often do you cry?
  7. Do you believe in therapy?
  8. What is the best advice your parents gave you?
  9. How much money do you think is enough?
  10. When did your life take the biggest turn for the better?
  11. Have you ever lost someone close to you?
  12. Which qualities do you admire the most in your friends?
  13. What is your favorite happy memory?
  14. Which random act of kindness was you a part of?
  15. Do you think being rich means being happy?

Enough of deep talks…. Time for some weirdness! 😉

Weird Questions to ask a guy you like

Grab a corner, some packets of chips to eat and shoot these questions that may or may not have a logical meaning. But they are certain to help you know your guy’s crazy side.

So, just play it like the 21 questions game and relish that confused look on his face while answering the questions.

  1. Do you ever feel the urge to dismantle a technological gadget?
  2. If you could only eat one food from your favorite restaurant, what would it be?
  3. Have you ever stalked someone on social media?
  4. How many pillows do you sleep with?
  5. Would you ever sneak into your girlfriend’s phone?
  6. Which gross thing do people do which pisses you off?
  7. Have you ever puked in a public place?
  8. Should toilet paper be hung over or under?
  9. Do you have a fast-food horror story?
  10. What is the best funeral you can imagine?
  11. What piece of tech would you want to be an inventor of?
  12. What old-fashioned thing do you still do?
  13. Which part of your body would you replace with a mechanical version?
  14. What is the weirdest joke you can think of?
  15. Have you ever been slapped in public?

Once you have shown your weird side, it is now time to show that if time demands, you can also be a sane individual with a rational thought process.

Mature questions to ask a guy you like

To plan a future together requires a lot of planning. And you can only plan things when you have some information about the guy you like.

So, it’s time to show that you are serious about your life plans and you know how to behave like mature adults before making an impulsive decision.

Ask these mature questions to know more about your guy.

  1. Do you think breaking the ice is important in a conversation?
  2. What is the one app on your phone you can’t stay without for a long time?
  3. Are you afraid of old age? Why or why not?
  4. What do you think is an important part of two people to connect on a deeper level?
  5. Have you ever been involved in cyberbullying?
  6. Do you think of yourself as an introvert or extrovert?
  7. What do you like the most about your best friends?
  8. How often do you spend time with your family?
  9. Which year would you travel back to, if given a chance?
  10. What advice would you give to your teen self?
  11. What was your worst phase in life?
  12. What has been your best day ever?
  13. Would you be willing to relocate once you fall in love?
  14. Have you ever seen your parents cry?
  15. Do you think second chances are worth a shot?

Now that you have started delving deeper into him, you can definitely make the conversation more interesting with some…

Personal questions to ask a guy you like

Oh yes! We know you were waiting for this list to pop up. In fact, these are the questions that you’ve wanted to ask him right from the beginning.

But you are nervous about it. Well, you should be.

You cannot directly ask a person about their personal life. They may feel offended and insecure. And that would be the last thing you would want a guy you like to feel.

So, wait for the right time.

Once you have reached a mutual ground of comfort… These questions will naturally find their way into your conversation.

  1. Have you ever done something illegal?
  2. Tell me some of your pet peeves?
  3. What is your biggest insecurity?
  4. Which is the one thing in your life that you are proud of?
  5. If given a chance, which family tradition will you want to change and why?
  6. Have you ever been bullied?
  7. Do you have any hidden talents?
  8. What are your thoughts on racism?
  9. Have you ever cheated on someone?
  10. Do you believe in happily ever after?
  11. What are you very passionate about?
  12. Who is your role model in life?
  13. What is your biggest regret in life?
  14. What are your beliefs about long-term relationships?
  15. What are you most afraid of in life?

And then some…

Psychological questions to ask a guy you like

Knowing his mindset is important. It helps you decide if your life ethos matches with his.

The below questions are perfect for you to decide if he is an ideal fit for your core values.

  1. Which parent are you closer to and why?
  2. What can never make you angry?
  3. Will you ever change your career and why?
  4. Have you ever asked for a favor and regretted it?
  5. How often have you pretended to be someone you aren’t?
  6. What do you really get paranoid about?
  7. What can make you feel comfortable instantly?
  8. Do you often overthink?
  9. Do you miss school often?
  10. Are you still on good terms with your college best friends?
  11. What would you title a book about your family?
  12. Where would you go on your bachelor trip?
  13. Where do you think you deserve to go: heaven or hell?
  14. Is money more important or is happiness?
  15. Is there such a thing called soulmates?

Enough of serious discussions! Let’s lighten the tone now with some…

Embarrassing Questions to ask a guy you like

A conversation without digging into embarrassing stories… No, absolutely not!

I don’t want you to be devoid of this ultimate fun! 😉

So, go get some popcorn… while you can’t stop laughing at all his embarrassing stories.

P.S. Don’t judge him!

  1. Are you sure you aren’t gay?
  2. Have you ever explored your sexuality in a unique way?
  3. How many girl’s numbers do you have?
  4. Have you ever been caught watching porn?
  5. How much debt are you in?
  6. Do you think I need plastic surgery?
  7. Have you ever wanted to date older women?
  8. Have you ever been to jail?
  9. How would you kill someone if given the chance?
  10. Do you ever want to get married?
  11. Have you ever lied to your family to be with someone?
  12. Have you ever found someone younger than you hot?
  13. Have you ever dozed off in the washroom?
  14. Have you ever forgotten to reply to someone at work?
  15. Have you ever had a beer belly?

I see that you are already spending some fun moments with him.

Don’t you want to give him some more hints with…

Fun Flirty Questions to ask a guy you like

Flirting always gives butterflies. You neither want to sound desperate nor disinterested in the person you like.

So, here is the set of questions that will take you through the middle-ground while you continue having fun.

  1. Do you have a secret fantasy?
  2. What does your perfect day with your future girlfriend look like?
  3. Does online dating make sense to you?
  4. What is the deal breaker for you on a date?
  5. What is your favorite movie in bed?
  6. What is your favorite dare in a game of dirty truth and dare?
  7. If you had x-ray vision, who would you check out first?
  8. What is your type in women?
  9. Have you ever showered with a girl?
  10. How many girls have you been with till now?
  11. Do you like it when a woman is in yoga pants?
  12. How do you like to relax with your woman?
  13. Are you an old-school romantic?
  14. Have you ever been caught while making out in a public place?
  15. Do you enjoy a quickie?

Take the conversation forward with some…

Sexual questions to ask a guy you like

You explored his personality and mindset. If you have matched on those levels, it is now time to test your sexual compatibility.

I know it is tricky.

But the following list of questions is enough to keep you covered. Thank me later! 😉

  1. Which is your favorite body part of a woman?
  2. How do you like a woman to touch you?
  3. Have you ever ripped a girl’s clothes off in bed?
  4. What drives you crazy in bed?
  5. Do you want to know what color underwear I wear to bed?
  6. Would you ever be willing to try edible underwear?
  7. How many times do you do yourself in a week?
  8. How many times have you done it in one go?
  9. Do you think you can give good orgasms to your girl?
  10. What is your favorite type of lingerie?
  11. Do you want to see me in sexy swimwear?
  12. What taste do you love on a lady’s lips?
  13. Do you like it when she pulls your hair?
  14. Have you ever had a wet dream?
  15. How many days can you go without doing it?

Now that the conversation is already in a heated mode, keep it flowing with some…

Dating Questions to ask a guy you like

You obviously want to know his definition of romance to avoid any kind of disappointments in the future. These kinds of questions can also help you know how to surprise him and win his heart.

Yes, I can already sense your excitement… So let’s straight dive into the list.

  1. Which show did you binge-watch last?
  2. What is your go-to date idea?
  3. Would you go camping or clubbing?
  4. What is your go-to Starbucks order?
  5. Do you believe in love at first sight?
  6. In a relationship, what is more important: trust or respect?
  7. What would you gift your girl: flowers or chocolates?
  8. Would you ever compromise your career for a relationship?
  9. How do you deal with fights in a relationship?
  10. Do you prefer going to work early to leaving early?
  11. Would you ever date your boss?
  12. Have you ever said no to a girl even though you wanted to say yes?
  13. What is your guilty secret?
  14. Have you ever not paid for a date?
  15. Have you ever been to a photo booth with someone?

Aren’t you in love with him already? I know you cannot resist now and so, it’s time for him to admire your cuteness with some…

Cute Questions to ask a guy you like

You already have enough reasons to admire him. But if you want more, these questions are going to be your light of the day.

  1. Which song would you choose to sing on a karaoke night?
  2. Do you like to walk your woman up to the door?
  3. Have you ever played a prank on someone?
  4. Do ‘puppy dog eyes’ work on you?
  5. What would you call charming in a woman?
  6. Would you want to follow me on Instagram?
  7. What is your favorite comment ever on your Instagram account?
  8. What do you love to do to make someone smile?
  9. Are you ticklish?
  10. Would you ever share your food with someone?
  11. Do you like playing around with kids?
  12. When did you last goof up at work?
  13. Do you like those warm moments before hard goodbyes?
  14. Which new skill would you want to try with your partner?
  15. What is your most prized life lesson?

It’s time to control your emotions a little. So, let’s reroute the conversation with some serious digging.

Truth questions to ask

There are some things that you must know about a guy you like before taking a step forward.

You may ask him about his habits, his ambitions, fears, or anything that you feel you have missed out. Such questions help you understand if you want the same things from life.

  1. Would you give up coffee or alcohol?
  2. Do you smoke?
  3. How often do you lie?
  4. What is the most useful skill you ever acquired?
  5. What is the most ridiculous conversation you’ve ever had?
  6. What was your favorite family holiday?
  7. Do you believe in ghosts?
  8. Would you ever choose to be a President of a nation for one day?
  9. What makes you feel sentimental?
  10. Do you think crying is a sign of weakness?
  11. When did you last have a fight with someone?
  12. Why do you think divorce rates are high?
  13. Have you ever slept naked on the beach?
  14. What did you take for granted in your relationships?
  15. What did you think was stupid until you gave it a try?

Umm… how can a conversation with your crush be fun if you haven’t talked dirty?

Dirty Questions to ask a guy you like

Let’s just all accept the fact: this section is the most desired.

Try to know if your guy can only make your heart churn or is good enough to give you a good time in bed too.

Start with these questions! 😉

  1. What is your favorite snack in bed?
  2. What is your favorite place to get massaged?
  3. Do you have a fetish?
  4. Have you ever had a one-night stand?
  5. What is the most random place that you’ve done it at?
  6. Have you ever done it in a car?
  7. What are your thoughts on the dirty talk?
  8. Have you ever been in friends with benefits relationship?
  9. Have you ever had a “moment” on a video call?
  10. What is your best experience while trying out a new sex position?
  11. What do you feel extremely passionate about?
  12. What is your favorite position?
  13. What physical features turn you on the most?
  14. When did you lose your virginity?
  15. Have you ever tried foreplay?

If you’re still reading, I’m sure things so far have worked well for you.

If you find your guy panicking to answer the questions further, you can ask some…

Best questions to ask

These questions are called the best questions for a reason. The reason behind this is they never fail with guys.

When you find your guy distracted or going off-topic, you can shoot up any of these questions to answer.

This list will never disappoint you or him.

  1. Which sport would you play at the Olympics?
  2. Have you ever given someone a piggyback ride?
  3. Greece for history or Budapest for parties?
  4. What do you like to wear the most?
  5. What is the oldest possession you own in your cupboard?
  6. How hard do you think it is to let go?
  7. What is your favorite breakfast to have at home?
  8. Which planet will you travel to if given the chance?
  9. Do you enjoy board games?
  10. What do you find absolutely irritating among couples?
  11. Do you believe in love marriages or arranged marriages?
  12. Do you enjoy eating cookie dough?
  13. Are you someone who believes in having a strict food diet?
  14. Which celebrity do you think you resemble the most?
  15. Which is your most-used emoji ever?

Once you have gained his attention with the best questions, you can ask whatever is in your mind or go for some…

Random Questions to ask a guy you like

It is not a compulsion to always ask something trendy. You can have casual, random conversations with the guy you like.

Some of the random questions that you can discuss when you have nothing else in mind are:

  1. What animal do you think you resemble the most?
  2. What is the one conversation topic that can lead to endless conversations with you?
  3. What is your favorite book to re-read all the time?
  4. Are you in favor of text messages or against them?
  5. What do you think is the most useless subject in school?
  6. Who is the worst villain ever?
  7. Are you an organized or disorganized person?
  8. Which weird food flavor combination do you love?
  9. What is the best Wi-Fi name you can think of?
  10. Are you a cat or a dog person?
  11. Which video game would you never want to be a part of?
  12. Do you pay for your own Netflix subscription?
  13. What do you get the most compliments for?
  14. What is one quote you always remember to live by?
  15. What is the most useless purchase you’ve ever made?

Once he is comfortable with answering these questions, you can go on with some…

Great questions to ask

This list has topics central to a guy’s interests – they can strike hour-long conversations on them and still be hooked to you.

After all, there are only a handful of guys who don’t like cars or gadgets.

  1. What are your secret obsessions?
  2. Which reality show do you love?
  3. Which is your favorite Sports car?
  4. What is the surprise you’ve ever received?
  5. Are you a saver or a spender?
  6. Who was the best teacher in your life?
  7. How often do you order food online?
  8. Have you ever taken cooking classes to impress someone?
  9. Which person can you talk to about anything and everything?
  10. Do people at work appreciate you?
  11. Have you ever written something?
  12. Do you think financial independence is important?
  13. How often do you read books?
  14. Are you a waffle or a pancake person?
  15. Do you like girls who wear makeup?

But what if you are talking to your guy on text? Will these questions help?

If not, I have compiled a separate list for that.

Questions to ask over text

Talking on text and face-to-face are two different things. So, I assume, you might need different questions for both situations too.

If you agree with me, then the following are a few questions to ask a guy over text.

  1. What did you find interesting about my profile?
  2. How would you define a typical weekend for yourself?
  3. What is the most important part of your daily routine you can never change?
  4. Which was the last concert you went to?
  5. What is the best way to spend money according to you?
  6. Have you ever gone on a blind date?
  7. Which dream city would you want to spend the rest of your life in?
  8. What is the most meaningful gift you’ve ever gifted to someone?
  9. What is your favorite food cuisine?
  10. Are you a morning person or a night owl?
  11. Which crime would you commit if given a chance and with no punishment?
  12. Which is your favorite season of the year?
  13. Have you ever started crying while laughing?
  14. What is your favorite meme of all time?
  15. If you could be a superhero, which one would you be?

No, no, no… The conversation doesn’t end here.

You still have some…

Interesting questions to ask over text

If you are looking for some interesting questions to ask a guy, take the entire list from here.

Trust me, you will have no regrets.

  1. What is your philosophy in life?
  2. Do you believe in confrontations?
  3. Are you friends with all your exes?
  4. What do you think toxicity means in a relationship?
  5. What do you wish you had more time for?
  6. Are you indecisive?
  7. What is the one word you absolutely hate?
  8. What is one thing you think is overhyped?
  9. Do you believe in destiny?
  10. What is your favorite amusement park theme?
  11. How often do you donate?
  12. What would you do if you won the lottery?
  13. Do you like surprises?
  14. Have you ever been on tv?
  15. Would you ever want to try to be a radio jockey?

These questions should be enough to keep up a conversation flowing with a guy you like.

So, does this mean it’s the end of this think-piece? Absolutely not!

Here are some bonus tips to strike an engaging conversation with a guy if you feel nervous at all.

5 Tips to Flatter the guy you like

If you are really interested in this guy, I’m sure he sometimes makes you all jittery and confused.

And so, I have some bonus tips for you that will help you grab his attention even in a room full of people.

So, let’s go!

1. Compliment him

Now, it is an absolute myth that only girls love compliments. Your man loves to hear them too… and absolutely deserves them.

You can give him some easy-peezy compliments like “You look smart!” or “I like your shirt”. This is enough to keep him thinking about you the entire day.

2. Allow him to take the steps for you

Every guy wants to be the hero for his girl. If you are able to keep this heroic spirit alive in him, I can guarantee he belongs only to you.

For this, you can do a simple trick. Seek his help in all your given tasks.

3. Ask for his opinion

It matters to him a lot. Asking for an opinion does not make you any less of an independent woman. But it certainly makes him feel that he is an important part of your life.

It shows him that you care for his feelings and thoughts.

4. Get closer to him

Obviously, if you like him, you have to give him some hints. This can be easily communicated by some body language tricks.

Hug him in front of others, hold his hands or just fix his collar. All these are signs that you are looking for something more with him.

5. Avoid talking about money

Well, we know money matters to everybody but talking about it with your guy can be a huge turn-off for him. It shows him that you are money-minded.

It can also make him think that if you are wanting to be with him only for money!

Over to you…

So, now you know how to keep a conversation going with a guy you like. You can take these questions as a reference and keep creating some of your own.

Ensure that your questions don’t make him uncomfortable. If at all you are stuck at some point, refer back to this list to dodge the awkward silences.

Also, don’t forget to use the bonus tips to attract him towards you quicker. Enjoy your time with him and I hope you create unforgettable memories together.