350 Questions to Ask a Guy Over Text [The Go-To Resource]

If you find yourself hesitating before reaching out to a guy with just the right blend of wit, charm, and depth through text, this playful guide is your new best friend.

I’ve compiled an epic list of questions that will help you navigate the nuances of textual chemistry with ease. Whether you’re looking to make him laugh, ponder, or blush, my carefully curated questions are your secret weapon for building a connection that could just be the beginning of something special.

Table of Contents

350 Questions to Ask a Guy Over Text:

Fun Questions to Ask a Guy Over Text

When you want to keep things light and enjoy each other’s virtual company, fun questions are your go-to. Toss these into your conversation to make him smile, laugh, and see the witty side of you. It’s all about adding that spark of joy to your text exchanges!

What’s the craziest thing you’ve ever tried?
What is the best joke you know?
What was the last funny movie you watched?
What’s the craziest thing you’ve ever eaten?
What is something really funny to you, but no one else seems to think so?
What’s the best prank you’ve ever pulled?
What was your most embarrassing moment?
What’s your most bizarre pet peeve?
Do you have any funny stories about nicknames you or your friends had when you were growing up?
What would be the funniest way an animal could communicate, completely different from how humans do it?
What was the strangest dream/nightmare you ever had?
When was the last time you had to make a situation funny?
What do you think is the funniest genre of music?
If animals could talk, which creature do you think could tell the best jokes?
Are there any funny quirks or habits that you possess or observe?
Is there a particular joke or line that always makes you laugh?
How do you usually react when something funny happens unexpectedly?
Have there been moments that were too funny not to laugh about, even if it was inappropriate?
What’s the most ridiculous way you’ve ever hurt yourself?
Is there anything unique about your personality or life story that people still laugh at when they hear it?
What’s the dumbest way you’ve been injured?
What’s the most useless talent you have?
Have you ever had a nickname? What’s the story behind it?
What’s the worst fashion trend you participated in?
If animals could talk, which would be the rudest?
Is there a movie you know so well that you could recite all the lines?
If you were a wrestler, what would be your entrance theme song?
Have you ever taken something from a hotel room?
Which would you rather fight: one horse-sized duck or a hundred duck-sized horses?
If you could instantly become an expert in something, what would it be?
What’s the strangest gift you’ve ever received?
Do you have any hidden talents?
If you could have dinner with any cartoon character, who would it be?
What’s your favorite meme?
What’s the silliest fear you have?
What’s the weirdest dream you’ve ever had?
What’s something that everyone looks stupid doing?
If you were a ghost, how would you haunt people?
What’s the most embarrassing thing you have ever worn?
What’s something you’re surprisingly bad at?
Have you ever been told you look like someone famous? Who was it?
What’s the weirdest conversation you’ve ever overheard?
How would you survive a zombie apocalypse?
What game are you absolutely terrible at?
What’s the worst haircut you ever had?
What would you do on Mars for fun?
If you could switch lives with one of your friends for a day, who would it be?
What’s the weirdest conversation you’ve ever overheard?
What sport would be the funniest to add a mandatory amount of alcohol to?
What’s the most ridiculous fact you know?

Flirty Questions to Ask a Guy Over Text

Flirty questions spark that electric feeling that comes with a crush. They’re like sending a wink and a smile across the digital void. Use these to tease out a blush or two and keep things interesting. And who knows, you might just find out if the feeling is mutual.

What’s a random fact about you that you think I’d find cute?
Do you think about me when we’re not texting?
What outfit of mine is your favorite?
Do you prefer long hugs or slow kisses?
What’s something you find incredibly attractive that you think I wouldn’t expect?
How would you describe your ideal date?
If I dared you to kiss me, would you be hesitant or adventurous?
What’s a feature of mine that caught your attention?
Do you believe in love at first text, or should I send another one?
What’s the most romantic thing you’ve ever done for someone?
Do you like it when someone makes the first move?
What’s the most flirtatious thing you’ve ever said or done?
If I were a dessert, what would I be and why?
What nickname would you give me based on our conversations?
How do you feel about holding hands in public?
What’s your favorite thing to do to someone you’re attracted to?
If you could describe our conversation in three words, what would they be?
What was your first impression of me?
If we were in the same place right now, what would you want to do?
What do you wear when you’re feeling the most confident?
Do you miss me as much as I miss you?
What do you think of when you think about me?
Is there a question you’re hoping I’ll ask you?
Do I make your heart skip a beat when I talk to you?
When was the last time my text made your day brighter than usual?
What little things do I do that make sure you know how much I care for you?
How do my smile and eyes captivate you the most when we’re together?
Is my presence enough to make your day better?
Is there anything that I do that warms your heart?
Do you prefer cute or hot selfies?
What is your favorite thing about spending time with me?
What kind of activities make the sparks fly between us when we are together?
How do we get closer even if we communicate through text messages?
How can I let you know how much my feelings for you grow every day without saying too much?
Is there something unique that we do together that no one else can understand the feeling behind it?
How do you feel when I smile at you and make eye contact?
Do you think this connection between us is going to last forever?
What kind of surprises do you enjoy receiving from me?
Do you get butterflies in your stomach when I smile at you?
How often have you found yourself daydreaming about us together?
Are there any old memories that make you blush whenever you think about them?
Do you still remember the exact moment when our eyes first met?
How about ditching the plans for tonight and streaming our favorite movie together?
When was the last time that just thinking about me made your day better than expected?
How often do you think about me when we’re not together?
Can you think of a reason to come over and see me?
If I asked nicely, would you do something for me?
On a scale of 1-10, how much do you like me right now?
Do you think about me as much as I think about you?
Do random thoughts about me ever cross your mind throughout the day?

Deep Questions to Ask a Guy Over Text

Sometimes, the mood calls for something a bit more thoughtful. Deep questions open up the floor for those long, meaningful chats that happen when the world’s quiet. They’re about getting to know the real him – what makes him tick and the dreams he’s chasing.

What makes you feel most alive?
What is the importance of family to you?
What is something that really scares you but also interests you?
What do you believe makes a successful relationship?
How have your experiences shaped the person you are today?
Do you have any irrational fears or superstitions?
Are there any life lessons that have had a particularly strong influence on who you are as a person today?
How would you describe your current mindset or outlook on life compared to the past?
What personal beliefs do you hold that you would never compromise on?
What motivates you in life?
How important are relationships to your overall well-being and happiness?
Can people make independent decisions, or do external factors heavily influence them?
Should the use of social media be limited?
What are the most important values to live a fulfilling life?
How do you stay mindful amidst noise and distractions?
When should you take a risk?
How do emotions affect our judgment of other people’s actions?
Do you think it’s possible to truly know someone without knowing their history?
What life lessons have you learned from failures?
Do you believe in second chances?
Can you recall a time when taking a risk paid off for you?
What do you think is the real power behind building meaningful connections with others?
Do you believe it’s possible to start from scratch and begin a new life for yourself?
How do you define true happiness for yourself?
How do you see the world differently than most?
What’s one core value that guides your choices and decisions in life?
Has anyone ever challenged their preconceived notions about you?
Are there moments of disbelief that have left a lasting impact on your understanding of reality?
What’s the key to finding true success in life?
What do you believe should never be compromised, no matter the situation?
Do you believe that our lives are determined by fate, destiny, or free will?
What makes someone truly beautiful to you?
Do you believe in miracles or the power of prayer?
What types of activities give your life purpose and significance?
Do you believe that people are capable of changing for the better?
What lifestyle choices lead to lasting happiness?
What’s the best decision you have made in life so far?
Do you feel that time can heal all wounds?
What basic message or lesson did you learn from your parents as a child?
Do you have a purpose greater than yourself that guides your daily actions?
What would you change about yourself if given the chance?
If you could tell your younger self anything, what would it be?
How do you decide which path to take when faced with difficult choices?
Do appearances sometimes deceive us when judging a person’s character?
What are things that bring out the best version of yourself?
Should we seize chances when they are there, or do they come around more than once in life?
What is one thing that everyone should experience at least once in their life?
If you had one wish to change the world, what would it be?
What does trust mean to you, and how is it earned?
If you could give your younger self one piece of advice, what would it be?

Truth or Dare Questions to Ask a Guy Over Text

Diving into a game of truth or dare can crank up the novelty of your text exchanges. With these daredevil prompts, you get to challenge him to be bold and reveal secrets, all while sharing laughs and playful banter.

Have you ever taken something that did not belong to you?
Who was your first crush?
What’s the craziest thing you have ever done?
What secrets have you never told anyone?
What do you think of when no one is around?
When was the last time you lied, and why?
If money were no object, what would be your dream job?
What is the most embarrassing thing that has ever happened to you in public?
Are there any dark secrets from your past that still haunt you today?
Would you rather tell someone a harsh truth or lie to them for their own good?
If you could take one item from this room and keep it to yourself, what would it be and why?
Have you ever cheated on someone, either emotionally or physically?
Are there any embarrassing moments that you still cringe at when you think about them today?
What is the craziest thing you would do for a friend?
Who was your first kiss, and where did it happen?
Have you ever cheated on a test?
Have you ever had a crush on a friend’s partner?
Have you ever been in love with someone who didn’t love you back?
Have you ever been involved in a physical fight?
When was the last time you lied, and why?
Have you ever had to apologize for saying or doing something mean to someone?
What do your friends think about you that is not true at all?
What’s the craziest thing you have done on a dare?
What is one thing you would not do under any circumstances?
What was the craziest plan you made but never carried out?
Have you ever told a white lie to get out of trouble?
Have you ever stolen something from someone?
Is there something embarrassing you want to confess to the group?
Have you ever broken someone’s trust?
Have you ever felt betrayed by someone close to you?
What do you regret not doing during your school years?
Have you ever been on a blind date?
Who would you want to be stranded on an island with?
If you had the chance, would you want to live forever?
What do your friends think is your best quality?
If you had the chance, would you parachute out of a plane?
If you only had one day to live, how would you spend it?
Would you rather be famous for one day and then be forgotten or remain unknown forever?
What is the worst decision you’ve ever made, and what did you learn from it?
What is the most embarrassing thing that has ever happened to you in public?
If you could do one thing differently in life, what would it be and why?
What is the craziest thing you have done in search of an adventure?
What would you do if you won the lottery?
Do you have any weird habits?
What is your guilty pleasure?
What is the strangest dream you have ever had?
Have you ever broken rules for fun?
What is the craziest thing you have ever done for love?
What is one thing you can do better than anyone else?
What has been your greatest epiphany in life so far?

Interesting Questions to Ask a Guy Over Text

When it’s time to strike up a good convo, interesting questions are like gold. They show you’re curious about the world and keen to hear his take on things. From the quirky to the profound, these questions can lead to conversations you’ve never imagined.

If you could have a conversation with any historical figure, who would it be and why?
What’s an odd talent you wish you had?
If you discovered a new planet, what would you name it?
What’s the most interesting documentary you’ve ever watched?
What’s a mystery or phenomenon you’d love to solve?
If you had your own talk show, who would your first guest be?
What’s the most fascinating era of history to you?
Have you ever had a truly unexplainable experience?
If you could learn one random skill instantly, what would you pick?
Which extinct animal would you bring back if you could?
What subject can you read about for hours and never get bored?
What’s a historical event you wish you could have witnessed?
What’s the strangest coincidence you’ve experienced?
If you could swap lives with one person for a day, who would it be?
What’s the most thought-provoking article or book you’ve read recently?
What does your dream home look like, and where is it?
What’s an invention that doesn’t exist but certainly should?
What’s a skill or craft you admire and wish you could master?
If you could have dinner with any fictional character, who would it be?
What’s something that’s normal now but might be considered weird in 100 years?
If you could have any mythical creature as a pet, which one would you choose?
What’s one conspiracy theory you find particularly intriguing?
If you could eliminate one thing from your daily routine, what would it be?
What’s something that everyone should try at least once in their lifetime?
If you could be guaranteed one thing in life (besides money), what would it be?
What’s a language you’d love to speak fluently?
What’s the most beautiful place you’ve ever been to?
Which science fiction gadget would you most like to own?
What’s an important life question that you don’t have the answer to?
What is something that recently made you rethink how you see the world?
If you could witness any event of the past, present, or future, what would it be?
What’s a piece of technology that you think has changed the world?
What’s the most unusual but fun activity you’ve taken part in?
What’s a personal challenge you’ve set for yourself recently?
What’s one thing you believe that many people don’t?
How would you describe your sense of humor with a movie title?
What is the most random thing you’ve ever watched all the way through on Netflix?
If you could explore any fictional world, which one would you choose?
What’s one thing you’ve never done but seemed fun to try?
If you could be any age for a week, what age would you choose and why?
What’s a piece of art that has deeply affected you?
What’s a societal norm that you think will be outdated in ten years?
Have you taken any personality tests? What did you think of the results?
What’s the weirdest thing you find attractive in a person?
If you could witness any fictional event from a book or movie, which would it be?
What’s a habit or trend from the past you’d like to see make a comeback?
If you could teleport to any place on Earth right now, where would you go and why?
What’s the most imaginative thing you did as a child?
What’s the most interesting thing you’ve seen or heard this week?
What’s your favorite myth, legend, or folklore story?

Questions to Ask a Guy Over Text to Start a Conversation

Kick-starting a chat can sometimes be the toughest part, but it doesn’t have to be. Armed with these questions, you’ll have no trouble breaking the ice. They’re your keys to unlocking days, or nights, full of engaging and easy-going banter.

Do you have any goals you are working toward right now?
What is the best advice you have ever received?
Who was your role model growing up?
What is the craziest thing you have ever done?
How did you spend your last vacation?
What is the most interesting place you have ever visited?
How do you usually spend your free time on the weekends?
Have you read a good book lately?
Do you consider yourself an optimist, pessimist, or realist?
What is something you are passionate about that not many people know about?
What has been your biggest accomplishment so far?
Do you prefer the city or nature for a day trip outing?
What helps you relax after a long day?
What color best describes your personality and why?
What have you always wanted to do but haven’t yet?
What makes you stand out from the crowd?
What area in your life could you use more help with right now?
What was the last movie you watched, and what did you think about it?
If you could pick any place in the world to visit, where would it be?
Do you prefer dogs or cats, and why?
If a genie granted you three wishes, what would they be?
What special skills or talents set you apart from others?
Are there any new skills or hobbies you’d like to try?
Do you enjoy learning new things?
Do you have any exciting plans for the future?
What do you like to do in your free time?
What kind of music do you listen to when you’re in a good mood?
What excites you right now?
What would be your dream job?
Who are some of the people who have had a big impact on your life?
What are you most proud of and why?
If money were no object, what dream would you pursue first?
What has been the most important moment in your life so far?
Do you have any personal growth goals you are currently working on?
What values guide your life choices?
Are there any upcoming events you’re excited about?
Do you prefer to stay home or go out with friends?
Are there any life lessons that have shaped who you are today?
If someone gave you a blank check right now, what would you do with it?
Do you have any favorite books, podcasts, or shows?
What do you find inspiring in life?
What would your ideal weekend look like?
Who are some of your favorite people to follow online?
Do you prefer city life or nature?
What always brings a smile to your face?
Who is the most special person in your life?
Do you prefer salty or sweet snacks?
Which do you like more, summer or winter?
Are there any places you’d like to visit someday?
When was the last time you laughed out loud?

Questions to Ask a Guy Over Text to See If He Likes You

These questions are subtly crafted to help you read between the lines. They offer a discreet way to gauge his interest and maybe even encourage him to share how he’s feeling. Because sometimes, a text can speak a thousand words!

Who is an important person in your life, and why do they matter to you?
What made you smile today?
What do you find most interesting about me?
Do you find me attractive?
If we could do anything together, what would it be?
Are there any topics you especially like to talk about with me?
What do you think about me?
Is it okay to talk about how I’m feeling with you?
How would you describe how I make you feel?
Would it bother you if I asked to hang out more often than normal friends do?
Do you ever get the impression that we’re connecting on a deeper level than just as friends?
Can I text you anytime, or is there a certain period when it’s better to contact you?
What kind of conversations do we have that you enjoy the most?
Do you remember the first thing we talked about when we first met?
How have we grown closer since we first started talking?
Is there anything special about me that stands out to you?
When something isn’t going well, can I count on you for support?
Do you feel comfortable sharing stories about yourself with me?
Are there moments that stand out to you where I made an impression on you?
Do you believe I can make some of your dreams come true?
What activities could we do together to help us grow closer?
What would you say is the most exciting thing that has happened since we started talking?
How do you feel after our conversations?
What is something special we can do together to celebrate special occasions?
Is there a moment we shared that seemed almost too perfect to be true?
What advice have you received from me that shaped your life?
How can I make our conversations enjoyable for both of us?
Do you believe we have something unique between us?
What do you value most when you talk to me?
Do you sometimes feel that we could grow closer through our conversations?
What is something special that only we share?
Do you sometimes feel like it’s easier to express yourself with me?
Are there common interests or beliefs between us that we could explore?
Do you ever find yourself looking forward to our conversations?
What kind of conversations are most meaningful to you?
Has there ever been a conversation between us that stuck in your mind?
Do our conversations have light-hearted moments or deep insights?
What experiences can we share to feel more connected?
Have you felt seen and understood through our communication unexpectedly?
Were there difficult topics that ended up being grateful for discussing?
What makes our conversations meaningful to both of us?
How did we grow with each other through our conversations?
What shared moments made you laugh or smile?
Do you smile at my messages?
Can I text you whenever I want to get in touch?
When do you feel happiest while being around me?
Do you ever catch yourself daydreaming about our future together?
Do I make your heart beat faster?
What do I do that makes it easy to talk to me?
Do I have the ability to make you forget your worries when we are together?

Frequently Asked Questions

How soon after texting a guy should you expect a response?

Response time varies greatly among individuals. While some reply immediately, others might take hours or even days, depending on their schedule and texting habits. Patience is key—avoid jumping to conclusions about delay.

How do I know if I’m texting a guy too much?

If the conversation feels one-sided, with you always initiating or sending multiple texts without a response, it might be time to ease up. Respect his space and allow the conversation to breathe – if he’s interested, he’ll reach out.

How often should I text a guy?

The frequency of text messaging should be comfortable for both parties. It’s important not to overwhelm the other person with too many messages. It’s a good idea to wait for the guy to respond before sending another message and to respect his communication style and boundaries.

Final Thoughts

Embarking on a text conversation with a guy can be as thrilling as it is daunting. But with the right questions, what starts as a flicker of curiosity can kindle into a connection worth nurturing.

Texting isn’t just about sharing words; it’s about opening doors to new worlds, experiences, and emotions. Each message is a stepping stone to understanding, a chance to laugh together, to think, to feel, and to grow closer, all with the gentle tap of a screen.

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