500+ Fun And Intimate Questions To Ask A Guy Over Text

250 Fun And Intimate Questions To Ask A Guy Over Text

Image: iStock

Texting is an easier and exciting way to get to know each other. You may be searching for questions to ask a guy over text at the beginning of a new relationship or when you start liking someone. Sending regular boring messages may end the conversation abruptly if they lose interest.

So why not kick-start the conversation with some exciting questions and keep the flow smooth. Read on for some questions to ask a guy over text and know them better. You may also tweak these questions to suit your style.

In This Article

Flirty Questions To Ask A Guy Over Text

Here are some flirty questions to ask a boy. Remember it is important to know the other person enough before selecting and asking the questions.

Guess what I am wearing right now?

If you could come to my dream tonight, what would you do?

What do you think is my favorite piece of clothing?

What is your favorite part of my body?

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Where do you want to be right now?

Do you prefer cuddling or making out?

What if you were shy, and I flirted?

How do you feel about me?

What do you wear to bed daily?

What do you find irresistible in me?

What is your idea of the perfect date?

What’s your dirtiest fantasy?

If we were to end up on an uninhabited island, what are the three things you’d want to have with us?

How would you make me fall for you?

If a girl was your type, how would you want her to seduce you?

What are the signals you give a girl when you like her?

What kind of physical touch best says, “I love you” to you?

What’s your favorite place to be over the weekend? Does it include me?

Do you prefer a pool or a hot tub?

What would you do if I kissed you?

Do you want a picture of me looking cute or naughty?

If I show some skin on our picnic date, would you love it or hate it?

What’s your favorite type of kiss?

What are your thoughts on lingerie?

Do you like talking dirty on the phone?

If you were to see me naked, which part of my body would your eyes wander to?

Would you rather see me in lingerie or nothing at all?

What’s your favorite thing to do to me?

Would you rather hug me for five seconds or kiss me for one second?

What do you think my lips taste like?

What would you do if I answered the door without my clothes on?

What would you do to me If I’m with you right now?

Name some amazing stuff you want me to do for you.

What’s one of the most flirty things you’ve ever done?

Are you ticklish?

Do you think of me before going to sleep?

Do you like me just as a friend or more?

What is a song that makes you think of me?

What do you think of my style?

What do you find irresistible about me?

What is your favorite type of kiss?

Are you attracted to my personality?

What is the sexiest thing I have done?

If I could grant you one wish tonight, what would it be?

What is your secret fantasy?

If we had a day all to ourselves, how would you want to spend it?

If we could go on a date anywhere in the world, where and what would you choose?

Do you like being wild in the bedroom?

What do you like most about the way I kiss?

What turns you on the most?

What is something that you’ve always wanted to try in bed, but haven’t?

What’s your favorite thing to do on a rainy day?

What’s your favorite thing to do on a lazy Sunday?

My parents are out of town. Would you like to come over?

Do you have a favorite pick-up line?

What’s your love language?

Do you prefer making the first move?

When was the last time you felt butterflies in your stomach?

Do you have a type?

How long did your last relationship last?

How long was your longest relationship?

When are you going to ask me out?

What’s the best way to ask someone out?

What are you thinking about right now?

What emoji makes you think of me?

Describe me in three words.

Have you told your friends about me?

Guess the emoji that’s next to your name on my phone.

What color do you think looks best on me?

What is something that sets me apart from other people?

Do you prefer being the big spoon or the little spoon?

What is your nickname for me?

What are your plans for the weekend?

Do you like hugs?

What are you cooking for me on our next date?

Where would you take me on a surprise date?

What is your favorite song to slow dance to?

If you could choose any place in the world to kiss me, where would it be?

If I was in a room full of people, would you still be interested in me?

If you were the lead character in a romantic novel or movie, what would you do to sweep me off my feet?

Have you had a dream about me?

Is there a particular item of clothing that you find me sexy in?

What’s our favorite romance scene in a movie?

When did you last check out my profile?

Where is your favorite place to kiss?

Is there anywhere where you’d like to be kissed more often?

Do you like cuddling?

Would you get a tattoo of my name?

Do you like to flirt?

What is your favorite thing about the way I touch you?

What’s your favorite thing that I wear to bed?

What do you think turns me on?

Fun Questions To Ask Your Boyfriend While Texting

Looking for some engaging conversation starters to text your boyfriend? Check out these fun questions to ask!

If you were a girl for a day, what would you do?

What’s the weirdest thing on your bucket list?

What’s one of your most embarrassing stories?

What is something that most people get wrong about you?

What are a few funny pick-up lines you know?

What are your top guilty pleasures?

If you had X-ray glasses, which part of my body would you want to examine first?

What’s the craziest thing you’ve ever done for a girl?

Who was the last person you tried to impress?

Quick tip

Avoid double texting to not come across as desperate. Wait for him to respond. As someone once said, consider texting as a tennis match. Serve first, then wait for him to send the ball before resuming play.

If a genie were to grant you one wish, what would you wish for?

Do you believe in love at first sight?

Who’s your couple role model that you’d want us to be like?

What do you like to wear when no one’s around?

How do you make small talk with a stranger?

What kind of clothing do you like best on a woman?

If you could teach every girl on the planet a lesson about men, what would it be?

If your crush/ partner had a booger hanging out of their nose, would you tell them? If yes, how?

Do you think a guy and a girl can be friends without catching feelings?

How do two friends fall in love? Have you ever fallen for a girl pal?

If you could spend an entire day with your crush, what would you do?

What couples’ activity would you like to try in your spare time?

Do you like big romantic gestures or simple ones?

Do you think about me when I’m away?

Image: IStock

Have you ever flirted with a stranger online?

Did someone ever stand you up?

Have you ever been caught staring at a woman?

Does being sneaky give you a thrill?

What do you do when you’re watching your favorite movie with your parents, and that scene comes on?

What small things or gestures make you smile even when you’ve had the worst day?

What kinds of compliments do you like to hear?

Someone walks into a room, and you smile from ear to ear; who is the person?

What is your favorite thing about us?

What is the one thing a woman can do to impress you instantly?

What do you think your best physical feature is?

Do you think you’d enjoy a love-hate relationship?

What do you daydream about when you’re bored?

Would you rather be unhappy but with the love of your life or incredibly happy but alone forever?

Have you ever been caught in your birthday suit?

Have you ever ghosted a girl?

Have you ever stalked anyone on social media?

What physical feature do you get complimented on the most?

What’s the weirdest thing you have ever done to get a crush’s attention?

Would you rather spend your spare time with your friends or me?

How far would you go to land the girl of your dreams?

What’s the craziest thing you have ever done to get noticed by a girl?

If you can hire someone to do one thing that you can’t do yourself, what would it be?

How long do you take to get dressed before the perfect date?

Have you ever received any love letters?

If you had to survive a zombie apocalypse, what three items would you take with you?

What superpower would you choose if you could only use it for menial tasks?

What is the most absurd thing you have ever done when you didn’t think anyone was looking?

Who would you choose to live with for a day, and what amusing circumstance do you imagine you would find yourself in?

What is the funniest memory you have from childhood?

Who would you choose as your team of three fictitious characters if you had to survive the zombie apocalypse?

What comedy movie or TV show do you always turn to when you want to laugh out loud?

If you could invent a new holiday, what would it be and how would you want people to celebrate it?

Have you ever been embarrassed in front of others that you can now laugh about?

What weird food pairing do you secretly enjoy?

If you could make your pet talk for a day, what do you think they would say?

Which ridiculous fashion trend have you ever worn?

If you had to coin a new term, what would you call it and what would it mean?

Which dad joke or pun is your favorite?

If you could spend a day in the life of a stand-up comedian, what would the subject of your performance be?

Which of these conspiracies do you consider to be the most absurd?

What TV show or movie is your guilty pleasure?

What team name and humorous mascot would you come up with for a made-up sports team?

What was the funniest or most embarrassing nickname you ever got as a kid?

What was the strangest dream you’ve ever had?

Who would you talk to and how would you make them laugh if you could have a chat with any historical figure?

What is your favorite meme?

What is your favorite pickup line?

Which Jeopardy category do you think you could win?

Has a pick-up line ever been used on you? Has it been a success?

Do you arrive at the airport early or just before boarding?

Who would you choose if you could trade lives with any TV or movie character?

Which made-up town or city would you most like to reside in?

Do you always have a fan on while you sleep?

When you sleep, do you snore?

Which holiday custom do you think we should establish together?

Would you be able to break a record? Why would that be used?

Which famous figure would have you in awe if you encountered them in person?

Which strangest discussion have you ever overheard?

What is the strangest food you’ve ever consumed?

What word do you find difficult to pronounce properly?

Do you walk around the house in slippers?

Do you prefer corded or cordless headphones?

Have you ever watched someone else’s phone in plain sight?

What is your favorite vice?

Do you believe pineapple has a place on pizza?

Which breed of dog would you choose to be if you could?

Is cereal soup?

Is a hot dog a sandwich?

What according to you is the best WiFi name?

What is the most useless invention of all time?

Do you like pineapples on your pizza?

Have you ever peed your pants?

Would you ever visit a nude beach?

How would you spend a million dollars?

What’s your favorite breakfast?

What if you had to play golf with a baseball bat?

Intimate Questions To Ask A Guy Over Text

Make sure you both know each other enough and feel comfortable discussing these topics and answering these questions.

What was the first thing that you noticed in me?

Do you have any secret fantasies?

What is the most sensitive part of your body?

What is your biggest turn on?

Have you ever bought lingerie for someone?

What is your idea of a perfect girlfriend?

Point to consider

Don’t go overboard while asking intimate questions to a guy. Also, refrain from asking questions that could put him in an uncomfortable spot.

Have you ever had a dream about me?

Would you describe yourself as more dominant or submissive?

What would be your ideal first date?

What’s the one thing that turns you off?

Have you ever walked away from someone you still loved?

Have you ever been in love with two people at the same time?

Who would you want to be tied to for 24 hours?

What are the qualities in a woman that you can’t resist?

Image: IStock

Have you ever roleplayed with a girl?

Have you ever had a one-night stand?

When’s the last time you felt butterflies in your stomach? And what caused them?

How would you describe your perfect kiss?

Do you like it when the girl makes the first move?

Do you prefer asking flirty personal questions via texts or face to face?

What are a few double standards you’ve experienced in your past relationships?

What is the best thing you think a woman can do in bed?

What is something you would really like to do with a girl but are shy to admit?

How do you feel about kissing in public?

Have you ever had friends with benefits?

Have you ever used food during intimacy?

When do I look the most beautiful to you?

Have you ever laid in bed all day and just relaxed with someone?

How big of a deal are special occasions for you?

What type of scent do you like on a woman?

How do you think you best express love?

Outside of the bedroom, what can I do to keep the feelings of intimacy going all day?

How would you know if I was the right person for you?

Do you like biting?

Do you like being teased?

Have you ever kissed more than one woman in one day?

What’s your favorite memory of us?

What do you think reveals a lot about a person you’re dating?

What have you always imagined doing with a girlfriend? Something that you’ve never done?

What is the one temptation you can never resist?

Do you believe in second chances?

What is friendship to you?

Do you think love is the same as lust?

Is love about looks or personality to you?

Have you ever lied to your partner to avoid an intimate moment?

Do you sleep with a stuffed animal or something else for comfort?

If you could undo anything from the past, what would it be?

What is something that is absolutely off-limits in the bedroom?

What’s your biggest fear about physical intimacy?

Did you ever sleep with an ex?

If I looked under your bed/ nightstand, what would I find?

What has been your most memorable or thrilling dating experience?

Do you have a favorite spot in mind where we could spend some private time together?

Would you mind sharing any of your hidden fetishes or turn-ons?

Which type of physical contact or intimacy makes you feel most gratified and desired?

Do you have any role-playing situations that you’ve always wanted to try?

What area of your body do you consider to be the most attractive, and why?

What would the perfect romantic evening with your partner entail?

Are there some words or phrases that turn you on?

How important is cuddling for you?

What do you think about experimenting in the bedroom?

Are you more of a planned or spontaneous person when it comes to intimacy?

Would you like to explore any specific fantasies or scenarios in the future?

How significant is physical intimacy to you in relation to emotional connection?

What is the most daring thing you have done in bed?

Do you like PDA?

Do you enjoy time spent with me in the bedroom?

Would you ever consider giving me lingerie as a gift?

How frequently should couples go on a vacation?

How frequently should married couples go on a date?

If you could date a celebrity, who would be it?

What are three things about me that you like the most?

What is one thing that you are afraid to tell anyone else?

What is your biggest regret?

If you could relive one day of our relationship, what would it be?

What do you think is missing from your life?

How would you like to change in the next year?

Which relative are you the closest to and why?

What would you change about the day we met?

Have you had any erotic dreams recently?

How many times a week should a couple meet?

How do you feel about being dominated in the bedroom?

Do you remember your first kiss?

What is the best romantic experience we’ve had?

Deep Questions To Ask A Guy Over Text

Here is a collection of deep and engaging queries to initiate meaningful conversations with a guy over text.

What is your biggest weakness?

What is unforgivable in your eyes?

What cause are you most passionate about?

Have you ever cried because of me?

What’s your biggest insecurity?

Have you ever wanted to cheat?

Who are you most jealous of?

What do you fear in a romantic relationship?

Are you scared of commitment?

If you could rewrite your past, what’s the one thing you’d change?

What’s the one thing that helps you decide you can trust someone?

Do you want to have children someday?

Do you think you could treat a girl right?

What is your opinion on hickies?

What’s the one thing you’d never say to a crush?

Who in your life brings you the most joy?

Is there anyone or anything that you’d sacrifice your life for?

Is there anyone or anything that you’d sacrifice your life for

Image: IStock

What’s the one secret you’re still hiding from your ex-girlfriends?

What do you look for in a girl?

Do you let your friends’ opinions get in the way of your relationships?

Do you think guys should always make the first move?

If you could choose between a girl with lots of money or lots of love, who would you go for?

What do you value the most in a healthy relationship?

Do you believe in long-distance relationships?

What does a happy and healthy relationship look like to you?

Have you ever tried online dating? What’s the worst thing you experienced?

Do you see me in your future? How?

What’s the best romantic relationship advice you’ve received?

What is the best part about being in a relationship?

Do you think it’s okay to keep secrets in a relationship?

What’s the best approach to resolving conflict?

What quality in a woman keeps you the most interested?

Could you ever forgive someone who cheated on you?

How would you react if I gained a lot of weight, lose weight drastically, or become more muscular over time?

How would you react if I changed my appearance drastically overnight?

What major goals do you have for us?

What is your opinion on marriage and children?

If a crystal ball could tell the truth about you, your life, your future, or anything else, what would you want to know?

Are we positively affecting each other’s life?

What is the worst lie you ever told an ex?

What is something you took for granted in your last relationship?

What are the mistakes you always make while talking with a girl?

What’s your take on splitting the bill in a restaurant?

Do you prefer being single or in a romantic relationship?

Do you think marriage is necessary before children?

How long do you think you should be in a romantic relationship before you get engaged and married?

Have you ever lied to impress a girl on a date?

Do you think an age gap matters in a relationship?

What role does physical attraction play in whether or not you should pursue a romantic relationship?

Have you ever been in a one-sided relationship?

What is the one biggest doubt you have about me in this relationship?

How far would you go with someone you just met and will never see again?

Who has had the biggest impact on your life?

What is your most attractive feature?

What scares you the most?

What was the best experience you had with a partner?

What are the traits you look for most in a partner?

What would the ideal day be like for you with a partner?

What are your life’s greatest goals and desires, and what steps are you now taking to pursue them?

Do you think that so far in your life, you have found happiness? If not, how would you define happiness?

What have you learned from your past relationships?

Do you have any cherished past experiences that have influenced who you are today?

What are your core beliefs and values, and how do they influence your relationships?

What are your long-term goals for us and how do you envision our partnership progressing?

How can you determine whether someone is genuinely the one for you?

How important are self-care and self-love in your life? How do you actually use it?

What, in your opinion, has been your most important life lesson to date?

Are there any pursuits you’ve always wanted to make but haven’t had the chance to do?

What does love mean to you?

What are your thoughts on fate or destiny in love? Do you think it’s true?

If you could go back in time, what advice would you give yourself?

What do you think the meaning and goal of life are?

How do you see making a difference in the world or in other people’s lives?

What view do you hold towards relationships and forgiveness?

Have you ever had a painful break up?

How do you maintain a healthy balance between your personal life, career, and relationships?

Which of your past decisions was the worst with regard to relationships?

What effect have your parents had on the way you feel about relationships and love?

What is non-negotiable in a relationship?

Do you ever feel that lying is acceptable? Under what circumstances?

What about yourself did you not know until someone else told you?

Do you fear growing old?

Would you ever compromise your dreams or goals in pursuit of love?

Do you think we are made for each other?

What is the most important lesson you will pass on to your children?

How have the things or qualities you valued changed over the years?

Do you like the way you look? Is there something you are insecure about?

How am I similar to your parents?

What have you learned about relationships from your parents?

What is the best part of our relationship?

What was your happiest moment with me?

If you had someone else’s life, who would it be?

How have you evolved as a person in the last five years?

Would you like to be famous?

What would your younger self think about our relationship?

Who was the last person you cried in front of?

Where do you see us in five years?

Is our relationship physical enough for your liking?

What do you want your final words to be?

Truth Questions To Ask A Guy Over Text

If you’re looking for some intriguing queries to text a guy and discover more about him, check out these truth questions!

Do you have something you always wanted to say to me but couldn’t?

What’s the most embarrassing thing that you did while you were drunk?

Who is the one person you regret making out with?

What would you do if you were stuck in an elevator with your ex?

Did you ever get dumped on a text message?

Have you ever had an inappropriate crush?

Have you ever experienced true love?

What’s the most romantic thing you have done in a while?

What’s the one thing a woman has done for you that you will never be able to forget?

Do you feel jealous when other men check me out?

Do you have a crush on someone right now?

Are you a romantic person?

Have you ever kissed someone you shouldn’t have?

What are the three qualities you look for in a potential date?

Have you ever gone through a heartbreak?

Would you mind telling me about the one who got away?

How would you react to someone hitting on me?

Who is your go-to person when you’re feeling down?

Have you ever waited for my text message?

What’s the biggest secret you’ve kept from your best friend?

What’s the funniest pick-up line a girl has used on you out?

What do you describe me to your friends?

How would you feel if your girlfriend had a guy best friend?

What is the one thing a woman should never do?.

Have you ever broken someone’s heart?

How many single girls’ numbers do you have on your phone?

How many exes’ numbers are still on your phone?

What do you think of my friends?

Have you ever dated someone your family hated?

Have you ever ignored my text message? Why did you do it?

What’s your take on same-gender marriage?

Do you believe that love is the most important thing in the world?

Do you have a preference when it comes to blondes, brunettes, or redheads?

Have you ever had the hots for your friend’s girlfriend?

Do you have any feminine traits?

Would you ever be in a polygamous relationship?

Have you ever forgotten a special person’s birthday?

Would you date your high school crush today?

Who’s the ex you’d get back within a heartbeat?

What’s the one thing you would never do in front of someone you had a crush on?

Would you choose a calm and stable relationship or a wild, hot one?

Can you spend a whole night awake?

Can you give up Netflix for a week?

What is your biggest regret in life?

Would you rather be poor and famous or rich and unpopular?

What was the most embarrassing experience you had?

What do you fear the most?

If you could switch lives with someone for a day, who would it be?

What is the most adventurous thing you have ever done?

What’s your secret talent or skill?

What is the craziest dare you have ever accepted?

What’s a childhood memory that makes you smile?

What is your favorite thing about being a guy?

What is something you like about your family and friends?

What is your favorite thing to do to make someone laugh?

What is your biggest accomplishment?

When was the last time you cried?

Who was the last person you searched for on Instagram?

Have you cheated in an exam?

What is your worst habit?

Why did your last relationship end?

What is the biggest mistake you have ever made?

Have you ever re-gifted a present you received?

Do you have a favorite sibling?

Have you ever practiced kissing in a mirror?

Have you ever kissed your partner on the beach?

Do you pee in the shower?

Have you peed in the pool?

What was your biggest childhood fear?

Do you have any superpower?

What is the best intimate experience you’ve ever had?

Have you been caught doing something you shouldn’t have done?

What’s the best date you’ve been on?

If you could get back with your ex, which one would you choose?

Dare Questions To Ask A Guy Over Text

If you’re looking for daring questions to ask a guy over text, here are some engaging queries to keep the conversation going.

I dare you to do seven push-ups and call out my name with each one.

I dare you to put on lipstick and leave it for five minutes.

I dare you to send me the funniest picture of you that you have on your phone.

Image: IStock

I dare you to write a short love poem about your true love.

I dare you to write your crush’s name on your forearm using a permanent marker.

I dare you to do an exotic dance standing on one leg.

I dare you to wear all your clothing inside-out for an hour.

I dare you to take a video of yourself drinking water like a dog.

I dare you to keep an ice cube down your pants.

I dare you to paint your fingernails blindfolded.

I dare you to dance with no music on a video chat for one minute.

I dare you to talk in a fake accent for the next ten minutes.

I dare you to act like your favorite action hero for five minutes.

I dare you to say something very intimate to me.

I dare you to take off your shirt using only your teeth.

I dare you to sing karaoke to your favorite song and send me a video.

I dare you to send me a picture of your favorite body part.

I dare you to send me a romantic text message explaining our first date.

I dare you to catwalk across the room and send me a video.

I dare you to find the oldest picture of us together and make it your profile picture for half the day.

I dare you to sing the chorus of a cheesy song loudly.

I dare you to walk like a lady in high heels.

I dare you to draw a face around your belly button and send the picture to me.

I dare you to apply make-up without looking in the mirror.

I dare you to visit the most obscure website that comes to your mind and send me a screenshot.

I dare you to do an impression of your favorite celebrity.

I dare you to pick someone from your contacts and sing them “Happy birthday.”

I dare you to blindfold yourself and pick something from your refrigerator and eat it.

I dare you to text your crush or ex something silly.

I dare you to create a funny TikTok and send it to your family group chat.

I dare you to wear your socks on your hands for an hour.

I dare you to take a shot of hot sauce.

I dare you to put on a Halloween costume and spend the day in it.

I dare you to send a voice note to someone you haven’t spoken to in ages, and tell them how much you miss them.

I dare you to make up a song about me.

I dare you to show me the messages you sent the last five people on your phone.

I dare you to let me choose who you DM tonight.

I dare you to keep three ice cubes in your mouth until they melt.

I dare you to eat a snack without using your hands.

I dare you to eat a piece of raw garlic.

I dare you to show me your orgasm face.

I dare you to eat a banana seductively.

I dare you to twerk for a minute.

I dare you to play air guitar for two minutes.

I dare you to pole dance on an imaginary pole.

I dare you to make yourself cry.

I dare you to try and put your fist in your mouth.

I dare you to try and lick your elbow.

I dare you to peel a banana with your toes.

I dare you to put on as many layers as you can in 60 seconds.

I dare you to remove two items of clothing.

I dare you to update your relationship status on Facebook to ‘engaged.’

Frequently Asked Questions

1. How do I know if I’m coming across as too aggressive or passive in texting conversations with a guy?

In written conversations, interpretation of the tone and intention depends entirely on the message’s receiver. However, you can be cautious by ensuring your language is clear and mindful. Avoid using slang or cuss words. Keep it fun yet respectful.

2. Is it okay to ask personal questions over text?

It depends on the kind of relationship you share with the person. To be on the safe side, be subtle in your approach. If they respond positively, you may ask the main question. If they seem reluctant, then drop the question right away. Do not pester them.

3. How do I transition from texting to a phone or in-person conversation with a guy?

To transition from texting to a phone or in-person conversation, you can suggest doing an activity together, like exploring a new restaurant or indulging in any activity. This can help you move beyond texting.

4. How do I make a guy comfortable opening up to me over text?

You need to make the guy feel comfortable by being respectful and supportive. Be responsive to his questions and encourage him to share more about himself without fearing being judged. Show interest in him, and he might be able to open up to you over texts.

Flirting with your boyfriend or crush on texts can be fun and thrilling. You can add a spark to your relationship, especially the couples in a long-distance relationship, by getting a little flirty and asking some intimate questions. Some questions to ask a guy over text can add excitement to your relationship and may help you know them better. So, why not initiate your conversation with some fun questions right away!

Infographic: How To Make Sure Your Flirty Texts Work

The above questions will spark chemistry and fuel the romance if you execute them well. You may have seen how sending the wrong texts can ruin a perfect relationship. So don’t make the same mistakes and follow the tips below to ace your flirting game and add emotions to the plain texts.

how to make sure your flirty texts work (infographic)

Check out this video for amazing questions to ask a guy over text messages! Get creative and have fun with it – you never know what kind of conversation you’ll have!