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

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When you like someone or are at the beginning of a new relationship, one of the most exciting ways to get to know your crush is via text messages. Rather than sending them a dull message that reads, “Hey, what’s up?,” kick start the conversation with something spicy to ensure the texting continues late into the night.

Your goal here is to get to know your crush or true love better. If you need a little help with a conversation starter, these questions to ask a guy over text will give you all the inspiration you need. You can always fine-tune or tweak them to make them your own.

Flirty Questions To Ask A Guy Over Text

  1. Guess what I am wearing right now?
  1. If you could come to my dream tonight, what would you do?
  1. What do you think is my favorite piece of clothing?
  1. What is your favorite part of my body?
  1. Where do you want to be right now?
  1. Do you prefer cuddling or making out?
  1. What if you were shy, and I flirted?
  1. How do you feel about me?
  1. What do you wear to bed daily?
  1. What do you find irresistible in me?
  1. What is your idea of the perfect date?
  1. What’s your dirtiest fantasy?
  1. If we were to end up on an uninhabited island, what are the three things you’d want to have with us?
  1. How would you make me fall for you?
  1. If a girl was your type, how would you want her to seduce you?
  1. What are the signals you give a girl when you like her?
  1. What kind of physical touch best says, “I love you” to you?
  1. What’s your favorite place to be over the weekend? Does it include me?
  1. Do you prefer a pool or a hot tub?
  1. What would you do if I kissed you?
  1. Do you want a picture of me looking cute or naughty?
  1. If I show some skin on our picnic date, would you love it or hate it?
  1. What’s your favorite type of kiss?
  1. What are your thoughts on lingerie?
  1. Do you like talking dirty on the phone?
  1. If you were to see me naked, which part of my body would your eyes wander to?
  1. Would you rather see me in lingerie or nothing at all?
  1. What’s your favorite thing to do to me?
  1. Would you rather hug me for five seconds or kiss me for one second?
  1. What do you think my lips taste like?
  1. What would you do if I answered the door without my clothes on?
  1. What would you do to me If I’m with you right now?
  1. Name some amazing stuff you want me to do for you.
  1. What’s one of the most flirty things you’ve ever done?

Fun Questions To Ask Your Boyfriend While Texting

  1. If you were a girl for a day, what would you do?
  1. What’s the weirdest thing on your bucket list?
  1. What’s one of your most embarrassing stories?
  1. What is something that most people get wrong about you?
  1. What are a few funny pick-up lines you know?
  1. What are your top guilty pleasures?
  1. If you had X-ray glasses, which part of my body would you want to examine first?
  1. What’s the craziest thing you’ve ever done for a girl?
  1. Who was the last person you tried to impress?
  1. If a genie were to grant you one wish, what would you wish for?
  1. Do you believe in love at first sight?
  1. Who’s your couple role model that you’d want us to be like?
  1. What do you like to wear when no one’s around?
  1. How do you make small talk with a stranger?
  1. What kind of clothing do you like best on a woman?
  1. If you could teach every girl on the planet a lesson about men, what would it be?
  1. If your crush/ partner had a booger hanging out of their nose, would you tell them? If yes, how?
  1. Do you think a guy and a girl can be friends without catching feelings?
  1. How do two friends fall in love? Have you ever fallen for a girl pal?
  1. If you could spend an entire day with your crush, what would you do?
  1. What couples’ activity would you like to try in your spare time?
  1. Do you like big romantic gestures or simple ones?
  1. Do you think about me when I’m away?
  1. Have you ever flirted with a stranger online?
  1. Did someone ever stand you up?
  1. Have you ever been caught staring at a woman?
  1. Does being sneaky give you a thrill?
  1. What do you do when you’re watching your favorite movie with your parents, and that scene comes on?
  1. What small things or gestures make you smile even when you’ve had the worst day?
  1. What kinds of compliments do you like to hear?
  1. Someone walks into a room, and you smile from ear to ear; who is the person?
  1. What is your favorite thing about us?
  1. What is the one thing a woman can do to impress you instantly?
  1. What do you think your best physical feature is?
  1. Do you think you’d enjoy a love-hate relationship?
  1. What do you daydream about when you’re bored?
  1. Would you rather be unhappy but with the love of your life or incredibly happy but alone forever?
  1. Have you ever been caught in your birthday suit?
  1. Have you ever ghosted a girl?
  1. Have you ever stalked anyone on social media?
  1. What physical feature do you get complimented on the most?
  1. What’s the weirdest thing you have ever done to get a crush’s attention?
  1. Would you rather spend your spare time with your friends or me?
  1. How far would you go to land the girl of your dreams?
  1. What’s the craziest thing you have ever done to get noticed by a girl?
  1. If you can hire someone to do one thing that you can’t do yourself, what would it be?
  1. How long do you take to get dressed before the perfect date?
  1. Have you ever received any love letters?

Intimate Questions To Ask A Guy Over Text

  1. What was the first thing that you noticed in me?
  1. Do you have any secret fantasies?
  1. What is the most sensitive part of your body?
  1. What is your biggest turn on?
  1. Have you ever bought lingerie for someone?
  1. What is your idea of a perfect girlfriend?
  1. Have you ever had a dream about me?
  1. Would you describe yourself as more dominant or submissive?
  1. What would be your ideal first date?
  1. What’s the one thing that turns you off?
  1. Have you ever walked away from someone you still loved?
  1. Have you ever been in love with two people at the same time?
  1. Who would you want to be tied to for 24 hours?
  1. What are the qualities in a woman that you can’t resist?
  1. Have you ever roleplayed with a girl?
  1. Have you ever had a one-night stand?
  1. When’s the last time you felt butterflies in your stomach? And what caused them?
  1. How would you describe your perfect kiss?
  1. Do you like it when the girl makes the first move?
  1. Do you prefer asking flirty personal questions via texts or face to face?
  1. What are a few double standards you’ve experienced in your past relationships?
  1. What is the best thing you think a woman can do in bed?
  1. What is something you would really like to do with a girl but are shy to admit?
  1. How do you feel about kissing in public?
  1. Have you ever had friends with benefits?
  1. Have you ever used food during intimacy?
  1. When do I look the most beautiful to you?
  1. Have you ever laid in bed all day and just relaxed with someone?
  1. How big of a deal are special occasions for you?
  1. What type of scent do you like on a woman?
  1. How do you think you best express love?
  1. Outside of the bedroom, what can I do to keep the feelings of intimacy going all day?
  1. How would you know if I was the right person for you?
  1. Do you like biting?
  1. Do you like being teased?
  1. Have you ever kissed more than one woman in one day?
  1. What’s your favorite memory of us?
  1. What do you think reveals a lot about a person you’re dating?
  1. What have you always imagined doing with a girlfriend? Something that you’ve never done?
  1. What is the one temptation you can never resist?
  1. Do you believe in second chances?
  1. What is friendship to you?
  1. Do you think love is the same as lust?
  1. Is love about looks or personality to you?
  1. Have you ever lied to your partner to avoid an intimate moment?
  1. Do you sleep with a stuffed animal or something else for comfort?
  1. If you could undo anything from the past, what would it be?
  1. What is something that is absolutely off-limits in the bedroom?
  1. What’s your biggest sexual fear?
  1. Did you ever sleep with an ex?
  1. If I looked under your bed/ nightstand, what would I find?

Deep Questions To Ask A Guy Over Text

  1. What is your biggest weakness?
  1. What is unforgivable in your eyes?
  1. What cause are you most passionate about?
  1. Have you ever cried because of me?
  1. What’s your biggest insecurity?
  1. Have you ever wanted to cheat?
  1. Who are you most jealous of?
  1. What do you fear in a romantic relationship?
  1. Are you scared of commitment?
  1. If you could rewrite your past, what’s the one thing you’d change?
  1. What’s the one thing that helps you decide you can trust someone?
  1. Do you want to have children someday?
  1. Do you think you could treat a girl right?
  1. What is your opinion on hickies?
  1. What’s the one thing you’d never say to a crush?
  1. Who in your life brings you the most joy?
  1. Is there anyone or anything that you’d sacrifice your life for?
  1. What’s the one secret you’re still hiding from your ex-girlfriends?
  1. What do you look for in a girl?
  1. Do you let your friends’ opinions get in the way of your relationships?
  1. Do you think guys should always make the first move?
  1. If you could choose between a girl with lots of money or lots of love, who would you go for?
  1. What do you value the most in a healthy relationship?
  1. Do you believe in long-distance relationships?
  1. What does a happy and healthy relationship look like to you?
  1. Have you ever tried online dating? What’s the worst thing you experienced?
  1. Do you see me in your future? How?
  1. What’s the best romantic relationship advice you’ve received?
  1. What is the best part about being in a relationship?
  1. Do you think it’s okay to keep secrets in a relationship?
  1. What’s the best approach to resolving conflict?
  1. What quality in a woman keeps you the most interested?
  1. Could you ever forgive someone who cheated on you?
  1. How would you react if I gained a lot of weight, lose weight drastically, or become more muscular over time?
  1. How would you react if I changed my appearance drastically overnight?
  1. What major goals do you have for us?
  1. What is your opinion on marriage and children?
  1. If a crystal ball could tell the truth about you, your life, your future, or anything else, what would you want to know?
  1. Are we positively affecting each other’s life?
  1. What is the worst lie you ever told an ex?
  1. What is something you took for granted in your last relationship?
  1. What are the mistakes you always make while talking with a girl?
  1. What’s your take on splitting the bill in a restaurant?
  1. Do you prefer being single or in a romantic relationship?
  1. Do you think marriage is necessary before children?
  1. How long do you think you should be in a romantic relationship before you get engaged and married?
  1. Have you ever lied to impress a girl on a date?
  1. Do you think an age gap matters in a relationship?
  1. What role does physical attraction play in whether or not you should pursue a romantic relationship?
  1. Have you ever been in a one-sided relationship?
  1. What is the one biggest doubt you have about me in this relationship?
  1. How far would you go with someone you just met and will never see again?
  1. Who has had the biggest impact on your life?

Truth Questions To Ask A Guy Over Text

  1. Do you have something you always wanted to say to me but couldn’t?
  1. What’s the most embarrassing thing that you did while you were drunk? Describe in detail.
  1. Who is the one person you regret kissing?
  1. What would you do if you were stuck in an elevator with your ex?
  1. Did you ever get dumped on a text message?
  1. Have you ever had an inappropriate crush?
  1. Have you ever experienced true love?
  1. What’s the most romantic thing you have done in a while?
  1. What’s the one thing a woman has done for you that you will never be able to forget?
  1. Do you feel jealous when other men check me out?
  1. Do you have a crush on someone right now?
  1. Are you a romantic person?
  1. Have you ever kissed someone you shouldn’t have?
  1. What are the three qualities you look for in a potential date?
  1. Have you ever gone through a heartbreak?
  1. Would you mind telling me about the one who got away?
  1. How would you react to someone hitting on me?
  1. Who is your go-to person when you’re feeling down?
  1. Have you ever waited for my text message?
  1. What’s the biggest secret you’ve kept from your best friend?
  1. What’s the funniest pick-up line a girl has used on you out?
  1. What do you describe me to your friends?
  1. How would you feel if your girlfriend had a guy best friend?
  1. What is the one thing a woman should never do?.
  1. Have you ever broken someone’s heart?
  1. How many single girls’ numbers do you have on your phone?
  1. How many exes’ numbers are still on your phone?
  1. What do you think of my friends?
  1. Have you ever dated someone your family hated?
  1. Have you ever ignored my text message? Why did you do it?
  1. What’s your take on same-sex marriage?
  1. Do you believe that love is the most important thing in the world?
  1. Do you have a preference when it comes to blondes, brunettes, or redheads?
  1. Have you ever had the hots for your friend’s girlfriend?
  1. Do you have any feminine traits?
  1. Would you ever be in a polygamous relationship?
  1. Have you ever forgotten a special person’s birthday?
  1. Would you date your high school crush today?
  1. Who’s the ex you’d get back within a heartbeat?
  1. What’s the one thing you would never do in front of someone you had a crush on?
  1. Would you choose a calm and stable relationship or a wild, hot one?

Dare Questions To Ask A Guy Over Text

  1. I dare you to do seven push-ups and call out my name with each one.
  1. I dare you to put on lipstick and leave it for five minutes.
  1. I dare you to send me the funniest picture of you that you have on your phone.
  1. I dare you to write a short love poem about your true love.
  1. I dare you to write your crush’s name on your forearm using a permanent marker.
  1. I dare you to do a sexy dance standing on one leg.
  1. I dare you to wear all your clothing inside-out for an hour.
  1. I dare you to take a video of yourself drinking water like a dog.
  1. I dare you to keep an ice cube down your pants.
  1. I dare you to paint your fingernails blindfolded.
  1. I dare you to dance with no music on a video chat for one minute.
  1. I dare you to talk in a fake accent for the next ten minutes.
  1. I dare you to act like your favorite action hero for five minutes.
  1. I dare you to say something very intimate to me.
  1. I dare you to take off your shirt using only your teeth.
  1. I dare you to sing karaoke to your favorite song and send me a video.
  1. I dare you to send me a picture of your favorite body part.
  1. I dare you to send me a romantic text message explaining our first date.
  1. I dare you to catwalk across the room and send me a video.
  1. I dare you to find the oldest picture of us together and make it your profile picture for half the day.
  1. I dare you to sing the chorus of a cheesy song loudly.
  1. I dare you to walk like a lady in high heels.
  1. I dare you to draw a face around your belly button and send the picture to me.
  1. I dare you to apply make-up without looking in the mirror.
  1. I dare you to visit the most obscure website that comes to your mind and send me a screenshot.

When you’re texting your crush or true love, the key is to keep the intensity low and ask fun, lighthearted questions.  Asking interesting questions is an excellent and non-intrusive way to learn more about a guy from their childhood days to the present.

When it’s your turn to ask, or if your conversation is going nowhere, take your pick from these 250+ questions to ask a guy over text. Every question will fetch you the answers you seek without scaring your man away.