252 Exciting Flirty Questions to Ask Your Crush (While Texting)

252 Exciting Flirty Questions to Ask Your Crush (While Texting)

You and your crush have just recently become acquainted. Everything is thrilling, but there is a trace of trepidation in the air. Your dynamic can be taken to the next level by just asking the appropriate questions. 

252 Exciting Flirty Questions to Ask Your Crush (While Texting)

Flirt through text. Ask intimate, fun, daring and serious questions. Check out below the 252 examples of flirty and other types of questions to ask your crush while texting.

Intimate Questions to Ask Your Crush While Texting

You and this person are probably already incessantly exchanging messages. You’re certainly flirting with each other.

Texting is a simple method of communication, which is especially helpful in the beginning phases.

When you intentionally choose your conversation starters, you increase the connection between you and your partner and keep things enjoyable.

Woman using mobile phone while lying in bed

These are the most fun and flirtatious questions to ask the person you have a crush on! 

     1.  Can you guess what I’m wearing at the moment?

     2. What would you do if you could join me in my dream tonight?

     3. What do you consider to be my favorite outfit? 

  1. Which body part do you like best?
  1. What place would you like to be right now?
  1. Do you prefer making out or cuddling?
  1. What if I flirted when you were shy?
  1. What do you think of me?
  1. What do you wear every night to bed?
  1. What about me do you find captivating?
  1. What do you consider to be the ideal date?
  1. What is your most obscene fantasy?
  1. What three items would you want with us if we ended up on a deserted island?
  1. How could you entice me to love you?
  1. How would you like your ideal female to entice you?
  1. What signs does a guy offer a female to show her that he likes her?
  1. What sort of contact expresses my love for you the greatest physically?
  1. Where do you like to spend the weekends? Is that me included?
  1. Do you favor a hot tub or a pool?
  1. If I kissed you, what would you do?
  1. Would you like a photo of me appearing charming or sinister?
  1. Would you like or dislike it if I exposed some flesh during our picnic?
  1. What kind of kiss do you prefer?
  1. What do you think of lingerie?
  1. Do you enjoy having sexy phone conversations?
  1. Which area of my physique would draw your attention if I were naked?
  1. Would you rather see me naked or in lingerie?
  1. What do you like to do to me the most?
  1. Would you rather give me a five-second hug or a quick kiss?
  1. What flavor do you believe my lips have?
  1. What would you say if I opened the door whilst naked?
  1. If I were with you right now, what would you do to me?
  1. Please list some fantastic things I can do for you.
  1. What is the flirtiest thing you have ever done?
  1. What did you observe about me right away?
  1. Do you ever fantasize in private?
  1. Which bodily part is the most delicate?
  1. What makes you the happiest
  1. Have you ever purchased underwear for someone else?
  1. What qualities do you look for in a girlfriend?
  1. Have I ever been in your dreams?
  1. Which personality type best describes you—dominant or submissive?
  1. What kind of first date would you want?
  1. What is the one thing that you detest?
  1. Have you ever abandoned someone you were still in love with?
  1. Have you ever had simultaneous love for two people?
  1. To whom would you choose to be tethered for a day?
  1. What features of a lady do you find irresistible?
  1. Have you ever played a girl in a roleplay?
  1. Ever engaged in a one-night stand?
  1. When was the last time you had stomach aches? And what brought them on?
  1. How would you characterize the ideal kiss?
  1. Do you like it when the girl initiates contact?
  1. Do you prefer texting flirtatious personal questions or speaking to someone in


  1. Which of the following double standards have you come across in previous relationships?
  1. What, in your opinion, is the most pleasing thing a woman can do in bed?
  1. What do you want to do with a lady but are afraid to say?
  1. What do you think about public kissing?
  1. Have you ever had buddies with advantages?
  1. Have you ever fueled closeness with food?
  1. When do I appear to you as my most attractive self?
  1. Have you ever spent the entire day relaxing in bed with someone?
  1. How important are holidays and special events to you?
  1. What kind of fragrance do you enjoy on a woman?
  1. How do you believe you can show love the best?
  1. What can I do to maintain the sensation of closeness throughout the day except in the bedroom?
  1. How would you determine whether I am the appropriate match for you?
  1. Do you enjoy it being playfully bitten or nibbled on?
  1. Do you enjoy being made fun of?
  1. Have you ever kissed many women in one day?
  1. Which of our memories is your favorite?
  1. What do you believe says a lot about a date about them?
  1. What is it, something you’ve always seen yourself doing with a girlfriend? Anything you have never done before?
  1. Which temptation is it that are you are never able to resist?
  1. Do you think that second chances exist?
  1. What do you think a friendship is?
  1. Do you believe that passion and love are synonymous?
  1. In your opinion Is love more about personality or appearance?
  1. Ever tried to avoid an intimate moment with your partner by lying to them?
  1. Do you keep a teddy bear or stuffed toy comfort animal beside your bed?
  1. What would you change about the past if you could?
  1. What is the one thing you can never do in the bedroom?
  1. What sexual phobia scares you the most?
  1. Have you ever had sex with an ex?
  1. What would I find if I peeked beneath your bed or nightstand?

Fun Questions to Ask Your Crush While Texting 

Woman using mobile phone while lying in bed

  1. What would you do if you pretended to be a female for a day? 
  1. 87. What item on your bucket list is the strangest?
  1. What is one of your funniest stories?
  1. What is a misconception that most people have about you?
  1. What cute pick-up lines do you know?
  1. What are your favorite vices?
  1. What portion of my body would you want to look at if you had X-ray glasses?
  1. What is the most outrageous thing you have ever done for a woman?
  1. Who did you most recently try to impress?
  1. What would you ask for if a genie granted you one wish?
  2. Do you believe in love at first sight?
  1. What relationship would you like us to aspire to?
  1. When no one is around, what do you like to wear?
  1. How do you start a conversation with a stranger?
  1. Which type of attire do you like on a woman?
  1. What lesson about males would you want to impart to every female on earth?
  1. Would you inform your crush or potential partner if they had snot coming out of

           their nose – and how would you do it?

  1. Do you believe a man and a woman can be friends without developing romantic


  1. How does a friendship turn into love? Ever had feelings for a gal pal?
  1. What would you do if you could spend the whole day with your crush?
  1. Which date night activity for couples would you want to try?
  1. Do you like elaborate or modest romantic gestures?
  1. Do you think of me while I’m not around?
  1. Have you ever flirted online with a total stranger?
  1. Have you ever been duped by someone?
  1. Have you ever been discovered ogling a woman?
  1. Does being sly make you happy?
  1. What do you do when a sex scene appears in the movie you’re viewing with your parents?
  1. What insignificant acts or behaviors make you smile, even on your toughest days?
  1. What types of praises do you like receiving?
  1. Who would it be that when they enter a room, they make you smile from ear to ear?
  1. What do you like best about you and me?
  1. What is the one thing a lady may do to make you like her right away?
  1. What do you consider to be your finest physical trait?
  1. Do you believe a love-hate relationship would be enjoyable?
  1. When you’re bored, what do you fantasize about?
  1. Which would you choose—extremely happy but always alone, or sad but with the love of your life?
  1. Ever been caught wearing your birthday suit?
  1. Do you ever “ghost” women?
  1. Have you ever used social media to stalk someone?
  1. Which aspect of your appearance do others most often compliment?
  2. What is the strangest thing you have ever done to catch someone’s eye?
  1. Who would you choose to spend time with — your friends or me?
  1. How far would you go to get your ideal girl?
  1. What is the most outrageous thing you have ever done to catch a girl’s eye?
  1. What single action would you have someone else do for you if you could not do it


  1. How long does it take you to get ready for the ideal date?
  1. Do you have any examples of love letters?

Dare Questions to Ask Your Crush While Texting 

Man exchanging lovely messages with his girlfriend on phone at work

  1. I challenge you to perform seven pushups while yelling my name after each one.
  1. Put on lipstick and keep it on for five minutes if you dare.
  1. Send me the funniest selfie you have on your phone, I dare you.
  1. Write a few lines about your real love, I challenge you.
  1. I dare you to use a permanent marker to scribble your crush’s name on your


  1. Do a sensual dance while standing on one leg, I dare you.
  1. I defy you to spend an hour dressing entirely in reverse.
  1. I challenge you to record yourself guzzling water like a dog.
  1. I challenge you to keep an ice cube in your underwear.
  1. Paint your fingernails while wearing a blindfold, I dare you.
  1. I challenge you to spend a minute dancing silently during a video call.
  1. For the next 10 minutes, I dare you to speak with a false accent.
  1. For five minutes, I dare you to imitate your favorite action figure.
  1. Dare you to speak to me in such a private way.
  1. I challenge you to remove your shirt just with your teeth.
  1. I dare you to record yourself karaoke-ing to your preferred song and send it to


  1. Send me a photo of your favorite body part, I dare you.
  1. I challenge you to SMS me a love letter outlining our first date.
  1. I’ll email you a video if you will do a catwalk across the room.
  1. I challenge you to use the earliest photo of the two of us as your profile image for the first part of the day.
  1. I defy you to loudly sing the chorus of a corny love song.
  1. I challenge you to walk in high heels like a woman.
  1. I challenge you to make a face with your belly button and email me a photo of it.
  1. I dare you to apply makeup to your face without first checking in the mirror.
  1. You must go to the strangest website you can think of and submit me a screenshot.

Serious Questions to Ask Your Crush While Texting 

serious thinking african american guy wearing casual sending and getting messages

  1. What is your greatest flaw?
  1. What do you consider to be unforgivable?
  1. What issue do you care about most?
  1. Have you ever shed a tear over me?
  1. What is your biggest weakness?
  1. Have you ever been tempted to lie?
  1. Who makes you the most envious?
  1. What do you worry about in a love connection?
  1. Do you avoid committing?
  1. What is the one thing you would alter about your history if you could?
  1. What one factor helps you determine whether you can trust someone?
  1. Do you intend to have kids in the future?
  1. Do you believe you could properly treat a girl?
  1. How do you feel about hickies – both on the neck and other places?
  1. Which one phrase would you never utter to a crush?
  1. Who is the person in your life who makes you the happiest?
  1. Do you have a person or something you would give your life for?
  1. What one thing are you keeping a secret from your ex-girlfriends?
  1. What qualities do you want in a girl?
  1. Do you let the opinions of your friends interfere with your relationships?
  1. Do you believe that men should always initiate contact?
  1. Which would you choose—a girl with plenty of money or a girl with loads of love?
  1. What do you think makes a relationship healthy?
  1. Do you think long-distance relationships are possible?
  1. What does a contented, wholesome relationship seem to like to you?
  1. Have you tried dating online? What was the worst experience you ever had?
  1. Do you foresee a future with me and how?
  1. What relationship advice has been most helpful to you?
  1. What aspect of being in a relationship is the best?
  1. Do you believe that keeping secrets in a relationship is acceptable?
  1. What method of dispute resolution works the best?
  1. What about a lady most intrigues you and piques your interest?
  1. Would you ever be able to forgive a partner who cheated on you?
  1. How would you feel if I put on a lot of weight, or lost a lot of weight quickly, or started to acquire muscle over time?
  1. What would you think if I radically altered my look overnight?
  1. What are your main objectives for us?
  1. What are your views on getting married and having kids?
  1. What would you want to know if a crystal ball could reveal the truth about you, your life, your future, or anything else?
  1. Do we make a difference in one other’s lives?
  1. Which of your lies to an ex was the worst?
  1. In your previous relationships, what was it that you took for granted?
  1. What blunders do you consistently make when conversing with women?
  1. What are your thoughts on dividing a meal bill?
  1. Which would you rather have: a romantic give and take relationship, or being single, doing whatever you want and not sharing with anyone?
  1. Do you believe having children comes before being married?
  1. In your opinion, how long should a love relationship last before getting engaged and married?
  1. Have you ever lied to get a date with a girl?
  1. Do you believe that a relationship’s age gap is important?
  1. What part does physical appeal play when deciding whether or not to pursue a romantic relationship
  1. Do you have any experience with one-sided relationships?
  1. What is your greatest apprehension about me in our relationship?
  1. What lengths would you go to for someone you’ve just met and won’t see again?
  1. Who has affected your life the most?
  1. Do you have anything you’ve wanted to speak to me about but have been unable to?
  1. What is the most humiliating thing you have ever done while intoxicated?
  1. Which one of your kisses did you regret?
  1. What would you do if you and your ex were stranded in an elevator?
  1. Have you ever received a text message rejection?
  1. Ever had an unsuitable crush?
  1. Have you ever known real love?
  1. What recently did you do that was the most romantic?
  1. What is the one act of kindness a lady has provided for you that you will never forget?
  1. Do you become envious when other guys look at me?
  1. Do you currently have feelings for anyone?
  1. Are you romantically inclined?
  1. Ever given someone a kiss that you shouldn’t have?
  1. What are the top three characteristics you want in a possible partner?
  1. Have you ever experienced heartache?
  1. What happened to the one that got away?
  1. What would you do if someone touched me?
  1. Who do you turn to first when you’re feeling down?
  1. Have you ever kept an eye out for my text?
  1. Which of your greatest secrets have you concealed from your best friend?
  1. What is the most hilarious pick-up line a female has ever used on you?
  1. What do your friends say about me?
  1. What would you think if your girlfriend had a close friendship with a man?
  1. What is the one thing a lady should never do?
  1. Have you ever hurt someone else’s feelings?
  1. How many phone numbers of single girls do you have?
  1. How many ex-partners’ phone numbers still exist on yours?
  1. How do you feel about my friends?
  1. Have you ever dated someone who your family disliked?
  1. Have you ever dismissed a text I sent you, and if so, why?
  1. What are your thoughts on same-sex unions?
  1. Do you think that the greatest value in the world is love?
  1. Do blondes, brunettes, or redheads seem to appeal to you more?
  1. Have you ever harbored feelings for the girlfriend of a friend?
  1. Have you got any feminine qualities?
  1. Would you ever be involved in a polygamous union?
  1. Have you ever overlooked someone special’s birthday?
  1. Do you still want to date your high school sweetheart?
  1. Who is the ex you would instantly get back with?
  1. What is the one thing that you would never do in front of a crush?
  1. Which would you prefer: a cool, steady relationship or a hot, crazy one?

Why Is It Helpful to Ask Flirtatious Questions to Get to Know Your Crush?

The mating process involves several natural activities, one of which is flirtation. It has its origins in our biology and history, and it is a fundamental method by which we communicate our interests to one another.

You may learn more about another person by asking them flirtatious questions. It relieves the burden of having to talk seriously right then and there. At the same time, it has the potential to reinforce a feeling of closeness unintentionally.

It’s an excellent method to take the first step toward beginning a romantic relationship.

One of the most interesting things you may ask your crush is their opinion on various pieces of romantic, sexual, or material relating to relationships.

This accomplishes two different goals:

In the first place, it demonstrates that you have an interest in learning their viewpoint on personal matters.

Secondly, it provides you with helpful information about the person, which may assist you in determining whether or not you genuinely want to pursue a romantic connection with them.

The best flirting inquiries strike a healthy mix between sexuality and inquiry.

At first, the flirtatious behavior could be slightly understated, but as things advance, the intentions will often become more evident.

What is the Proper Way to Flirt Through Text?

It’s possible that flirting by text is simpler than flirting in person. You have more time to ponder and analyze your comments when communicating via text.

Before you blurt something out, you might want to check over what you’ve written first, or perhaps give it to a buddy to read and comment on.

It is preferable to keep communications to a minimum length. You don’t want to bore your crush to death by writing interminable lines about yourself.

Flirting should also involve being upbeat and lively; you want to demonstrate your best qualities.

In conclusion, you shouldn’t dismiss the usefulness of an emoji when it’s used in the right context. Whether it’s a wink, a smirk, or a kiss, those teeny-tiny expressions may greatly impact the way you come across!

Final Thoughts on 252 Exciting Flirty Questions to Ask Your Crush (While Texting) 

Texting the person, you have a crush on may be a fun and exciting way to flirt.

Suppose you and your partner are in a long-distance relationship. In that case, you may rekindle the flames of passion in your connection by engaging in some playful teasing and by posing some personal questions to one another.

Texting questions to a guy or a gal may be an exciting way to deepen your connection with them and gain a deeper understanding of who they are as people.

Why not go right into your chat with some questions that are both interesting and exciting to answer, and see what happens?

Patricia Godwin

Patricia has many years of experience as a content writer on various subjects, and she is the Editor of Lifestyle Divorce. Patricia’s worked as the Practice Manager at an International Divorce and Family law firm for over 15 years. She is a qualified Counsellor, and she has had many counselling sessions with people considering or going through a divorce.

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