271 Dirty Questions to ask your Crush

Last Updated on February 2, 2022 by Alexander Burgemeester

Crushes are fun and exciting, but they’re also pretty scary. The mere thought of your person gives you butterflies, let alone speaking to them face to face. You get terribly nervous when you’re around him/her. Whether it’s a bright red face, or you’re stumbling over your words, your crush has an insane effect on you.

Not only that, but what the hell do you say when you want to talk dirty to someone you’re attracted to? Basically, they make you feel vulnerable, but according to intimacy educator Shan Boodram, this is a good thing.

Even when two people don’t know each other yet, vulnerability can help build a connection just with one conversation. Boodram actually advises getting right to the deep and meaningful conversations and avoiding small talk.

Plus, getting answers to the questions you really want to know can help you decide whether you want to take things further with your crush. It’s not uncommon to be super attracted to someone and then find out you’ve got no chemistry in the bedroom.

So to avoid that, here are 271 interesting questions you can ask a guy or a girl and find out everything you need to know about them. 

50 Dirty Questions to Ask Your Crush (over text)

If you don’t feel comfortable asking your crush dirty questions and having dirty talk face to face, you can do it over text?

You can let your guard down and have plenty of fun knowing that your person can’t see you cringing under the covers when you hit the send button revealing your secret fantasies.

If you want the conversation to keep going, but can’t think of any interesting questions to ask, here are 50 dirty questions to ask your crush:

50 Dirty Questions to Ask Your Crush (over text)
  1. What fantasy do you have about your celebrity crush?
  2. What is your favorite sex position?
  3. What is your least favorite sex position?
  4. Do you enjoy playing rough in the bedroom?
  5. How many positions do you like during sex?
  6. Have you ever taken a dirty picture?
  7. Have you ever sent anyone a nude picture by text?
  8. Would you have sex on the first date?
  9. What is the dirtiest thing you’ve ever done in the bedroom?
  10. What is the weirdest thing a partner has asked you to do?

Reading Suggestion: 246 Flirty Questions To Ask your crush while texting

  1. What is the wildest thing you’ve ever done in the bedroom?
  2. What is your favorite body part on a man/woman?
  3. Would you let someone give you a full body massage on a first date?
  4. Are you a boobs or a butt guy?
  5. Are you a yoga pants or a dress guy?
  6. How many girls would you sleep with at the same time?
  7. Have you ever had a dirty dream?
  8. What would your dream girl be like in bed?
  9. Do you have naughty dreams about your crushes?
  10. Would you ever play dirty truth or dare?
  1. What is it about a person that gives you butterflies?
  2. Do you like holding hands in public?
  3. Do you like kissing in public?
  4. Where is your favorite place to go on a date?
  5. Do you enjoy spontaneous sex?
  6. What position have you not tried?
  7. Where would you like to have sex outside the home?
  8. How do you like being teased?
  9. What would your bedroom bucket list be?
  10. What’s your idea of a wild adventure?
  1. Would you have sex in a store fitting room?
  2. What would you like to do to me if I was with you now?
  3. What would you say to me over text that you wouldn’t say to me face to face?
  4. How would you feel if I came over to yours with a trench coat and nothing underneath?
  5. What would you want me to do to you if I came over there right now?
  6. Would you feel comfortable sending me a naked picture?
  7. Is Netflix and chill your thing?
  8. On a scale of 1 to 10, what’s the sexual chemistry level between us?
  9. Would you invite me in if I turned up to your house unannounced in a bikini?
  10. What would you do to me if you only had five minutes?
  1. How would you react if I put my hand down your pants?
  2. What type of underwear are you wearing right now?
  3. Describe how you’re feeling right now?
  4. What would you do to me if I gave you a bottle of baby oil?
  5. Are we going to have some fun later?
  6. Since we’re going to be alone, what do you have planned for us?
  7. Send me a link of a sexy outfit you’d like to see me in?
  8. Do you prefer kissing or cuddling?
  9. Would you like me to make the first move?
  10. What do you think I look like naked?

Dirty 21 Questions to Ask Your Crush

When you have a crush on someone, you spend hours thinking about them, and you want to know every last detail about their life.

You’re intrigued by this person, they fascinate you and you’ve got a strong sexual attraction to them. To satisfy your curiosity, why not just ask them what you want to know?

Here are 21 dirty questions to ask your crush:

Dirty 21 Questions to Ask Your Crush
  1. When was the last time you had sex and who with?
  2. Do you enjoy having sex in public places?
  3. Would you ever have sex with someone a lot older than you?
  4. What is your idea of foreplay?
  5. How many times a night do you like to have sex?
  6. What song do you like having sex to?
  7. Which parts of your body do you like being kissed the most?
  8. What part of your body do you like being touched most?
  9. Have you ever hit it and quit it?
  10. What’s the best sex scene you’ve ever seen in a movie?

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  1. Would you dump someone because they won’t perform certain sexual acts?
  2. When are you the horniest, in the morning or evening?
  3. What do you do best in bed?
  4. Who did you have the best sex with, and why was it so good?
  5. What’s the longest you’ve gone without having sex?
  6. Can you keep going all night?
  7. Have you ever slept with a friend and then regretted it?
  8. Do you like dirty talk?
  9. What type of foreplay do you enjoy?
  10. Do you prefer to have the lights on or off during sex?
  11. Would you use sex toys on your partner?

Truth or Dare Dirty Questions to Ask Your Crush

Do you want to know if your crush has got any skeletons in the closet?

A fun way to find out is to play truth or dare. The more dares they choose over telling the truth, there’s a high chance that your potential lover has got something to hide.

Here are 50 truth or dare questions to ask your crush:

Truth or Dare Dirty Questions to Ask Your Crush
  1. Who in your office would you have a threesome with?
  2. What is the freakiest thing you’d want your partner to do to you?
  3. Who out of your friends do you want to sleep with the most?
  4. Would you sleep with someone of the same sex?
  5. Do you use sex toys when you’re alone?
  6. When was the last time you had an orgasm?
  7. Do you wear sexy outfits for your partner?
  8. Have you ever cheated on the person you’re dating?
  9. Would you sleep with anyone at your college?
  10. How many sexual partners have you had?

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  1. Have you ever had sex while your parents were in the house?
  2. Do you hug the opposite sex on purpose to get a feel of their body?
  3. What’s your favorite sexual memory?
  4. Would you ever pay for sex?
  5. Have you ever fantasized about your teacher?
  6. How do you go about trying to seduce someone?
  7. Have you ever made a sex video?
  8. Is there anything that turns you on that you find embarrassing?
  9. Have you ever worn women’s underwear? 
  10. What is the freakiest thing you’ve ever watched?
  1. Have you ever fantasized about your friend’s mother?
  2. Have you ever lied about your age to sleep with someone?
  3. Have you ever spied on me on social media?
  4. When was the last time you looked at porn?
  5. Have you had a dirty thought since we got on the phone?
  6. Have you ever not liked one of my outfits but lied and said you did?
  7. Do you find any of my friends attractive?
  8. Have you ever kissed yourself in the mirror?
  9. Name your guilty pleasure?
  10. What’s the most perverted thing in your web history?
  1. Do you have a secret crush on anyone I know?
  2. When was the last time you had a wet dream?
  3. Do you find any of your mom’s friends attractive?
  4. On a scale of 1 to 10, rate your level of sexiness.
  5. Is there anything you’d change about me?
  6. Have you ever looked through my phone?
  7. Have you ever done anything illegal?
  8. If you could, would you marry more than one person?
  9. If someone offered you $100,000 to sleep with their wife while you were dating me, would you do it?
  10. Am I the best looking person you’ve ever dated?

Reading Suggestion: 245 Sexual Questions To Ask Your Boyfriend

  1. Have you ever pleasured yourself in someone else’s house?
  2. Have you ever pleasured yourself in public?
  3. Have you ever left the house with no underwear?
  4. What are you afraid of in the bedroom?
  5. Do you see yourself having a long term relationship with me?
  6. Do you have a nickname for me I don’t know about?
  7. On a scale of 1-10, how dishonest are you?
  8. Do you find yourself attractive?
  9. Are you insecure about any part of your body?
  10. What was your last diary entry about me?

Dirty Flirty Questions to Ask Your Crush

Are you looking to take flirting with your crush one step further? If you’re considering sleeping with him/her, why not find out more about their sexual preferences to ensure that your first time is everything you hoped it would be.

Here are 50 dirty, flirty questions to ask your crush: 

Dirty Flirty Questions to Ask Your Crush
  1. Would you rather spend the night hugging or having sex?
  2. Have you ever thought about someone else other than the person you were having sex with?
  3. Would you want the girl to make the first move?
  4. Have I ever showed up in your dreams?
  5. On a scale of 1 to 10 how important is sex in a relationship?
  6. What do you like a woman to wear in bed?
  7. Do you have a favorite place you like to have sex?
  8. Are you aggressive in bed or are you shy?
  9. Do you prefer your girlfriend to dress sexy all the time?
  10. What do you find the most attractive about a woman?

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  1. What’s more important to you, physical attraction or sex appeal?
  2. Have you ever finished too quickly and felt embarrassed afterwards?
  3. When did you lose your virginity?
  4. Do you think you lost your virginity to the right person?
  5. Have you ever fancied your friend’s girlfriend?
  6. Do you prefer to make love or to have sex?
  7. What sexual act do you want to try but you’re too scared?
  8. Are you a giver or a receiver?
  9. Would you ask a girl to send you a nude picture? 
  10. What turns you off the most?
  1. Do you like giving or receiving love bites?
  2. What color underwear do you like females wearing the most?
  3. Have you ever had a crush on someone that was a lot older than you?
  4. What is your idea of the perfect date?
  5. What’s your best kept secret?
  6. Are you a hopeless romantic?
  7. What’s the most romantic thing you’ve ever done?
  8. What’s your idea of surprising your partner?
  9. How do you try and impress your date?
  10. In three words what’s your ideal man?
  1. In three words what’s your ideal woman?
  2. How do you let a person know you’re attracted to them?
  3. Do you prefer to be chased or to do the chasing?
  4. What is your best quality?
  5. If you could change anything about yourself, what would it be?
  6. Would you rather someone think you’re intelligent or sexy?
  7. Do you think it’s more important for a woman to have beauty or brains?
  8. Do you think you could pick me up?
  9. How do you know when you feel comfortable around someone?
  10. Who do you find attractive that no one else would?
  1. Would you answer the phone if I called you at 3 am in the morning?
  2. What’s your idea of a romantic vacation?
  3. What do you like wearing to bed?
  4. Which of your five senses would you give up if you had to?
  5. If I could read your mind what would I see?
  6. What do you want to get better at in the bedroom?
  7. Do you have any feminine qualities?
  8. Do you have any masculine qualities?
  9. What flavor ice cream would you like to lick off my body?
  10. What is the sweetest thing you’ve ever done for the person you were dating? 

Would You Rather Dirty Questions to Ask Your Crush

Are you tired of awkward and forced conversations? Or maybe you find it difficult to talk dirty with your crush.

Never run out of things to talk about with this interesting list of would you rather dirty questions to ask your crush:

Would You Rather Dirty Questions to Ask Your Crush
  1. Would you rather suck someone’s toes or lick the soles of their feet?
  2. Would you rather kiss with tongues or no tongues?
  3. Would you rather have sex with your work crush, or get a promotion?
  4. Would you rather see your mother or your father naked?
  5. Would you rather have sex in the rain or have sex in the snow?
  6. Would you rather accidently send a picture of your genitals to your mother or your neighbor?
  7. Would you rather wait until marriage to have sex or do it now?
  8. Would you rather have a hot body and a small penis, or a large penis and a terrible body?
  9. Would you rather have dirty talk or send dirty text messages?
  10. Would you rather be monogamous or have multiple partners?
  1. Would you rather have whipped cream or chocolate licked off your body?
  2. Would you rather go to a strip club or have your girlfriend dance for you?
  3. Would you rather be blindfolded or handcuffed while having sex?
  4. Would you rather send your sex video to all your social media followers or your parents?
  5. Would you rather meet the love of your life now or have $1 million?
  6. Would you rather have a threesome or go behind my back?
  7. Would you rather make out in the woods in the dark, or in an alleyway during the day?
  8. Would you rather get teased with an ice cube or hot wax?
  9. Would you rather dress up as a nurse or dress up as a playboy bunny?
  10. Would you rather have sex in the shower, or have sex in the bath?
  11. Would you rather have your back scratched, or have your hair pulled? 
  1. Would you rather have 50 orgasms a day, or never orgasm again?
  2. Would you rather sleep with an ugly person that gives amazing sex, or an attractive person that gives bad sex?
  3. Would you rather get caught having sex in real time, or have a video of you having sex get out?
  4. Would you rather your parents have access to your porn search history, or your boss?
  5. Would you rather keep your phone and never have sex again, or keep having sex and never have a phone again?
  6. Would you rather your mom catch you having sex or go out naked in public?
  7. Would you rather send naked pictures to your boss or send naked pictures to your ex?
  8. Would you rather participate in a sex party or just watch?
  9. Would you rather a video was released of you touching yourself or having sex?
  10. Would you rather have sex with a blow up doll or a really ugly female?
  1. Would you rather have a sugar daddy or beg for money on the street?
  2. Would you rather have sex with a porn star or the celebrity you fancy the most?
  3. Would you rather sleep with an ugly old man or woman or your ex?
  4. Would you rather be with a partner whose had a lot of sex or very little sex?
  5. Would you rather have sex in a hot room, or a cold room? 
  6. Would you rather have sex in the bathroom or the kitchen?
  7. Would you rather your best friends parents caught you having sex or your parents?
  8. Would you rather go to a strip club or a swingers club?
  9. Would you rather be with someone intelligent and bad in bed, or stupid and a freak in the sheets?
  10. Would you rather remain a virgin or lose your virginity to someone you don’t find attractive?

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  1. Would you rather watch your partner have sex with a stranger or her ex partner?
  2. Would you rather your one night stand leave after the first round, or stay for another round?
  3. Would you rather watch your friend have sex, or your friend watch you have sex?
  4. Would you rather have more foreplay, or more sex?
  5. Would you rather sleep with your celebrity crush or your high school crush?
  6. Would you rather sleep with an ex you hate or sleep with your enemy?
  7. Would you rather have only missionary sex or have sex in different positions?
  8. Would you rather show affection with your partner in public, or not at all?
  9. Would you rather have a threesome with women you’re not really attracted to, or have sex with one person you’re attracted to?

Dirty Freaky Question Game For Snapchat 

Are you getting bored of texting your crush? Why not try a new way of flirting with Snapchat.

The app allows you to add filters, take sultry selfies, add different backgrounds and play games.

These dirty freaky question games are a low-pressure way to ramp up the flirting with your crush:

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Dirty Freaky Question Game For Snapchat 
  1. What sex scene from a movie would you like to recreate?
  2. How long is a quickie to you?
  3. What would we do until we were rescued from a desert island?
  4. Would you ever go skinny dipping?
  5. Which country would you like to have sex in the most?
  6. Do you prefer sensual, or kinky foreplay?
  7. When do you feel the sexiest?
  8. What type of role play are you into?
  9. Has anyone ever caught you having sex?
  10. What type of porn do you like to watch?
  1. Have you ever had sex with someone at work?
  2. Would you ever have an orgy?
  3. Have you, or would you use food during foreplay>?
  4. Would you ever make a sex tape?
  5. What’s the first thing that gets your attention when you see someone you’re attracted to?
  6. Are you into BDSM?
  7. Do you have any fetishes?
  8. Do you enjoy reading erotic fiction?
  9. Have you ever been attracted to someone you shouldn’t be? 
  10. Do you have a high sex drive?
  1. Do you prefer to have a partner with a high sex drive?
  2. Have you ever had car sex?
  3. Do you like to be in control or do you like being submissive?
  4. Do you prefer to have long term partners or one night stands?
  5. Would you ever pay a woman to sleep with your friend?
  6. What type of sex would you like to have all the time?
  7. Do you prefer quickies or long sex sessions?
  8. Do you prefer to be loud or quiet during sex?
  9. Would you ever go to a swingers club?
  10. How far does your freakiness go?
  1. Could you remove my underwear with no hands?
  2. Do you like kinky sex?
  3. Have you ever been bored during sex?
  4. How long can you last without having sex?
  5. Do you prefer to have sex in the morning or at night?
  6. What does good sex mean to you?
  7. What’s something non-sexual that gets you aroused?
  8. What type of sex games do you like to play?
  9. What do you think about when you pleasure yourself?
  10. What does a sex vacation mean to you?

Reading Suggestion: Why is she ignoring me if she likes me?

  1. What type of music gets you in the mood?
  2. Have you fulfilled all your sexual fantasies?
  3. Would you ever spend the night just pleasuring a woman?
  4. Would you ever spend the night just pleasuring a man?
  5. Are you into spanking?
  6. Would you consider tantric sex?
  7. Where in your house do you like having sex the most?
  8. Would you like your partner to turn you on in public?
  9. What do you think about vibrating underwear?
  10. Do you like watching your partner pleasure herself? 

Tips on How to Flirt With Your Crush Over the Phone

Tips on How to Flirt With Your Crush Over the Phone

If you’re not a naturally flirtatious person, flirting will take you out of your comfort zone, and you’ll feel very uncomfortable. The good news is that like most skills, you can learn how to flirt, here are some tips:

Sound the Part

Get your crush to fall head over heels in love with you by having the sexiest voice ever. Keep your voice soft and calm, speak slower than normal by pacing your voice.

This will ensure the receiver hears every word you say, and fully digests each one as they roll effortlessly off your tongue.

Additionally, to give the impression of confidence, adjust the tone of your voice, deepening and lowering it as you speak.

Compliment Your Crush

Giving your crush a genuine compliment using a soft tone will get them very excited. Say something like, “I love the way you dress, you always look so sophisticated.”

Or you could impress them by giving him/her a compliment they’re less likely to hear such as, “I love how you take charge of every room you walk into, people are literally in awe of your presence.”

You can’t go wrong with compliments like this, not only do people like being praised, but they give the impression that you think outside the box because you haven’t given the average compliment about looks. 

Tell Your Crush How They Make You Feel

Telling your crush how you feel isn’t about confessing your undying love for them, you don’t want to do that as you’ll probably scare them off.

But you can Say something along the lines of, “your voice is so charming, it makes me feel really giddy inside.” Or, “the thought of kissing your lips has me tingling inside.” 

Hint That You Want to Know More

When people are interested in you, they want to know more about your life. Your person will be flattered that you’re asking, and they’ll be more than happy to give you extra details about their life.

Ask specific questions that will get you the answers you’re looking for. You can ask your crush to tell you more about their hobbies, family, previous relationships, career, and interests.

Make sure they’re leading questions so you can throw in some flirty responses, for example: Has anyone ever dumped you or broken your heart?” When they tell you about it, respond with something like: “she/he sure missed out on a hottie.” 

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Talk About Something You Remember About Them

Bonds are created through shared memories, so to deepen what you already have with your crush, you can talk about things like when you first met, the first time you heard him/her speak, how happy you were when you exchanged numbers, or the delightful smell of their cologne or perfume when you were first introduced.

You could say something like: “I remember the first time I heard your voice, I literally stopped breathing for a few seconds.” Or, “I’ve never forgotten the smell of your perfume/aftershave the first time we met. You smelt so hot, I was totally blown away.” 

Talk About Your Body Parts

Take things up a notch and give your person something to think about by mentioning your body parts.

As a guy, you could say something like, “my abs are seriously taking form with all these extra hours I’m putting in at the gym.” As a female, you might want to say something like, “my plump lips give the perfect kisses, and they can’t wait to meet yours.” 

Use the Right Body Language

Even if you’re speaking to your crush over the phone, the body language you choose to use will improve your confidence.

In fact, studies have found that body language affects the tone of our voice. Avoid crossing your arm over your chest, as this will make your voice sound harsh. Instead, sit casually, stroke your hair, and wear a bashful smile. This type of body language will help you sound more flirtatious.  

Final Thought

Whether you plan on texting or speaking to your crush over the phone or face to face, you’ve got the perfect list of interesting questions to find out everything you need to know about your beloved.

When you do get past the stage of crushing, you’ll be more than prepared to have the time of your life once you hit the sheets with your new partner.  

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Alexander Burgemeester

Alexander Burgemeester has a Master in Neuropsychology. He studied at the University of Amsterdam and has a bachelor's in Clinical Psychology. Want to know more?

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