244 Flirty & Dirty Questions to Ask Your Crush

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So, you have a crush on this guy, and you want to flirt with him a little, right?

Great!

Flirting with your love interest is good for your relationship. However, there may be times when you want to lighten the mood, have some fun, or turn this guy on. That is the best time to make use of your flirting skills.

You can ask flirty and dirty questions to get him in the mood. In fact, these questions can be great to know how your crush is in bed or how his sex life is. And this conversation may lead to something good – you never know!

In my dating days, my boyfriend and I used to talk for long hours over the phone as we were in a long-distance relationship. And on days when our timings didn’t match, we used to chat over texts.

We used to play this fun game of asking questions whenever we needed a fun element in our relationship; as you know, long-distance relationships can be very difficult at times. And it can be emotionally draining too.

So, from my experience, I can assure you that asking naughty questions to your crush or boyfriend works wonders. I can change the entire mood in an instant, and you are left wanting each other more.

Now, if you are wondering what questions would be appropriate to ask, I have listed here some dirty questions to ask your crush. Of course, you can modify them according to the stage of your relationship.

Without further ado, read on.

Dirty Questions to Ask Your Crush

Come, let’s raise the temperature of your conversation with your crush!

Naughty Questions to Ask Your Crush

Well, it’s never too late to be naughty, dear!

• Do you have any fantasies about your celebrity crush? What is it?

• What is the weirdest memory you have of a fling?

• What is the weirdest thing you’ve ever done with your partner?

• Has your partner ever asked you to do anything weird?

• Have you ever found anything weird, but you have done that just because your partner has asked you to do it?

• Have you ever forced anyone to sleep with you?

• Has anyone ever forced you to sleep with them?

• What, according to you, is the dirtiest thing that you have ever done in bed?

• Have you ever been involved in oral sex?

• What are your views on oral sex?

• Have you tried sex in a different way than normal?

• Have you ever been involved in a threesome?

• What are your views on the threesome?

• Do you like to experiment in bed?

• How many sex positions have you tried in bed to date?

• What is your favorite sex position?

• What is the most underrated sex position, according to you?

• What is the most overrated sex position, according to you?

• Do you like to try new sex positions in bed, or are you okay with the limited number of positions and don’t want to try anything new?

• Have you ever gotten hurt during sex while trying a new position?

• Have you ever ended up laughing while trying a new position?

• How open are you to same-gender sex?

• Have you ever slept with someone of the same gender as you? How was your experience?

• Have you ever clicked a nude picture of yourself and sent it to someone by mistake?

• What is the biggest blunder that you have ever made in bed?

• What is the most satisfying memory you have of having sex with someone?

• What is the worst memory you have of having sex with someone?

• Have you ever slept with someone to get an opportunity?

• Have you ever rejected having sex with someone because you didn’t like that person?

• Do you enjoy a calm sex session?

• Do you enjoy a rough sex session?

• How naughty are you in bed?

• What is the biggest compliment you ever got from your partner for your bedroom moves?

• Have you ever got any compliments from your partner for your amazing bedroom moves?

• How much would you rate yourself for your bedroom moves on a scale of one to ten?

• How many positions do you like to try in bed?

• Do you have any weird fantasies that you want to try with your partner?

• Have you ever got caught having sex in some place where it was not allowed?

• What are your views on car sex?

• Do you want to be intimate with your partner in unusual places, or are you fine with the usual places?

• Have you ever taken some really dirty picture of yourself, and then someone saw it on your phone?

• What is the weirdest place you have ever made out?

• What are your views on sex on your first date? Are you up for it?

• What is the wildest memory you have in bed?

• What, according to you, is the sexiest body part of a man and a woman?

• What is the one body part that you are attracted to the most?

• Do you have dirty dreams often?

• Have you ever woken up suddenly in the middle of having a dirty dream and then went to sleep again so that you could continue having that dream?

• Do you remember your favorite dirty dream?

• What, according to you, is being dirty in bed?

• If you ever get the chance to sleep with your favorite celebrity, who would it be?

• If you are on your first date with someone and they say that they want to give you a hot full body massage, how would you react?

• Would you like to play sexy truth or dare with your partner? What would you choose – truth or dare?

• What kind of a person are you – casually dressed or suited?

• How many crushes do you have at the moment?

• Do you have dirty dreams about your crushes?

• What would your dream partner be like in bed?

• What is that one sex move that you want to try with your partner the next time you are together?

• Have you ever got butterflies in your stomach seeing or talking to someone?

• How would you react if the person you like confesses their feelings for you first?

• What kind of places would you like to go on dates to?

• Do you like boobs or butts more?

• If you were to choose between a girl with good looks and a girl with good intelligence, which one would you choose?

• Do you like girls wearing specs?

• Do you like public displays of affection?

• Do you like to hug your partner in public?

• Would you like to make out in public?

• Have you ever said something to your partner during sex that you regretted later?

• Have you ever had drunk sex?

• How have you ever kissed someone while you were drunk?

• What are your views on spontaneous sex?

• What other places would you like to have sex other than your bed?

• Is there any sex position that you have not tried yet, but you really want to?

• Have you ever tried a new position that you saw in a magazine, and then it turned out to be totally different than you imagined it to be?

• If a girl wants to make you hard by teasing you, would you like it?

• How would you like to be teased?

• Is there anyone who can make you hard without even touching you?

• Do you find me sexy?

• What does your bedroom bucket list look like?

• Would you like to have a wild and sexy adventure with a stranger?

• Have you ever had sex with a stranger?

• Have you ever had a crush on a stranger?

• How many one-night stands have you had to date?

• Are you more of a serious relationship kind of a person, or are you more of a fling person?

• What is your favorite sex move?

• What does your bedroom bucket list look like?

• What if you get turned on in a shopping mall? Would you have sex in the dress trial room?

• If I were there beside you now, what naughty things would you do me?

• Suppose I am with you right now, and I give you five minutes. What would you do to me?

• If I knock on your door wearing a trench coat and nothing underneath, how would you feel?

• Would you tell me to enter your house if I went there wearing just a bikini?

• What is your favorite dress you like on me?

• If I ask you to rate my looks on a scale of one to ten, how much would you rate?

• How hot do you think I am?

• Am I sexy to you?

• Do you think we look good together?

• Do you think we have good chemistry between us?

• If I ask you to rate the chemistry between us, what would be your answer?

• If I ask you to take a snap of yourself without wearing anything and then send it to me, would you do it?

• Do you feel comfortable when you are with me?

Read More: 10 Thoughtful Questions to Ask Your Crush

Deep Dirty Questions to Ask Your Crush

Let’s dig deeper into the game of naughtiness!

• Do you think we click?

• Is there anything that you want to ask me but haven’t asked yet?

• Is there anything that you prefer to ask me via text without asking face to face?

• Would you like to have some fun with me?

• Have you ever found me in your dreams?

• Have you ever seen me naked in your dreams?

• Have you ever wanted to do naughty things to me in your dreams?

• Have you ever dreamt of something but wanted to do it badly in reality too?

• If we were in the back seat of a car going somewhere, and I put my hands inside your pants, what would be your reaction?

• Can you tell me the color of the underwear you are wearing now?

• What if I ask you to remove your underwear and send me a picture of how you look without it? Would you send it to me?

• How are you feeling right now? Can you describe it?

• Suppose I am with you right now. What would you want me to do to you?

• I want to see you naked right now. Can you send me a picture of your hot body?

• I want to touch your body right now. Do you want me to come over?

• How would you feel if I made the first move?

• What are your thoughts on phone sex? Are you up for it?

• I am feeling needy of your touch right now. Can you come over?

• What do you think my touch can do to your naked body?

• Would you like it if I moved my naked body up your naked body?

• How do you feel when I look at you all needy?

• Can you go on a date tomorrow where we can be a bit naughty with each other?

• What is your favorite place where you want to meet me?

• Is there any special place where you want to cuddle with me?

• I am on a buying spree now. Can you send me the picture of the lingerie you want to see me in the next time we meet?

• What are the things that you want to do for me?

• Do you want to try something new with me?

• What do you like more: cuddling or kissing?

• What if we are together and I give you some baby oil? What would you do with it?

• What is your plan for tonight? How about having some fun together?

• What do you think I look like without clothes?

• How frequently do you masturbate?

• How do you feel after you masturbate?

• Do you picture me in your head when you masturbate?

• Do you have a sex playlist?

• Would you like to have a sex playlist?

• Do you like to turn music on while having sex?

• What is your favorite music for having sex?

• Does music during sex make everything better? What are your views on this?

• Do you like foreplay?

• How often do you like to have sex?

• When was the last time you slept with someone? Who is that someone?

• Do you want to have sex in public places?

• Have you ever had sex in water?

• Have you ever had sex in a car?

• Have you ever had sex in an airplane?

• Is there any song that turns you on?

• What would you do if you got a chance to have sex with an older woman?

• What is your favorite body part that you want me to touch?

• What, according to you, is the best sex scene in a movie?

• Is there any movie sex scene that you liked so much that you want to recreate it in real life?

• Where do you want to be kissed the most?

• How much time do you last in bed?

• How many times can you cum in one night?

• What is the best one-night stand experience you have had?

• Did you ever get hard seeing someone you never imagined you would?

• What type of girl do you want to be a partner with?

• How wild are you in bed?

• What is the longest time you have lasted in bed?

• Do you like to perform oral sex on your partner, or do you like to receive oral sex from your partner? What do you prefer more?

• What is your favorite memory of a sexual encounter?

• Have you slept with someone just because you wanted something from them?

• Can you remember your last sex dream?

• What, according to you, is the best kind of foreplay?

• What are your views on sex toys?

• Do you want to use sex toys while having sex?

• Do you like to be loud during sex?

• If your partner is loud during sex, does it make you more excited, or do you get turned off?

Also Read: Signs He is Making Love to You

Exciting Dirty Questions to Ask Your Crush

It’s time to know your crush’s past sex life!

• Have you slept with your ex and then regretted it later?

• With whom did you have the best sex ever?

• What is the longest time that you have gone without sex?

• What is the one thing that can make you hard the moment you see it?

• What is your best move in bed?

• What kind of beast are you in bed?

• Do you like it slow, or do you like it rough?

• What is your preference during sex: lights off or lights on?

• When do you feel horny the most: morning or evening?

• When was the last time you watched an adult movie?

• Do you have any favorites in your adult movie collection?

• Who is your favorite adult movie star?

• Do you remember the first time you saw an adult film?

• How old were you when you saw an adult movie for the first time?

• How old were you when you masturbated for the first time?

• How old were you when you lost your virginity?

• How did you feel when you had sex for the first time?

• How old were you when you had your first kiss?

• Do you remember your first crush?

• Have you ever dreamed of having sex with someone you hate in real life?

• Have you ever accidentally seen someone having sex? What was your reaction?

• What is your deepest, darkest wild fantasy?

• Did you break up with someone because they were not good in bed?

• Is there anyone in your office that you would like to have a threesome with?

• Is there anything silly that you want your partner to do in bed?

• Is there any crazy act that you want your partner to perform in bed?

• Have you ever done anything in bed that spoiled the entire mood of your partner?

• Has your partner ever done anything that spoiled your mood of having sex?

• Do you like to dress up for me?

• How interested are you in me?

• Do you use your hands or sex toys while you are alone?

• Which one do you prefer more: your hands or sex toys?

• How did you feel when you had your first-ever orgasm?

• Are there any of your friends that you have secretly desired once?

• Would you wear a sexy dress for me?

• How many people have you had sex with?

• Have you ever used the window to get into your partner’s house and then spent the night there?

• Have you ever worn women’s lingerie?

• What is the freakiest sex position you have watched in adult movies?

• What is the one thing that you really want to try in bed, no matter how weird it may seem to your partner?

• Have you ever made your sex tape?

• If I ask you to seduce me, what would you do?

• Have you ever fantasized about having sex with your teacher?

• Have you ever paid for sex?

• What are your views on paying for sex?

• Have you ever hugged someone of the opposite gender just to get a feel of her body?

• Did it ever happen to you that you were having sex in your room when your parents were outside, and suddenly you heard them opening the main door?

• Have you ever fantasized about someone that you are really embarrassed to admit?

• Have you ever stalked me on social media?

• Have you ever wanted to kiss me in public?

• Have you ever wanted to sleep with someone so much that you lied to them about your age?

• Now that we are talking on the phone, have any dirty thoughts crossed your mind?

• Have you ever looked at your mirror and kissed yourself?

• When was the last time you opened an adult site?

• What is the worst kissing experience you have, and with whom?

• Do you find any of my friends sexy?

• Was there any time when I came to you wearing something that you didn’t like, but then you lied to me, saying that I was looking good?

• If I go to your web browsing history, what is the most perverted thing I will find?

• Have you found any of your mother’s friends attractive?

• How often do you have wet dreams? When was the last time you had it?

• Do you have any secret crush on your friend list?

• If I ask you to rate yourself in terms of your sexiness, how much would you rate on a scale of one to ten?

• How well do you think I am in bed?

• How many people have you dated till now?

• Do you regret having dated one of your exes?

• Is there anything illegal that you have done?

• Have you ever checked the phone in my absence?

• Would you accept the offer if some rich man offered you one million dollars and asked you to sleep with their wife?

• If you could marry multiple women, would you do it?

• What are your thoughts on sex without love?

• Is there anything in me that irritates you?

• Do you want me to change something in me?

• Who is the most good-looking person you have ever dated?

• Have you ever masturbated in public?

• Do you have any insecurities regarding any of your body parts?

• Have you ever left the house wearing no underwear?

You May Also Read: 335 Deep Personal Questions to Ask Your Crush

Conclusion

Love and sex go hand in hand. These dirty questions to ask your crush are all your need to up your flirt game. And it will raise the temperature of your room, no doubt!

How did your crush react to your questions? Did you guys have a hot-to-handle time?

Don’t forget to let me know in the comments!

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