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255 Dirty Random Questions to Ask a Guy You Like

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Are you crushing on a guy whom you have just started talking to and want to know better? Or are you already into a steady relationship and want to spice things up?

Whatever situation you are in, the best thing that you can do to know the person you like is to ask him questions! So yes, you have to come out of your shy self and take things into your own hands.

When you ask questions, you get to know a lot about him – his likes, his dislikes, his sexual preferences, his past experiences, what kind of relationship he would like to have in the future, what type of women he feels attracted to, what he would do in certain circumstances and more – the list is never-ending!

You know, when I started dating back in my college days, I used to ask my boyfriend a lot of questions because I wanted to know EVERYTHING about him! And trust me, it helped so much in growing our relationship from strong to stronger and then the strongest that we are married now!

Don’t worry, thinking what he will think about you. Most guys enjoy dirty talks, and when you ask them seductive questions, they get turned on.

And the best part? You will end up knowing him better. Isn’t that what you want?

Now, are you having trouble selecting the questions you want to ask your guy? How about a little help?

I have listed some random questions to ask a guy. The questions are flirty, seductive, sensual, and whatnot – perfect for all the stages of a relationship. All you need is to go through it and see what suits your situation the best.

Dirty Random Questions to Ask a Guy You Like About His Choices

Dirty Random Questions to Ask a Guy You Like About His Choices

If you like a guy, it becomes important for you to know about his choices and his preferences, isn’t it? After all, you don’t want to blow it doing something that he doesn’t like! So, ask him these dirty questions and see how he responds.

  • What is your preference: handjob or blowjob?
  • What turns you on more: a mini skirt or tight jeans?
  • What do you like to wear more: briefs or boxers?
  • Do you like it if your partner laughs while doing it in the bedroom, or do you like to stay serious during the act?
  • Suppose you are on a blind date. Will you make the first move, or would you like the girl to make the first move?
  • What about your thoughts on love bites? Do you like to give it or receive it more?
  • What, according to you, are the best places to receive love bites?
  • How do you like your girlfriend to be – all-natural or shaved?
  • What do you prefer more – rough or sensual?
  • What are your thoughts on oral sex? Do you like to give it more or receive it more?
  • What kind of bedroom environment do you like? For example, do you like to turn some music on in the background? If so, what kind of music?
  • What is that part of your body that makes you turn on instantly when a girl touches it?
  • Are you an early morning or a late-night person?
  • Do you have sex dreams often?
  • How often do you take things into your own hands?
  • Do you like it loud, or do you like to keep things silent?
  • Are you a butt or a boobs guy?
  • What is that part of the women’s body that attracts you the most?
  • Suppose you are given a choice to choose between oral sex and vaginal sex for the rest of your life. What would you choose?
  • What is that part of a woman’s body that turns you on the moment you see it?
  • What is sexier to you: lips or eyes?
  • Do you prefer bold lips or winged eyes?
  • There are so many things that you can do in the bedroom, right? What is your top pick among all of them?
  • Which side are you on – beauty or intelligence?
  • What would you like to see your girl in?
  • What kind of kiss is the best kiss according to you?
  • Do you like to talk to your partner while having sex, or do you like to stay silent?
  • Where do you like to do it – in a hotel room or your home?
  • What do you prefer more: a sex marathon or a quickie?
  • What kind of hair do you like on women – short or long?
  • What kind of girl turns you on: short or tall?

Excitingly Dirty Random Questions to Ask a Guy

Excitingly Dirty Random Questions to Ask a Guy

Do you want to excite the guy you like? Do you want to make things heated up between the two of you?

Ask him these naughty questions to have a great time!

  • How often do you watch porn?
  • What type of porn makes you hard?
  • How many times in a day do you think of having sex?
  • What are your thoughts on gay couples? Do they turn you on?
  • Do you watch gay porn?
  • Do you watch lesbian porn?
  • Are you into erotic fiction? Do they turn you on?
  • Do you like to talk to your partner and call her various names while you are having sex?
  • What was the longest that you have lasted without sex?
  • Can you stay a month or even a week without having sex?
  • Do you like to talk dirty?
  • How dirty can you talk? Give me some examples
  • Have you ever followed any page on sex on social media?
  • Have you ever read something about how to increase your libido and have applied it in real life?
  • Are you into medicines that can increase your libido?
  • Have you ever tried anything that can make you last longer in bed? If so, what was it?
  • Have you ever used a condom that got torn during the act?
  • Do you like it when a girl makes the first move?
  • How often do you like to have sex?
  • Name that one sex position that is your hot favorite?
  • Have you ever tried a sex position that you saw in some magazine but failed miserably?
  • Have you ever got hurt while having sex?
  • What is that one sex position that you are a pro at?
  • Have you ever laughed while having sex?
  • Is there any position that you don’t like at all?
  • Is there anything that you don’t want to do while you are intimate with someone?
  • What is the stupidest thing that you have ever done to catch the attention of a girl?
  • How far would you go to make a girl fall for you?
  • How many one-night stands have you had?
  • Have you stayed in contact with any of your one-night stands?
  • Do you like having one-night stands, or are you more into one life, one girl thing?
  • What is your best sexual experience to date?
  • Would you like it if your partner called you names while doing it?
  • Is there any specific kind of sex that you would like to do again and again?
  • What was the worst sexual experience that you ever had?
  • Have you ever tried to copy a sex scene from a movie and implement it in real life?
  • What is your favorite sexy scene from one of your favorite movies?
  • Have you ever had drunk sex?
  • Have you ever had a drunk kiss?
  • Do you like it when you are drunk?
  • Have you ever had a fantasy in which you were doing it with a celeb?
  • Have you ever accidentally seen someone doing it?
  • Is there any place where you haven’t done it but want to do it in the future?
  • What is your favorite public place where you would like to do it someday?
  • Do you like to do it in public places?
  • Have you ever got caught while doing it?

Also Read: 264 Daring Truth Or Drink Questions For Couples

Random Questions to Ask a Guy About Online Sex

Random Questions to Ask a Guy About Online Sex

Now, in this age of technological advancement, we all spend quite a lot of time in front of the screen. Agree?

This makes questions on online sex something that you really want to have answers to.

  • Would you like me to send you a dirty picture of mine now?
  • Have some unexpected person ever sent you dirty texts?
  • Have you ever received a naked picture of a girl?
  • Have you ever sent a naked selfie to someone?
  • What are your views on sexting? Do you like it?
  • Do you like to initiate sexting, or do you like your partner to initiate it?
  • Have you ever had sex on your first date?
  • Would you share your bed with someone you met on some dating apps?
  • What are your thoughts on phone sex? Have you ever tried it?
  • Have you ever mistakenly sent a nude of yours to your parents?
  • Have you ever mistakenly sent a dirty picture of yours to someone you would otherwise never?
  • Have you ever created a fake profile of yours on social media just to talk dirty with girls?
  • Do you have any profile on some dating site where you can chat anonymously?
  • What would you do if I sent you a nude right now?
  • Have you ever had a sex chat with someone you just met on social media?
  • Have you ever cum by phone sex or sexting?
  • Can you send me a hot picture of yours wearing nothing?
  • What is your favorite body part of yours? Send me a picture of it. I want to see it too
  • Have you ever fantasized about having sex on an isolated island?
  • Have you ever sent a nude to your partner when she is with her family members?
  • Have you ever sent a dirty text to a girl in a public place just to see her reaction?
  • What is your worst experience of asking someone to send nudes?
  • Does my text make you smile? If so, you have to hug and kiss me

Random Sensual Questions to Ask a Guy

Random Sensual Questions to Ask a Guy

How about turning things hotter and making your guy sweat?

These are some random questions to ask a guy that are sure to increase the heat of your conversation!

  • What is your favorite place in a woman’s body that you want to kiss the most?
  • Some people love to do it in the rain. Are you one of them?
  • Do you like to experiment in bed?
  • Do you want to taste my lips and see if it reminds you of something?
  • What is that one place that you would love your partner to touch you?
  • Do you want to play the game of seduction with me?
  • How do you feel when you see couples making out? Does it turn you on?
  • Do you like to make out with your partner in public?
  • To what extent can you go in public?
  • Do you generally get exhausted after round one, or are you always ready for a round two?
  • How many times can you cum in one night?
  • Do you like to look into your partner’s eyes when you do it, or do you not like to have eye contact?
  • Are you more into kissing or cuddling?
  • Do you like to cuddle for some time after you have cum, or do you become so exhausted that you go to sleep?
  • How important is foreplay to you?
  • Do you foreplay for quite some time before you do it or dive straight into it?
  • Do you like foreplay? What is your favorite kind?
  • How do you like to get kissed?
  • What if you see a woman eating something in a seductive way? Does it make you hard?

Bonus Read: 11 Definitive Signs He Sees Himself Marrying You

Dirty “Have You Ever” Questions to Ask a Guy You Like

Dirty “Have You Ever” Questions to Ask a Guy You Like

When I think of ‘have you ever’ questions, I find so many random questions to ask a guy! And you know, this is the best way to know what the person is like when it comes to intimacy.

  • Have you ever faked an orgasm?
  • Have you ever given a sensual massage to your partner?
  • Have you ever thought of taking a video of your partner and you while you are at it?
  • Have you ever had sex with a random person?
  • Have you ever gotten drunk and done it with some stranger?
  • Have you ever done it while other people were watching you?
  • Has your partner ever given you a handjob while you were driving?
  • Have you ever gotten into a one-night stand with someone who was already engaged or in a relationship?
  • Have you ever cheated on your girlfriend?
  • Have you ever got cheated on by someone you loved?
  • Have you ever given orally to your partner?
  • Have you ever seen yourself in the mirror while having sex?
  • Have you ever masturbated in front of someone?
  • Have you ever masturbated when you were at your relative’s home?
  • Have you ever kissed someone that you regret now?
  • Have you ever had sex in the toilet of an airplane?
  • Have you ever masturbated in a washroom that was meant for public use?
  • Have you ever dated someone whom you had a one-night stand with?
  • Have you ever forgotten to use a condom while having sex and then tried to use it while you are at it and failed to do so?
  • Have you ever used lubricants while having sex?
  • Have you ever had sex with someone just because the other person wanted it?
  • Have you ever tried BDSM?
  • Have you ever had a submissive?
  • Have you ever been in a relationship just for sex?
  • Have you ever played sex games with your partner to spice things up?
  • Have you ever used a sex toy?
  • Have to ever had sex with two women at the same time?
  • Have you ever had sex with someone while thinking about someone else?
  • Have you ever been to a strip club?
  • Have you ever done it on a beach?
  • Have you ever done it in your bathtub?
  • Have you ever had sex with multiple women in one day?
  • Have you ever been caught while doing it somewhere it was not allowed?
  • Have you ever had sex in the car?
  • Have you ever done it in the kitchen?
  • Have you ever involved food in your foreplay?
  • Have you ever masturbated more than four times in a day?
  • Have you ever done it with some ex of your friend?
  • Have you ever paid for it?
  • Have you ever done it while being blindfolded?
  • Have you ever had a one-night stand with someone elderly like your professor?
  • Have you ever practiced kissing using food?
  • Have you ever used a pillow to practice some positions?
  • Have you ever kissed one of your cousins or relatives and liked it?

Hot Questions to Ask a Guy You Like

Hot Questions to Ask a Guy You Like

Let me tell you something. Do you know how most guys love it when the woman they like ask them naughty questions or initiates a sexy conversation?

Well, now you know!

  • How do you like it – fast or slow?
  • Have you ever unhooked a bra successfully using just one hand?
  • How long have you been in physical relationships?
  • How many positions have you tried till now? Give me an estimate
  • How many sexual partners have you had till date? Count and say
  • How do you prefer ending a sec session?
  • What is the most romantic kind of sex, according to you?
  • What is the longest time that you have ever been doing it?
  • What are your thoughts on a threesome? Have you ever tried it?
  • How much would you rate yourself for satisfying your partner on a scale of one to ten?
  • Do you want me for one night?
  • Have you ever played the role of a dominant?
  • Have you ever done it without foreplay?
  • Would you like to have a taste of me on your fingers?
  • How much time do you need to cum?
  • How many times did you get compliments from your partner for giving them a great time in bed?
  • Have you ever eaten food from your partner’s body?
  • When you see your partner in wet clothes, do you get turned on?
  • What makes you hard the quickest?
  • How much tongue do you make use of during a smooch session?
  • On how many body parts of your partner have you used your tongue?
  • Do you like to touch your partner all over her body while kissing her?
  • Do you like to push her against the wall and play with her hair while kissing her?
  • Can you give me the chance to taste you?
  • What do you like the most – giving or receiving?
  • What is the one thing that turns you off the most?
  • Can you guess which body part of yours I like the most?
  • If I told you that I would like you to have you in my bed right now, what would you do?
  • How fast can you make a woman cum?
  • Do you like the lights on or off while doing it?

Flirty Questions to Ask a Guy You Like

Flirty Questions to Ask a Guy You Like

Flirting is an art. If you play your cards right, you never know to what extent you are going to take your relationship!

Here are some random questions to ask a guy for inspiration – perfect for the initial stage of a relationship.

  • Your lips look like they have no friends. Do you want my lips on them to make them feel like they have friends?
  • They say that you burn tons of calories when you kiss. Do you want some help in exercising?
  • What do you prefer doing if you want your partner to know that you are in the mood?
  • Apart from being hot, what job do you do?
  • What would you do if you found me answering the door wearing nothing?
  • Have you ever got compliments for your kissing style?
  • Are you good in bed?
  • Do you want a full-body sensual massage from the best masseur – that is me?
  • Have you ever had a naughty and steamy dream about me? What would you do to me if you would find me right beside you on your bed when you open your eyes?
  • What were you doing to me in your dreams? Can you show me?
  • Do you think your hotness can attract women?
  • What would you do if I touched you right now?
  • What do I have you touch you to get you turned on?
  • Would you like to put your hands under my skirt?
  • Have you ever been naked in public?
  • Are you a shy or a bold person when it comes to intimacy?
  • I like the color of your underwear. What color is it, by the way?
  • What, according to you, is that one piece of cloth that is the easiest to remove from a woman?
  • Have you ever used only your mouth to remove clothes from a woman’s body?
  • How much do you like to see me in sexy lingerie?
  • High boots or sexy heels – what attracts you the most?
  • I can’t get my eyes off your pants. But I think there is a problem with the zipper. Do you want me to have a look at it?
  • Have you ever fantasized about ripping my clothes off my body?
  • Would you like to have me for a whole day? I would permit you to do anything you want to me
  • My bed broke. Can I sleep with you tonight?
  • With tongue or without a tongue?
  • Is there a specific color of clothing that you get attracted to?
  • Would you dirty dance with me?
  • What is that one spot in my entire body that you are dying to kiss?
  • Which category do you fall – giver or receiver?
  • What are your favorite games to play in the bedroom?
  • Have you ever used toys on yourself?
  • Have you ever used toys on your partner?
  • How about you cuddle with me while we watch Netflix?
  • Can you guess what color bra I’m wearing? I will let you do to me whatever you want if you guess it correctly
  • Have you ever imagined what our first night would look like? Tell me in detail
  • Where do you want to get touched when we make out?
  • Has anyone ever told you how sexy you are?
  • What is the favorite memory that you have of me?
  • Would you like to go on a dinner date with me tonight?
  • How do you feel when you hug me?

Naughty Questions to Ask a Guy About Their Relationships

Naughty Questions to Ask a Guy About Their Relationships

When you like a guy, you want to have at least some knowledge about their previous relationships or what his life was like before he met you, right?

And that is perfectly fine! So here are some questions that you can ask him.

  • Do you like to have serious relationships, or are you okay with casual relationships?
  • Have someone older than you ever seduced you?
  • Were you ever in a relationship with an older woman? How was your experience?
  • Have you ever fantasized about your female colleagues?
  • How far can you go for the love of your life?
  • Have you ever fallen for your teacher?
  • Have you ever been in a ‘friends with benefits’ kind of relationship?
  • Have you ever had sex with someone for whom you had no feelings?
  • Are you still on talking terms with the person with whom you had the first sex of your life?
  • How old were you when you did it for the first time? Do you still remember what it was like?
  • What is the total number of exes that you have?
  • Are you still in touch with any of your exes?
  • Do you still have the numbers of your exes on your phone?
  • At what age did you have your first kiss?
  • If you were to compare me with the other partners that you had before, what would make me stand out?
  • How flirty are you? How much would you give yourself on a scale of one to ten?
  • Have you ever asked a woman to meet you somewhere so that you can make out?
  • Have you ever been in a long-distance relationship? Did you ever cheat your partner during that time?
  • How would you describe yourself in two words?
  • How would you describe your intimate life in two words?

 

Conclusion

So, this is my list of some random questions to ask a guy. And I have made the list in such a way that you can modify it according to your needs.

Happy questioning!

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