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Dirty 21 Questions To Ask Your Crush

These dirty 21 questions to ask your crush are designed to bring the two of you closer together. Read more ⇣
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Written By Erica
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I'm Erica. I love to help people in their relationships and spiritual lives. I've been through a lot of ups and downs, and I want to share my insights with you.
21 Dirty Questions to Ask Your Crush

Dirty questions to ask your crush is something that will definitely bring the two of you closer together.

I know you’re probably wondering how on earth asking a question can help you guys get closer, but trust me it does.

When you ask your crush some sexy questions and they answer them honestly, it’s an automatic way to get them more attracted to you!

I’ve come up with 21 dirty questions to ask your crush. These questions should act as an ice breaker as well as bring you closer to your crush!

Make sure you also check out my list of 21 questions for a new relationship, and for adults.

How to play ’21 dirty questions to ask your crush’?

This is the easiest game to play and the only thing you need to do is be honest in your answers.

To make the game more interesting, players can divide up the questions and give them points. If a player answers all of the questions correctly they win.

Let’s get started …

Dirty 21 Questions To Ask Your Crush

1. How much do you like dirty talk?

This is a great question to ask since it’s a fun way to get them talking about sex and relationships. It gives you an opportunity to find out what they’re into and what their limits are. 

You can also learn how comfortable they are talking about sex in general and how open they are to discussing things like fantasies, fetishes, and other kinks.

2. How much do you like massages?

Asking someone “how much do you like getting massages?” is a good question, because massages are pretty great. 

As an activity, they’re personal and intimate in a way that doesn’t involve nudity or sex, but still feels very sexy. 

If you’re both into massages, it also makes for a perfect date night. You don’t have to get dressed up or leave the house, and afterward, you can get cozy together under the blankets.

Plus, if you know what kind of massage your partner prefers, this is another good opportunity to learn about each other’s likes and dislikes. 

Maybe your crush thought they loved deep-tissue massage — until their masseuse accidentally pinched their sciatic nerve. 

Now they hate all types of massages except aromatherapy with specially scented candles! In any case, this is an excellent way to find out even more about your crush before things get steamy.

3. Have you ever done it outside in the open?

This question will allow you to observe just how adventurous and daring your crush has been in the past! 

Most people aren’t open to the idea of doing it anywhere so if your crush says yes, you know that he isn’t the vanilla type of person when it comes to sex. 

In fact, this question will reveal that if and when you get together in the future, he won’t just settle for physical intimacy in the bedroom – but lots of other places!

4. Have you ever made out in a place you consider strange?

If you want to get close to someone, this is a great question to ask. A lot of people have not made out in a place they consider strange and will say no, but it’s the follow-up questions that are the most revealing. 

Some of the strangest places people have made out include public restrooms, movie theaters (while watching a movie!), at an airport, in an elevator, on a rooftop, and even in a car driving down the highway.

People who haven’t done something like this are probably more reserved than someone who has. This can help you understand how daring or reserved your crush is when it comes to intimacy.

5. How do you perceive quick sex?

By asking your crush this question, you will know how intimate or even romantic he can get in the bedroom. 

Some people are against quickies as they want to cherish every moment in the bedroom with the other person.

On the other hand, some people like it as it gives you a sense of adrenaline and thrill in the act of intimacy. 

So whatever your crush answers, you get an insight into what they like – and maybe you both share the same sentiment on this one!

6. How much do like sexting?

Sexting is a fun way to pass the time, and it can be a great way to get to know your crush. But sometimes it can be awkward and uncomfortable, especially if you don’t know each other that well yet.

It’s always a good idea to ask questions about your partner’s preferences when it comes to sexting. Does he like receiving sexts or sending them? Does she like texting about what she wants in bed? 

Does he want her to get down on all fours as soon as he gets home from work?

7. When last did you have a dirty dream?

This is another question that really gets down to the nitty-gritty of what your crush likes in bed. 

It also gives you an idea of how often they’re having dirty dreams — and whether or not those dreams are about anyone else but you! 

An intimate question like this one will help you gauge whether or not your crush has the same kind of desires as you do. 

If they’re comfortable answering it, they may even be willing to share some juicy details about their fantasy life!

8. When first did you have sex?

It’s a very personal question, but one that can tell you a lot about your crush’s personality. 

People who wait until they’re ready (or at least close to ready) and with someone they love will be more open and honest with their answers. 

They’ll also be more likely to consider how their answer affects others.

 On the other hand, people who have had sex before — even if it was in high school — may not want to admit that or may not want to talk about it. Either way, it’s information worth knowing.

If you aren’t sexually experienced and want to be, someone who can help introduce you to your body and what feels good for it. 

If that isn’t something you’re interested in, then find someone who also hasn’t had sex yet—or ever wants to have sex again.

9. What turns you on the most?

This is a good question to ask your crush if you’re looking for some naughty details. 

Whether they’re into getting kinky or they’re the type of person who likes to be romanced, this question will get them talking about what gets their blood pumping. 

Most importantly, it allows you to know how to flirt with your crush the right way!

10. Lights on or lights off?

“Lights on or lights off” is a great question to ask your crush. It’s relevant, light, and casual. This question is perfect for the person who wants to get to know their crush better but doesn’t want to seem too intense.

It’s also great because it can be answered in several ways, each of which gives you more information about your crush that you can use later in the conversation.

If they say “lights off,” they’re likely someone who likes to have some privacy. If they say “lights on,” they’re probably more open, confident, and transparent about themselves.

If they say “it depends,” then ask them how it depends — what does it depend on? Is it a mood thing? Do they want to feel comfortable? Or do they want to show off something special about themselves? 

A lot of times people just respond with this answer because they don’t really know what else to say and are hoping that it will end the conversation so they don’t have to come up with anything else!

11. What is the dirtiest dream you have ever had in your life?

Asking a question like this can be important for multiple reasons. It’s great to ask this because it will help you learn about your crush’s sexual fantasies and limits. 

This can be especially helpful if you are just beginning to explore sexual relationships with them. 

If they mention that they don’t want to have sex at all, then it’s helpful to know that before getting too invested in a relationship with them.

It is also good to ask questions like these when you are already established in a relationship as well! 

Maybe there are things you didn’t know about what turns them on or things that make them uncomfortable when thinking about sex. Being aware of their comfort levels and boundaries can only be insightful for you!

12. Do you have a favorite sex style and position?

This question is great because it gives you some insight into your crush’s sexual preferences.

If they say they like missionary, ask them why! Is it because that’s what they’ve seen in movies and TV shows? Do they feel like their partner should be able to see and talk to them while having sex?

If they say doggy style, ask them if it makes them feel more dominant or submissive! Although the doggy style is actually the most popular sex position across all genders, so maybe this isn’t such a weird thing to ask after all!

13. What sex style do you feel is overrated?

Why this is a great question to ask your crush? Well, it will be good to know what sex positions your crush dislikes. That way, you won’t do them when the time comes. 

If they say something like reverse cowgirl, it’s not that big of a deal because you can still do variations of that in other ways. It’s just helpful to know what not to do beforehand.

14. What puts you off most often as far as making out is concerned?

This is an important question because it can help you determine whether or not your crush has the same standards as you when it comes to physical intimacy. 

It’s also good to know what turns them off so that you can avoid any awkward situations later on down the road. Also, in case you and your crush potentially

15. Do you prefer cuddling more or making out?

This is one of the best questions to ask your crush. Why? Because you can learn so much about them by their answer. Are they more on the cuddling side and not interested in making out? That’s good to know!

But even if they say “I like both,” it’s still a great question because it helps you get to know the person on a deeper level. 

You’re going to learn what kind of physical contact they like, what kind of relationship they want with you, and whether or not you’re just meant to be friends. It also gives you an idea whether they’re romantic or not!

16. Do you have a sexual experience you feel was the worst?

If you’re feeling brave, you can ask them about their worst sexual experience. 

It’s a great way to gauge what they’re comfortable with, and it might even help you get some insight into whether or not they’re ready for something more serious with you.

If you want to ask a question like this, make sure that your intentions are good. You don’t want to come across as being nosy or creepy; just genuinely curious.

You should also be prepared for the answer that they may not want to talk about it. If they don’t feel comfortable answering the question, respect their decision and move on.

17. What are your views on friends with benefits?

Friends with benefits—in other words, sex with a friend.

The reason why I think that this question is a great one to ask your crush is that it will help you get a better understanding of how they think and why they do what they do. 

It can also help you figure out whether or not they are looking for something serious or if they want to remain casual for now.

18. Have you ever tried it in the car?

This is a great question to ask your crush because it can be a great way to get them to open up about their past. 

It allows them to share intimate details about themselves that they may not be comfortable sharing otherwise. 

If they’re willing to share, you’ll know that they trust you enough to do so, which can be very telling of how things will go in the future.

19. Do you like it when someone pulls your hair?

This question is great because it can help you understand what your crush likes in the bedroom—and if you’re on a date, whether or not you should go back to their place! 

If they don’t like when someone pulls their hair, this is an easy way to figure out that maybe they prefer softer touches and slower sex. If they do like it, ask them if there are other things that feel good for them.

20. Do you have any fetishes?

Knowing what your crush is into in the bedroom can lead to a more satisfying relationship.

If you have a fetish, this is a great question for you because it will let them know what’s on your mind, and hopefully get them thinking about their sexual preferences as well. 

It’s also a great conversation starter that might startle your crush or make them laugh – or both!

21. Have you ever had a one-night stand?

Simple, straightforward, and pretty revealing. If your crush has had a one-night stand before, they may be open to the idea of having another… with you. 

The best part about this question is that it also allows you to better understand your crush’s personality by hearing their answer and seeing how they react when they ask you the same question.


All of these dirty 21 questions to ask your crush are designed to help increase your chances of building a connection with your crush. 

Even if you’re not at the point where you want to ask them out right now, you can use these questions to gain insight into the person you’d like to be with in the future.

You should also check out my list of freaky questions to ask your boyfriend over text and questions to ask your crush while texting.

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