41 Flirty Questions to Ask a Guy You Like

So, you have a new crush. It is an exciting period. You have your own night texting sessions, awkward moments, and of course, lots of flirting. So, what should you ask? What should you say? …


So, you have a new crush. It is an exciting period. You have your own night texting sessions, awkward moments, and of course, lots of flirting. So, what should you ask? What should you say? How to keep the conversation going in a flirty way? We have your answers. We have compiled a list of flirty questions to ask a guy.

You can ask them when you start dating, or during the get to know part. It is all up to you, and how do you want to come up. Do you want to look flirty? Or you want to keep that part for the relationship?

Just remember, one of the least anxiety-inducing ways to handle a crush is by engaging in a flirty conversation. You will have fun, and you can learn a bit about your potential partner. Here are a couple of ice breakers.

What do you look for in people?

Go directly, and you will know if there is potential for a romantic relationship.

What do you want to do on dates?

See whether he wants more adventure, some serious talking, or just hanging out. If he says he loves going bungee-jumping or something similar, you have an adventurous type.

Do you work out? How often?

Men love to brag about their body and exercise routine. Throw him a bone.

What is your biggest passion?

This is another way to give him some time to brag. And you will also get to know him and his hobbies and interests.

Describe yourself in three words

This might sound cliché, but it is a classic. It works for job interviews, and it works for dating as well.

Describe me in three words

Again, it is a cliché. But it is a nice cliché. You get to know what he thinks about you.

What do you prefer, brains or beauty?

You will rarely hear a good answer here. Most men will admit they do not prefer beauty. But do not fall for it. We all want a balance of both.

What do you do over weekends?

This question will let you know whether you fit or not. Usually, the weekend is a time for spending time with the partner. During the week you might have more work, but the weekend is another thing.

What is your best feature?

See whether you consider the same features as well. The question will give you a chance to splash some compliments and make him feel more secure. Boosting his confidence will pay off definitely later on.

What is my best feature?

This will help you continue the stream of compliments. And you can tease him. Say he says your butt, wouldn’t that mean some sassy and racy comments and compliments?

What makes you smile?

We all want someone that can make us smile. And we want to have fun and laugh together, right?

Say you were an emoji, what would it be?

There is lots of potential here. Answers like kissy, smiley face, winky face, grumpy face, and more might come up.

Do you prefer the little or the big spoon?

Do you have a cuddler here? What kind of cuddly person is he? Can you two co-exist?

Tell me the perfect date for us two

Sometimes, you just want to play the direct game and see his response.

What was the first thing you noticed on me?

We all want to know what works. And what he did notice on you. This conversation starter is a great way to reveal more.

What do you look for in a partner?

The idea here is to determine what type of woman he wants. We have to warn you, if he gives classic and cliché answers, he hides something. But if his answers align with your personality and type, we have a winner.

What do you find attractive in a woman?

Again, your goal here is to see whether you two fit together. It will also give you an idea of his most important features and qualities.

What makes you attractive?

Or what are his most attractive qualities. The question allows him to put his foot on the gas. He can speak about himself, and communicate his strengths.

Am I your type?

If he answers no, follow up with why. How come? Does he often sticks with his type or not? Remember, love doesn’t stick to lists. And just because he has a type, it doesn’t mean he doesn’t find other women attractive.

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What is your favorite thing about yourself?

There are many ways to get him to talk about himself. This is one of them.

What is your favorite thing about me?

And after he brags about himself, switch onto you. See if he has the same passion in his tone.

What is your idea of a perfect date?

This gives you an idea of his expectations. But also, it makes him think more.

What turns you on?

When you want to take the flirting thing up a notch, start asking more risqué questions.

What turns you off?

Basically, you ask him what you shouldn’t do. Fun fact: this question will make him uncomfortable. And we love to put men in such positions.

Are you ticklish?

The trick here is to follow it up with trying to tickle him. This will give you a chance to touch him, and see how he reacts.

What is your favorite sexual position?

Do you know that the sexual position tells a lot about a man? If he prefers missionary, he likes to feel in control, but he also feels insecure. Doggy taps into his territorial animalistic instinct. If he prefers woman on top, he doesn’t feel smaller by letting you take control. And spooning reveals a passionate and romantic lover.

What is your favorite place for sex?

With these types of questions, you get your guy to think about sex. And that is a winning combination. You implant the idea there, and he might have a hard time controlling himself.

What is the craziest place you’ve had sex?

Do you want to know how sexually adventurous your guy is? Ask his question.

What do you consider a perfect kiss?

If you want your date to kiss you, just talk about kissing. He will definitely try to show you his perfect kiss. But remember, it might not come out as perfect the first time.

Do you want to take the lead, or you can follow in a relationship?

This question will help you determine his expectations. And it will help you understand whether you can work together. If both of you want to lead, you might bump heads eventually.

How many times have you fallen in love?

How old is your guy. Has he ever fallen in love? If not, that might sign a red flag. You probably deal with an emotionally unavailable guy.

If you could spend a whole day with me, what will we do?

Give him a chance to plan a full day with you. See whether he can make it out for 24 hours.  And it is a good indicator of his feelings for you.

What makes you crack?

See whether he admits some secrets or not. If he answers with some of his embarrassing secrets, he does trust you.

Do you have a celebrity crush?

No, you do not have to look like his dream girl. Do not sweat if you do not look like her.

What would you do if I kissed you?

Do you want to put guys in uncomfortable positions? This is it. They rarely expect the girl to make the move.

Do you have any fantasies?

Again, you do not have to make them happen. But it can help.

Where would you like to kiss me?

What does he answer? Your lips? Your neck? Or somewhere else. It will give you a good idea whether he is a romantic guy or more of a seducer type.

Have you ever fantasized about me?

Again, if you want to put him in an uncomfortable position, this is it. After all, you can make his dreams come true.

How would you seduce me?

Insist on a descriptive and detailed explanation.

What is the most adventurous thing you have done in bed?

See how he acts and behaves. Just remember, he might have had a monotonous relationship before. But if you are adventurous, he can adapt, don’t worry.

Where and when will we go on our next date?

Time to close out the conversation with something direct. If this is your first date, replace “next” with “first”.

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