Flirty Questions to Ask A Guy

Are you wondering what flirty questions to ask a guy to get him intrigued by you?

Flirting is an art form. And just like any art, it can be something you’re born with or you learn with practice. Whether you are going back into the dating scene after being single for a while or you want to pique a guy’s interest and make them more interested in you, you can ask a guy flirty questions.

The initial physical attraction might be there, but that attraction can only last for so long. You want to be able to create a good first impression and intrigue a guy enough so they would want to keep hanging out with you. It’s also a surefire way to spark their interest and build chemistry

If you’re looking to up your flirting game, then we got you covered! Check out our list of fun and flirty questions to ask a guy!

Subtle Flirty Questions

When most people think of flirtation, they imagine going all-out in expressing your desire for the guy. While there is nothing wrong with that, if it’s worked in your past relationships, but mastering the art of subtle flirtation is guaranteed to make him want you even more. It’s important to drop subtle hints that you are attracted but not completely giving it away.

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The more you do this, the more you linger on his mind. You want to leave an imprint on his mind so he is curious and craves more of you. If you want to achieve that, you can ask him any of these subtle flirty questions that are sure to land you a romantic date.

Here are subtle flirty questions to ask a guy!

1. Do you like when women make the first move?

This question is one of the best ways to drop subtle hints that you’re into a guy. By asking this question, you’re basically telling him that you are making the first move. It’s interesting to see how he responds to this question and you can play along with him until he figures it out (if he hasn’t already).

2. When am I going to find out how your lips taste like?

Some people might think this isn’t subtle, but it can be if you deliver it well. Ask him this question in a fun yet playful manner, so it does not seem too direct. He might laugh this question off! Or better yet, he could show you the answer instead.

3. What’s your favorite thing about me?

It takes boldness to be able to ask this question to a guy. But when you ask a guy this question, be prepared for his answer as it might not be what you expect. As an additional note, use this question only when you’ve had previous interaction with a guy so he has a point of reference to make aside from your physical features (unless that’s what you are trying to get out from him).

4. What is your ideal relationship?

This is another tricky question but one that could work with proper execution. Make sure you set it up in your conversation prior to asking this question to give it some context.

5. What’s your secret fantasy?

This is the epitome of the subtle flirtatious game. It’s a great question to ask a guy if you want to get inside his head and unleash that flirtatious side of him. Asking him this question also gives him a hint that you might be interested to fulfill that fantasy – if he lets you.

6. What is your best physical feature and why?

This question is more of a set up than anything else. But it’s also a great way to get to know someone and how they perceive themselves. Some men like to brag about their favorite features while others will try to be humble. Either way, make sure you follow it up with your own thoughts about your favorite physical feature in a guy (aka a subtle compliment).

7. Who’s your current crush?

You are asking this question not because you want to know the answer. But rather so you can get an idea of the type of girl he’s interested in.

8. How long do you wait before you make a move on someone?

This is your way of dropping hints on him that you’re interested. It can be a challenge, too. It’s a way to tell him (albeit subtly) that you will make the move if he doesn’t.

9. Are you good at massages?

Massages are a highly sensual experience. Whether he says yes or no, you can follow it up with an offer to give him a massage. You’re in luck if he agrees to it!

10. So… what do you wear to sleep at night?

This is another sensual question that you can ask him. It’s definitely a pretext for a more intimate conversation so you must be prepared to follow through with it.

11. What do you think about PDA?

This is one of the flirty questions that could potentially lead to either you or both acting on it as a response. Make sure to always read the signs he’s giving you.

12. What’s the worst pickup line you’ve used?

This is a subtly flirtatious question because you will be sharing a good laugh once he shares his answer. You can also give him a shot to try some of his pickup lines on you.

13. Do you prefer kissing in the dark or rain?

The masters of subtle flirtation ask these kinds of questions. You can follow it up with a dare to kiss him (either in the dark or under the rain, whichever applies) – if you’re daring enough to try!

14. What is your love language?

This is an important question to ask because it provides you with an insight to the type of guy he is, especially if you are keen on building a happy and healthy relationship with him down the road. It can also give you hints on how you can win him over by giving him what he wants.

15. Would you consider yourself a romantic person?

Admittedly, not all guys are natural romantics. Therefore, pay close attention to how he responds to this question. It will also give you some ideas on how you can woo him.

16. What’s the most romantic thing you’ve done for a woman?

Again, not all guys would consider themselves as a romantic person. But it’s guaranteed that every guy has done something romantic for their partners before. Give them a chance to talk about that grand gesture and prepare to swoon.

17. What is your idea of a perfect date?

This is another question that gives you a chance to pick his brain. It’s your chance to plan your first date, if you ever get to that point.

18. I like your scent. What are you wearing?

Let’s admit it: this is just a flirty excuse to lean in closer and smell him more.

19. What was your first kiss like?

The first kiss is always special and memorable, even for guys. As he describes it to you, give him the opportunity to envision that first kiss with you, too.

20. How can a perfect guy like you be single?

This is the perfect example of how you can give someone a compliment and flirt with them at the same time.

21. Can you describe your dream girl?

It’s basically a set up to get him to describe you…

22. If you could change one thing about yourself, what is it?

This might be a subtle and flirty question but it’s a great way to see how confident and self-aware he is. You can follow it up by sharing what you like about him.

23. Do you consider yourself a good kisser?

This question will surely up the ante when it comes to your flirtatious game. Reel him in with this question and he might be provoked to demonstrate it to you!

Cute Flirty Questions

Flirting is a game. Consequently, you should be relaxed, confident, and enjoying it. You can create the perfect atmosphere for cute flirtatious moments with a guy by asking him these questions.

1. What is the best physical feature that attracts you most in a woman?

A flirty question like this gives you an insight into what he is looking for in a woman, and if you ever have a shot at taking things to the next level.

2. Do you believe in love at first sight?

If he answers yes, then you’ve got a romantic person in your hands. Give him a chance to express himself by asking why (if he says yes).

3. Who is your celebrity crush?

More often than not, people try to find some semblance of their celebrity crush in the people they meet. You might be the same type as his celebrity crush – it’s worth a shot.

4. Do you like adventure or romantic dates?

This cute but flirty question will have him spilling his thoughts on why he picks the date of his preference. It will also give you something to look forward to – in case you go on that date!

5. If I told you I like you, what would you say?

This question will surely have you hanging onto every word of his answer. Don’t be afraid to go for it!

6. Do you have any tattoos?

This flirty question is basically your excuse to take a peek into what’s underneath his clothes.

7. Have you been working out?

Men love to be complimented for their physique, especially those who take good care of their bodies. It’s basically more of a compliment than an actual question.

8. What’s your favorite song? Can you sing it for me?

Most men love music and this question is a great way to establish a connection. If he’s musical, you could get serenaded on the spot!

9. Do you prefer cuddling or making out?

This is a sexy yet flirty question that will surely raise the heat in your conversation. You’ll never know when he chooses to demonstrate his answer.

10. Have you ever been in a hot tub with a girl?

This question is an excuse to dive into his wildest fantasies. You’d be lucky if he answers you will be the first one.

11. Do you prefer brains or beauty?

If a guy is into you, you’ll be able to tell based on the answer that he gives you.

12. What’s the craziest place you’ve been frisky?

This question will surely steer the conversation to the wild side. Be prepared for what you’re about to hear by asking this question.

13. Sweet or spicy?

This is an open-ended question that is meant to assess where his headspace is at. His answer could either be food-related or something more sensual like a kiss. It’s fun to discover what he picks!

14. Fast or slow?

This is another tricky question to know what he’s thinking about. Let him play along with this question however he likes.

15. How many people have you kissed?

It’s a bold question to ask but cute if you can time it perfectly. Who knows he might add you to the list!

Fun Questions

Flirting with a guy does not always have to be daring. It could also involve asking him fun questions that will give you both a good laugh. For some guys, the ability to make them laugh or have a good time is a serious turn-on.

You can shoot your shot with these flirty questions to ask a guy to set the tone for a fun conversation.

1. When are you going to ask me out?

This can be delivered as more of a joke than an actual question. You will be sharing a hearty laugh or he could take this as a challenge and ask you out on a romantic date. Either way, it’s a win-win situation.

2. If you could take a girl out on a first date, where would you go?

It’s an opportunity for him to create that perfect first date scenario in his mind. Look for hints that he imagines you on that date!

3. What’s the worst date you’ve been on?

This question is going to help you bond over laughter as he relives his cringe-worthy date. It’s only fair that you share your own worst date, too! It’s a great question to ask to ease the tension or as an icebreaker.

4. What’s the craziest thing you’ve ever done?

This question does not have to be relationship-related. Encourage your guy to share anything that he’s done that would be labeled as ‘crazy’. His answer will provide you some insight into his antics and discover a side of him that he might not let show.

5. What’s the most embarrassing thing that’s ever happened to you?

Everyone has their embarrassing story to share. This is a fun question to ask a guy as it’s another opportunity to swap stories.

6. Have you ever been to a nude beach?

This might be a daring question to ask, but it’s fun as long as the timing is right. You’ll never know what they would answer!

7. How many kids do you like to have in the future?

This question is something that some women might be afraid to ask as it can make them appear desperate. However, you can totally pull this off if the context is right.

8. What are your thoughts on one night stand?

This is another tricky question but as long as you have enough rapport with each other then you can get him to share his thought.

9. Are you an introvert or an extrovert?

This question is fun because it gives him the chance to share a little bit more about himself. It’s also beneficial for you so you know the right approach to use when talking to him.

10. Have you ever been caught in the act?

This question has a two-fold benefit. First, it lets you learn more about the guy. And second, it is an opportunity for you to assess how he responds to unexpected situations.

11. What is your favorite part of the body to be kissed?

Make a mental note of his answer for future reference.

12. Who is your favorite fictional character?

It could be from his favorite movie or TV show. You can then share yours and it will spark up a conversation where you discover similar hobbies or interests.

13. Do you prefer to stay in or go out?

Depending on his answer, there are so many different ways that your conversation could go.

14. Shower or bath?

Add this to the list of open-ended question you can ask to flirt with a guy.

15. Summer or winter?

This is a fun question that provides insight to his personality. It can also clue you in on what he’s like and what he enjoys doing most.

First Date Questions

The flirty questions you ask a guy are different when you are on your first romantic date. It’s still too early to know if you will end up in a healthy and happy relationship. The first date is the official step towards getting to know each other.

Unlike the first interaction, you know a bit more about the person based on past conversations. The flirty questions you ask on your date provide an opportunity to dig deeper and to see just how compatible you are.

Below are the flirty questions to ask a guy on your first date.

1. What is your biggest turn on in a potential partner?

Since you are on a date, it only means that he’s interested in you, too. Asking this question gives you the opportunity to understand what he is looking for in a serious partner. Understanding what he prioritizes in a relationship will enable you to see if your values are compatible and how you can showcase that you are a good fit for what he is looking for.

2. What non-physical qualities attract you the most?

This question is flirtatious but substantial. The goal is to know what he is looking for in a partner that goes beyond the physical attraction.

3. What is your biggest turn-off/s?

Knowing what a man isn’t into is more telling than when you ask him what he is looking for in a partner. Therefore, apply the concept of reverse psychology to get that information out of him.

4. What’s the most surprising thing about you?

Most people have secrets and it takes a lot for them to open up to others about those secrets. You can ask a guy this question to see if he trusts you enough to open up. If he does, that could indicate that he is comfortable enough in you to share.

5. What were you like in high school?

Most people have their funniest childhood memory during their high school (or earlier) years. Use this opportunity to see a different side of him and share a good laugh at the same time!

6. What’s your favorite childhood memory?

Speaking of childhood memory, you can lead on to this next question. It would be heartwarming to hear his story about those early memories. Not all men feel vulnerable enough to open up, especially on a first date. Consider yourself lucky if he does!

7. What is your dream job?

Even though it’s only your first date, asking serious questions like this one is a great way to get to know them as a person. It can be just as intimate when a person talks to you about their future plans and what their goals are in life.

8. What is the best relationship advice you got?

This question offers a glimpse of his view of relationships and how he values them. Not everyone likes to get advice from others, but it’s an indicator of his willingness to learn when he does take them to heart.

9. What is your favorite movie?

This flirty question could be a subtle invitation for him to have a movie night, whether at the cinema or at home. Give him the opportunity to invite you over for a movie date night!

10. What was your last relationship like?

This is a serious question but also shows your interest in him. By understanding past relationships, you can learn from them and find ways to make sure that they don’t end up in the same path. It’s a flirty question that will show him your sincerity and genuine interest.

11. How do you like to spend your weekends?

Give him the opportunity to invite you for what he’s planned. In case he does not have any plans yet, you can make them together.

12. What was your first impression of me?

This question invites him to give you a compliment. At the same time, it allows you to analyze what features or personality traits you have that drew you to him.

13. What is the one thing you want me to do to you that I haven’t done?

To close it off, this question is sure to take your conversation to the next level. Depending on where his head is at, you might be surprised with what answer he gives you. Make sure to buckle up!

In Conclusion

Meeting a new guy or dating someone for the first time is always tricky. You are still in the getting-to-know phase so you have lots to learn about each other. Asking the flirty questions such as the ones suggested here is a great way to break the ice and cut the tension.

However, you need to be cautious about what and when you ask these questions. Every relationship has a different dynamic. Every guy is also different in terms of personality. Some guys will respond well to more direct and intimate questions while others respond well to the more personal ones. Make sure you assess the situation and how much previous interaction you’ve had to determine the right questions to ask.

The worst thing that you could do is to become too upfront with a guy with your flirtatious moves that you end up pushing him away. Also, it is worth adding most of these questions are designed for face-to-face interactions so you should never use them for sending flirtatious texts. The former gives you the opportunity to assess a guy’s reactions whereas a text won’t give you that luxury.

Also interested in women? Read our article, Flirty Questions to Ask A Girl.

Truly understanding Flirty Questions to Ask A Guy could mean the difference between great happiness and misery down the line. Find a psychic medium near you today, whether you’re in New York City, Chicago, Utah, Seattle in the US, or somewhere completely different, you can get the expert guidance you deserve. Don’t forget you can also get a psychic email reading at low cost, or try the best online psychic reading sites  such as Kasamba, Oranum, PsychicOz, Bitwine, Everclear Psychic and more.


Frequently Asked Questions

What is a juicy question to ask a guy?

A juicy question you can ask a guy must involve anything about sex or intimacy. For men, it is a crucial part of any relationship so they want to know if you have sexual compatibility right off the bat.

What are some flirty questions?

You can refer to the list of flirty questions to ask a guy that are listed above. They have been separated into different categories so you can determine the best fun questions to ask depending on what stage you are in the flirtation game.

How do you play 21 questions flirty?

The 21 questions game consists of asking a guy rapid but fun questions in an effort to get to know them. You can turn to this game if you’re out of ideas on what to ask a guy on your first date.

What questions do guys like to be asked?

It depends on the guy. However, most guys like to be asked substantial questions that are deeper than flirtation. Make sure you make an effort to get to know them a bit better, too.

How do you flirt with a guy through text?

Flirting through text can be done in a variety of ways. You can ask them how they are doing, how their day was like, or ask them playful questions. Every interaction is unique as it depends on the dynamic of your relationship towards each other (such as how long you’ve known each other and what’s your previous interaction was like prior to the exchange of texts).

What are some examples of flirting?

There are several ways that women can flirt with men such as making a prolonged eye contact, shooting brief glances at them, teasing them, or giving them subtle compliments. It varies based on the circumstances of the interaction between a man and a woman.

What compliments do guys like?

It depends on the guy. Some guys like to be complimented on their looks while others like it when women trust them to take care of her. It’s called the hero instinct and it makes men feel more masculine in a romantic relationship.

Do guys like when you flirt?

In general, yes. Men are drawn to women who flirt because it gives them the assurance that a woman likes them. It also makes the getting-to-know stage a bit easier. Men definitely like it when they don’t have to do all the work. It allows them to focus on having fun and getting to know the woman better.

Lucius Nothing

Lucius has been slinging tarot cards professionally since 2014. He’s taken the tarot to places most wouldn’t think of: His best-known patrons include Torture Garden, The Dark Circus Party, Handel & Hendrix, A Curious Invitation and The Candlelight Club, where he has been resident tarot reader for the past half-decade. His writing on divination, magic and creativity has been published in Sabbat Magazine and on Medium.


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