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13 Flirty Questions to Ask a Guy You Like

by Sonya Schwartz

Do you feel like you suck at flirting?

Maybe you run out of things to say when you’re around a guy you’re attracted to?

Or perhaps you just have no idea how to subtly lead the conversation in a sexual direction? 

If you suffer from any of these problems, this list of 13 flirty questions to ask a guy will help you. These questions are great, because you can throw one at him whenever the conversation comes to a lull.

Almost instantly, you may notice a change in the vibe and a guy becoming more interested in you.  

However, before you go ahead and make a note of your favorite questions, I want to share an even more powerful concept to help you attract great men into your life. 

It’s based on a little-known aspect of male psychology that influences how they feel about the women in their life.  

It’s called the Hero’s Instinct, and I am so grateful that I discovered it a few years ago.

Once I learned how to activate this way of thinking in a man, I rarely had to worry about canned lines or gimmicks to make a man want me…

In fact, once you use this psychological trigger properly, it’s common that men may quickly begin to feel attached to you (read my personal story to learn more).

It’s simple to learn how to do this, yet so few women seem to know about it.   

If you’re hoping to make a lasting impression on a man, the best thing you can do is to discover how I learned to use the Hero’s Instinct

That’s not to say this list of 13 questions isn’t useful too, so let’s dive straight into them...

Flirty Questions to Ask Your Boyfriend

When it comes to keeping the spark in your relationship alight, it’s important to keep things fresh and interesting - especially when it comes to flirting. It’s all too easy to get stuck in a rut in your relationship, always doing the same things, eating at the same restaurants and flirting in the same way - if at all!

However, the following flirty questions to ask your boyfriend will help to spice things up and help to keep the excitement in your relationship alive, no matter how long the two of you have been together.

So whether you wait to try out your new flirting techniques in a new restaurant on date night, or simply try them out whilst the two of you are cuddling on the sofa - the following questions are sure to impress your boyfriend.

What’s the most exotic dream you’ve ever had about me?

Whether you’ve been talking about a dream you had the night before, or something a little more risquè, getting your man to open up to you about any dreams or fantasies he’s had about you is sure to add some excitement back into your relationship and get him to open up about any secret fantasies he might have.

Not only will this bring the two of you closer together - especially if your boyfriend finds it difficult to open up - but it will add a little bit of extra passion into your relationship and reignite that dwindling spark.

If you could have a hall pass for any celebrity, who would you choose to use it with?

If you’re a jealous girlfriend, this might not be the most appropriate question to ask your man, otherwise you’ll end up overthinking his answer and it might cause problems in your relationship, which definitely isn’t what you want!

However, if you’re completely secure in your relationship, then this is the perfect, cheeky question to spice up any conversation. Whether you’re watching a film starring his favourite actress, or he mentions a Victoria’s Secret model out of the blue, not only will this question put him on the spot, but it’ll also give you all the power to tease him later.

Is there a sexy scene in a movie you’d ever like to recreate together?

Whether you’re snuggled up on the sofa watching a raunchy movie scene, or it just comes up in conversation, this slightly risquè question is sure to get your boyfriend hot under the collar.

Not only will it make him think of his favourite sex scene from a movie, but it’ll also make him think about the two of you together - it’s a win-win situation, especially if you’re trying to spice up your relationship in the bedroom.

Have you been working out?

Picture this - the two of you are having a hug after a long day at work, your boyfriend has been lacking in confidence recently due to stress, so what better way to boost his confidence by asking him if he’s been working out?

Whether he’s been working out or not, this question is sure to make him feel amazing and earn you some extra brownie points, too!

However, there are a few occasions when you need to be careful about asking this question. If you live with your boyfriend and know where he is at most points in the day, then it might come across as you mocking him and make him feel insecure, which certainly isn’t what you want!

Additionally, if you know your boyfriend has been feeling insecure about gaining weight due to stress, injury or the holidays, then it’s probably best to leave this question alone and avoid drawing attention to his physical appearance.

Flirty Questions to Ask on a First Date

Flirting on a first date can be difficult. Not only is it nerve-wracking trying to work out if the person you’re on a date with is interested in you, it’s also hard to gauge the level of interest and just how much you should be flirting. It’s a lot to think about!

When it comes to having a successful first date, it’s important to be the best version of yourself, so if the thought of asking flirty questions fills you with dread, then it’s probably best to avoid them and stick to your usual date chat.

However, if you’re feeling super confident, the following flirty questions are sure to make your first date that little more interesting and help you to get a little bit closer to the guy you like - ensuring you get that all-important text from him after your date.

What’s Your Favourite Physical Feature?

If you want to subtly let the guy you’re on a date with know that you’re thinking about his body, then this is the perfect question for the job.

Seemingly innocent and breezy, this question not only makes him think about his own appearance (so you can find out exactly what he loves about himself), but chances are, he’ll repeat the question back to you - getting him to think about your body - all without you coming across as too forward or flirty. You master of flirting, you.

It’s the perfect flirty question to ask on a first date, allowing you to maintain your innocence while subtly driving him crazy.

Describe your perfect first kiss?

Be careful with this one, or you might just ruin your chances with the guy you’re on a date with! However, if things seem to be going well and all the signs are pointing to the fact that he likes you - and wants to kiss you - then this is the perfect way to give him the all-clear to go in for that first kiss.

If he’s been staring at your lips all night and you’re just waiting for the moment he leans in to kiss you, then this question is sure to give him the go ahead. Whether you initiate a flirty game of 20 questions, or wait until it miraculously comes up in conversation, asking a guy you’re on a date with to describe his perfect first kiss is sure to get things heating up between the two of you.

Not only will it subtly let him know that you’re thinking about kissing him too, but the anticipation of describing his perfect first kiss will make yours just that little bit more exciting.

However, if being forward isn’t for you, then you might want to stick to something a little more subtle.

What do You Find Most Attractive in a Potential Partner?

If you can’t work out whether or not your date is interested in you - or you simply want an ego boost - then this is the perfect, flirty question to ask on a first date.

If you’re a short brunette with brown eyes, and he tells you he likes tall, blue-eyed blondes, then you’ll know exactly where you stand (and exactly how shallow and narrow-minded your date is!).

However, if your date starts describing personality traits as opposed to physical features, then not only will you be able to establish that he’s looking for a deeper connection, but you’ll also be able to work out whether or not the two of you are compatible and if the date should end there or not.

What Are You Looking for in a Girl Right Now?

If you’re trying to establish whether the guy you’re on a date with is serious about getting to know you - or any girl - then this is the perfect question to help you find out.

His answer to this question will tell you everything you need to know about whether there’s any potential of a future between you. If he tells you he’s just got out of a long-term relationship, so isn’t looking for anything serious, then you’ll know whether or not he’s right for you. If you’re in the same position, then it’s the perfect situation, allowing the two of you to get to know each other without the pressure of wondering where it might go.

However, if you’re looking for something more serious, then you can conclude that he’s not for you. But if he responds telling you he’s looking for something a little more serious and just trying to find the right girl, then you might be onto a winner!

Even as a simple, non-invasive question, you’ll certainly find out everything you need to know.

Flirty Questions to Ask a Guy You’ve Just Met

Whether you’ve been set up on a blind date by one of your friends, or you’ve just bumped into a guy who’s completely your type in a bar - flirting with a man you’ve just met isn’t an easy task.

You obviously want to get to know him better without coming across as though your interviewing him, however, you also want to make sure there’s a little bit of flirting going on to gauge the level of chemistry between the two of you, all in a short space of time!

So if you’re stuck for flirty things to ask the guy you’ve just met, the following questions will help you to get to know him and work out whether or not the two of you have anything going on together.

What Brings you Here Tonight?

If you’re trying to establish whether or not the guy you’ve just met is single, or what he’s looking for, then asking him what he wants from his night out is the perfect, flirty question.

Seemingly innocent enough, asking this question will help you to establish whether or not you’re on the same wavelength without coming across as too forward.

 If he replies telling you he’s out with this girlfriend, then you know that this one’s a no-go. However, if he tells you he’s out with his guys and was hoping to bump into a nice girl, then that should give you the green light you need to continue with the conversation.

When are you Going to Ask for my Number?

If the two of you have been chatting for a while (and you’ve had a few drinks for courage!) then this is a great question to ask a guy you’ve just met to let him know that you’d be interested in taking things further.

Whether your friends are trying to get you to head to another bar, or you just want to let this guy know you’re interested, then asking him to ask for your number is a bold way to move things forward.

However, make sure you don’t come across as rude or arrogant when asking this one. It’s important that you’ve analysed the situation and worked out whether or not he’s actually interested in you before demanding that he asks for your digits. Just make sure your timing and delivery is perfect and you’ll be saving his number as ‘guy from the bar’ in no time.

Flirty Questions to Ask a Guy Over Text

If flirting with the guy you like fills you with dread, then texting him some flirty questions is the perfect alternative to trying it out in person. Not only does it give you time to think about what you want to say to him, but it takes away any of the awkwardness that can come across when flirting in person.

However, there’s just one problem with flirting over text - things can be easily misconstrued. What you think is an innocent, flirty text could come across as brash or over-familiar, which certainly isn’t what you want when you’re trying to impress a guy!

Whenever you’re flirting with a guy via text, it’s important to make sure you always triple-check your message to ensure it can’t be misinterpreted and ruin  your chances with the guy you like. Whether you add (or remove!) an emoji, or simply reword the text you were about to send - taking your time to think about a reply will only ever work in your favour and help you bag your Mr Right.

So whether you’ve met on a dating app, or you’ve been on a few dates before, the following flirty questions to ask a guy over text will have him hanging on your every reply and begging you to go on a date with him.

What’s Your Type?

Whether you’re looking for a confidence boost, or genuinely want to find out whether or not the guy you fancy is into you too, then this is the perfect question for the job.

It’s important to make sure you ask him this question when it’s relevant - if you text him this out of the blue, then you might come across in the wrong way. Instead, wait until the conversation naturally leads to something more flirty before you ask him about his ideal woman.

You’ll be able to tell from his response whether or not he’s interested in you. If he describes a woman exactly like you - or even includes completely personal traits of yours - then you’ll know that this guy might be one to pursue.

However, if his dream woman is the complete opposite to you, it might be time to get back on Tinder and find someone else to put your time into!

What’s Your Ideal Date?

Subtly putting the idea of a date into his head without him even knowing? It’s the perfect flirty question to ask a guy you’re texting.

Whether or not you’ve been on a date before, this question will let the guy you’re texting know that you’re open to going on a date with him, leaving it up to him to ask you.

Additionally, when it comes to your turn to plan a date, you’ll be super-glad that you asked him this, as you’ll be able to come up with the perfect date that he’ll never forget.

So next time you’re trying to think of a flirty question to ask him, you’d better not miss this one off your list or you might just regret it later down the line.

What’s Your Biggest Turn On When it Comes to Dating?

This is another question that signals that you’re open to going on a date with him, without being too forward.

Although it’s an innocent question, asking him what his biggest turn on is when it comes to dating will automatically make his mind wander to something more sensual - even if he doesn’t let on.

Additionally, if he tells you he’s got a weakness for a woman in red lipstick, or someone who offers to pay half the bill (even though he would never let them!), then you’ll have some clues as to how to impress him when he finally asks you out on a date. It’s a win-win situation.

It’s All in the Delivery

Of course, when it comes to flirting, it’s not just in the questions you ask, but the way you ask them - otherwise you risk coming across as rigid and shy. When you’re trying to flirt with the guy you like, it’s important to maintain a little eye contact, smile and position your body towards him - even lightly touching his arm or thigh if the moment feels right.

Eye contact is one of the most powerful tools you can use when you’re trying to flirt with the guy you like, and can make or break the situation, as it’s the primary way of showing interest in the person you’re talking to.

Whenever you’re asking a flirty question - or even when you’re waiting for a reply - you should lock eyes with your man for a few seconds, before playfully smiling and looking away to drive him absolutely crazy.

Additionally, it’s that all-important smile that will make him weak at the knees. Unlike other animals, humans bear their teeth as a friendly sign, and studies have shown that both men and women believe a smile is one of the most attractive features in a partner. Smiling completely opens up your face, making you seem more friendly, open and - most of all - attractive.

So next time you’re trying to flirt with the guy you like, don’t forget to flash those pearly whites - even if it is just for a few seconds.

Finally, when it comes to touching the guy you’re flirting with, it’s vital that you only do it when the time feels right - if do it too early and you might come across as too keen and make him uncomfortable, which definitely isn’t something you want to do.

Instead, when the time feels right during your conversation, brush your hand up against his forearm, resting it there for just a few seconds. Not only will the skin-on-skin contact make the two of you feel closer, but it will also signal to him that you feel safe and connected to him, generating a greater sense of intimacy between the two of you.

Sonya Schwartz
A hopeless romantic that struggled for many years to find her Mr "Right" and made all the mistakes you could think of while dating. Known for always choosing the wrong guys or messing up relationships, Sonya was finally able to change her approach and mindset when it came to dating which helped her eventually find the man of her dreams and become happily married. You can read more about me here...

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