50 Flirty Questions to Ask a Guy

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When you’re first dating someone, flirting can be the best part. It’s so fun to get to know your date and have a bit of back and forth banter. Often, the conversation flows easily, but sometimes it doesn’t, especially if you’re chatting via text or if you’re just getting better acquainted.

But you like this guy, and you want to get to know him, and be a bit flirty in the process, right? Well, we’ve got the answer to your dilemma: a collection of flirty questions to ask a guy that are sure to get things sparkin’.

The first group of questions are great to ask a man you’re dating or interested in (and most of them work for women, too). While these are fun and flirty questions to ask a guy, they don’t get too risqué. You’ve got time to discover all those exciting things about a potential partner. For now, it’s all about the simple, carefree flirting. 

Want to go deeper and get a little flirtier with your questions? The next two sections will be perfect for you. We’ve divided the questions into 3 levels, based on intimacy and closeness of a relationship. Feel free to choose whichever questions you’re comfortable with, but for the purpose of going from sweet to sassy to sexy, we’ve divided into Crush Level, Boyfriend Level, and Husband Level questions.

The first options are perfect for flirting with your crush. Ideal when you’re trying to get to know a new guy. The 2nd and 3rd levels take it further, getting progressively more intense and sexy as we go. Those are great for flirty questions for married couples or for those in a serious relationship. 

Looking for deeper questions or more romance-related questions? Check out our massive list of 150 conversation starters for couples, with tons of options that are not quite so flirty.

But for now, are you ready for your perfect list of flirty questions for him? Let’s go!

20 Flirty Questions to Ask Him – Crush Level 

Ask these 20 questions of the guy you like. You’re sure to get some fun answers and have a good time learning more about him.

Do you like when women make the first move?

This is a great, innocent question to ask a guy you like. It also might give you the confidence necessary to be the girl to make the first move.

What physical feature do you find most attractive in a woman?

Chances are, the guy you’re flirting with is going to mention a part of your body that he finds particularly lovely. This is a sneaky little way to find out one thing he likes about you. 

What’s your biggest turn on in a potential partner?

This is a flirtatious question that definitely does not need to be physical in nature. And more than some of the other questions on the list, this one dives a bit deeper. What does your guy look for in a woman? How would he describe his perfect girl? This is a nice way to find out what he prioritizes in a relationship, and see if you two have compatible values. 

What are your most attractive qualities, physical and non-physical? 

Give your guy a chance to brag about himself here! This is also a fun question because you get some insight into his self-confidence and self-perception. Interesting stuff!

Do you believe in soulmates or love at first sight?

What does he think about real love? Does he think soulmates are a myth? What does he think about all these big questions? This doesn’t need to be a deep discussion, necessarily, but it can be a fun ice breaker or even a first date question. 

When are you going to ask me out?

If you and the boy are just texting so far, this is a fabulous flirty question to surprise him with. And it might just get things rolling along a bit sooner, giving him the confidence to finally ask you out!

When am I going to find out what it’s like to kiss you?

Another one in that same category. (These two questions make great flirty texts for him). You get the heat rising a bit with this one, and start him dreaming about how your lips are going to feel against his. 

If you could take a girl to any place in the world, where would you go?

This question combines two of our favorite things: love and adventure! Discover what kind of explorer your guy might be and what5 kind of vacations and destinations interest him. This is a great opportunity to talk about some things the two of you might do together in the future. (See our top date ideas for couples).

What are your biggest turn-offs?

It’s very telling to find out what a man isn’t into, as much as what he is. Often, his turn-offs may point to problems he’s had with exes, too. 

What’s the worst date you’ve ever been on?

This question is sure to bring some laughs as he relates his most cringeworthy date night. Be a sport and share yours as well—it’s only fair! You can also ask this on a first date as a fun wat to break the tension a bit. 

Would you rather kiss in the dark or kiss in the rain?

This is just a fun, flirty would you rather question that lets him start dreaming of you a bit more.

Who is your #1 celebrity crush?

Spill the tea, bruh. Who does he crush on, and why? 

What is something surprising about you?

Give your guy a chance to reveal something surprising and unexpected about himself. It’s cool to see what he shares, plus you’re bound to learn a fascinating little nugget about him. I’m guessing this information will only make you like him more!

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

Swap stories about when you’ve gotten wild in the past. This could also be a good way to see if he’s, you know, been in trouble with the law. JK! Sort of. 

What were you like in high school?

It’s not always fun to look back at those ancient high school days (well, ancient for us in our 30s and up), but it is a window into the past. Personally, I think it’s fascinating to hear how much he has changed since those days. 

What’s your favorite thing about me?

Give your dude a direct invitation to flirt unabashedly. Asking him what his favorite thing about you is can be a little intimidating, but it’s also a cute way to get him to open up about why he likes you. 

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

This is a flirty question for a man that demands he get a little vulnerable, but I think that’s an important part of getting to know someone. Is he able to open up to you? Not everyone shares easily, but it’s informative to see how willing he is to share a tale of him when he wasn’t at his best. 

What was your first kiss like?

More kiss talk. It’s never a bad idea to get him thinking about kissing you, so talking about past smooches can sometimes do the trick. A good followup question: what’s your favorite way to be kissed?

What is the most romantic thing you’ve ever done for a girl?

Discover a bit about the romantic side of your boyfriend (or potential boyfriend) with this flirty question. Not only do you get a peek at his previous relationships, you get to see what he considers romantic. You might also help him out by tossing in some hints about what you yourself find romantic. 

If you could change one thing about yourself, what would it be?

What does he choose? The answer might surprise you. PS: This is a great opportunity to let him know what you like about him!

15 Flirty Questions to Ask – Boyfriend Level

You can always pose these questions to a guy you like, but they are definitely on a more risque level, so tread carefully!

Where is the craziest place you’ve gotten frisky? 

Without getting too intimate, this question allows you to get the conversation a little bit more on the wild side. You’ll also find out a lot about your guy from his answer. 

Have you ever been caught in the act? By whom?

This is one of the most fun questions to ask as it gives you an inside look at his reactions to unexpected situations.

What’s the raciest dream you’ve ever had?

Another saucy question, this one might not be easy to ask when your relationship is really new, but as you start getting to know a guy better, this is a really fun flirty question to ask him. But be prepared to answer if he asks you the same one back!

What is your favorite time of day to have sex?

Does he prefer making love first thing in the morning? Or in the dark of night?

Where is your favorite place to be kissed on your body?

Find out what he likes the most and what he most wants you to do. 

What did you think of me when we first met? What was your first impression of me?

This is a great thing to ask a guy when you’ve been together awhile and are comfortable talking about those early days of your relationship.

Have you ever had a sexy dream about me?

Most of us really like to hear when our partners are thinking of us in their dreams, especially in a sexual context!

What is your favorite song to get down and dirty to?

What tunes make him want to jump right into bed? 

What was the worst part of your last relationship?

This question always offers interesting insight into a partner or potential partner.

What does the ideal relationship look like to you?

This is the best thing you can ask a partner, particularly if you’re looking to deepen your relationship and improve any problem areas. 

Do you like dirty talk, or do you prefer things to be more romantic?

This is one of my favorite flirty questions for him.

What can you tell me about you that you’ve never told anyone else?

Make sure you’re at a place where your man feels comfortable opening up to you with this kind of thing. This can be a tough question!

What is your biggest fear?

This might seem like an unusual addition to the list of flirty questions, but it’s one that will definitely help you get to know your man on a deeper level. 

What is your craziest ambition?

Here’s another question that provides insight into your partner’s dreams and goals. 

What is the hardest thing you have ever done, physically or mentally?

Give your man a chance to brag and also to share difficult challenges he’s been through in the past.

15 Flirty and Dirty Questions to Ask – Husband Level

With these flirty questions to ask a guy, things are starting to get a bit more scandalous! Let’s get right to it.

What is the hottest memory you have of us together?

This question will always deliver special answers, and you’ll get to reminisce together about a good time. 

What is something you’d like for us to try in bed together?

Open up the table to find out what it is your husband wants. 

Do you think there is anything you wouldn’t want to do in bed?

Everyone has boundaries and limits. Where are your partner’s?

What do you think my secret fantasy is? Would you want to help make it come true? 

With this one, your guy gets to guess at what you fantasize about. It’s fun to see what he guesses, and if he chooses right, it just might be something you two can plan to do soon.

When are you most attracted to me?

It can be nerve-wracking to ask a guy this question, but if it’s someone you love, I’m pretty sure you will be thrilled by the answer!

What is your favorite thing to do to me?

What does he love doing for you? More of that kind of thing, I think!

What’s your record for number of consecutive sessions in bed? Want to try and beat the record?

Being able to go again and again is a sexual goal, but it is not for the faint of heart! Are you two willing to try? Stay hydrated, friends.

What is the hottest sex scene you’ve ever watched in a movie or television show?

This gives you a clearer idea of what kinds of things turn him on and what he finds hot.

Have you ever been handcuffed or blindfolded? Do you want to be?

It might be something your husband’s into. You may never know if you don’t ask. 

What is the dirtiest, most NSFW text you have ever sent or received?

It may be one he’s sent to you or to another person he dated. 

What do you think you’re best at in the bedroom?

Again, let your man brag a bit. And be sure to share with him what you think he’s great at, too!

Would you ever get it on in a public/semi-public place?

The answer may surprise you.

Would you want me to spend an entire day making you feel good?

Obviously, the answer is yes. The catch is, you get to be the one in focus on the next date.

What’s something you’d like to hear me say in the bedroom?

This gives your guy a chance to tell you exactly what he’d like you to say in bed. 

What makes you feel your most sexy?

Finally, find out what make him feel his best and most attractive. Perhaps you can recreate those conditions ASAP. 


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