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Whether you’re crushing, dating, or already married, flirting can be one of the best parts of a relationship! It’s so fun to have that back and forth banter. Often, the conversation flows easily, but sometimes it doesn’t, and that’s when you might want to have some flirty questions to ask a guy tucked in your back pocket!
You want to up your flirt game, right? The perfect collection of flirty questions to ask a guy is sure to get things sparkin’!
The first group of flirty questions to ask a guy are great for the man you’re dating or interested in (and most of them work for women, too). While these are fun and flirty questions perfect for both texting and in-person flirting, they don’t get too risqué.
The 2nd and 3rd sections take it further, getting progressively more intense and sexy as we go and are perfect for flirting in more serious relationships.
If you’re looking for deeper couples’ questions, this list of 150 conversation starters for couples is perfect for prompting thoughtful conversations with your partner.
Are you ready for a fun list of flirty questions for him? Here it is!
50 Flirty Questions to Ask a Guy – Crush Level
These 50 flirty questions for him are perfect to inspire some fun answers and have a good time learning more about your crush!
Do you like when women make the first move?
This will tell you exactly what you need to know when it comes to who will make the first move between you two!
What physical feature do you find most attractive in a woman?
Chances are, he’ll mention what he finds most attractive on you! 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 nice way to find out what he prioritizes in a relationship, and see if you two have compatible values.
What do you think are your most attractive qualities, physical and non-physical?
This is 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?
When are you going to ask me out?
This is a fun and flirty question that might just give 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. Sometimes a guy just needs a clear hint that you’re interested!
If you could take a girl to any place in the world, where would you go?
Discover what kind of explorer your guy might be and what kind of vacations and destinations interest him and could even segue into 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 cringe-worthy 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 way 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.
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?
This is a nice little window into his past. Personally, I find this kind of stuff fascinating!
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 might show you how comfortable he is with you. Is he able to open up to you? Not everyone shares easily, but his response is bound to give you some great info!
Who was your first crush?
This is a great opportunity for you to find out more about him and the kind of girl he tends to be interested in!
Do you prefer adventure dates or chill dates?
This one is going to give you some great information for date planning when you finally go for it and get to the dating stage!
How long do you usually like to get to know someone before you make the first move?
This is basically just an adorable little hint hint you can drop to let him know you’re wondering if he’s going to make the first move or not!
If I told you I think you’re cute, what would you say?
Okay, this one is pretty forward, but someone has to get the ball moving in the right direction!
Do you have a favorite childhood memory?
You can learn a lot about a person by asking them about their childhood! All info is good info, right?
I think it’s so sweet how you <insert sweet thing he said/did here.> Have you always been this sweet?
Flirty questions that contain a compliment are never a bad thing!
Are you good at massages?
Could be a good setup for a “why, do you want one?” response!
Sweet or spicy?
This is a great open-ended question that will at least let you know where his headspace is while talking to you… is he thinking of his favorite fast-food order, or is he thinking of how he wants your first kiss to go???
What was the happiest day of your life so far?
Another great getting-to-know-you type question!
If you could see the future, would you want to?
Learn a little more about how your crush thinks with this one!
So… what do you wear to sleep at night?
This might turn into a little bit of a risque convo about what he does or does not wear at night!
So what are your thoughts on PDA?
This could definitely be a good one to learn before you reach the relationship stage!
Do you know your Enneagram Type?
Learn your crush’s enneagram type, learn more about him!
Are you ticklish?
And if this leads to a “why, are you?” and a cute little tickle fight, well… that’s not a bad thing!
I love the way you smile/laugh/tease, how are you so adorable?
Let’s just go ahead and let him know how cute you find him, mmmkay?
Do you consider yourself more brains or brawn?
Be ready, because hopefully he’ll ask you for your opinion and give you the perfect setup to tell him he’s the perfect mix of both!
What is the funniest thing that you’ve ever had happen to you?
Learning each other’s sense of humor is so important! Find out what he finds funny with questions like these so you can tickle his funny bone later, too.
Do you have any tattoos?
This might lead to a fun game of peek-a-boo for you two!
If you won a million dollars tomorrow, what would you do with it?
This is always a fun way to learn what someone’s priorities are! Plus, maybe one of the things he’ll list will be “ask you out on an epic date night/hot balloon ride/exotic trip somewhere…”
Have you ever had a crush on a character from a movie or show?
Get a little more insight into his likes/dislikes with this one!
Have you been working out?
Let him know he’s looking good with this one!!!
What’s the funniest pickup line you’ve ever used or had used on you?
This will hopefully lead to some laughs! Have yours in mind for when he asks what yours is!
Do you know your Love Language?
This might require a little more explanation if he doesn’t already know what love languages are, but learning if he’s a words of affirmation guy, acts of service guy, physical touch guy, etc will be VERY helpful for you if you’re wanting to win him over!
Are you more into brains or beauty?
If he’s into you, he’ll probably find a way to answer this that also includes you… bonus points if the phrase “total package” come up!
Do you consider yourself an introvert or an extrovert?
Another great question to get him sharing a little more about himself! Knowing how to approach introverts vs extroverts is always a good thing, too!
So what are you up to this weekend?
Give him a chance to tell you what he has planned and the opportunity to invite you too. If you’re especially confident, ask him if he’s up for a plus one!
You smell great, what are you wearing?
What a lovely excuse to lean in a little closer and breathe in deep…
Have you ever been in love?
A flirty question like this will tell you both what his track record has been so far and what he is looking for in his next relationship; is he interested in a soulful, loving connection, or is he looking for something “just for fun?”
If I were to tell you you could ask me literally anything, what would you ask?
This gives him permission to get a little personal, doesn’t it???
How are you even single, you’re basically a dream guy!
Again, HINT HINT, buddy!
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 follow-up question: what’s your favorite way to be kissed?
What is the most romantic thing you’ve ever done for a girl?
This will show you what he considers romantic. You might also help future 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!
35 Flirty Questions to Ask Him – Boyfriend Level
These flirty questions are perfect to ask your boyfriend, just beware some of them get a little spicy!
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.
Have you ever been caught in the act?
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 dirtiest 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!
Do you like to be spontaneous when it comes to sex?
This is very helpful knowledge to have, indeed!
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 was your first impression of me?
This is a great thing to ask a guy when you’ve been together a while 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 if they are a little spicy!
What is your favorite song to get down and dirty to?
What songs do it for him?
What was the worst part of your last relationship?
This question always offers an interesting insight into a partner.
What does the ideal relationship look like to you?
This is a great question to ask your boyfriend to find out what he values most in a relationship.
Do you like dirty talk or more romance?
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.
When you think about the future, what do you see?
Does he see you in his future? Hopefully, this gives you a great shared future to look forward to!
What are you thinking of right now?
This one works best if you can ask while physically doing something a little flirtatious, like maybe biting your lip, twirling your hair, or even reaching out to caress his arm.
What outfit do I wear that you like the most?
Find out what you wear that drives him wild, then wear it a little more often!
Fast or slow?
Non-specific questions like this can be a fun way to find out where your man’s head is at!
If money, time, and obligation weren’t a barrier at all, where would you want to go right now?
Hopefully, his answer is going to involve whisking you off somewhere exciting!
What is the one thing you want to physically do with me that we haven’t done yet?
This one is pretty direct, make sure you’re prepared to hear the answer!
If our relationship were a song, what song would it be?
These kinds of questions are great to gauge the temperature of a relationship!
Do you like morning sex?
Again, direct! He will probably love it.
Is there anything about our relationship that scares you?
This is a vulnerable question, so make sure you and he are both in the right mental place to be a little vulnerable with each other here!
What is something that you thought would break you, but it only made you stronger?
Give him a chance to tell you about his personal growth!
What’s the coolest thing you’ve ever gotten away with?
Let him brag a little here!
In a Genie in a Bottle situation, what would your 3 wishes be?
Finding out your man’s 3 wishes might help you make those wishes come true!
If you could travel back in time to a different era, where would you go and why?
Would he like to be a knight in a medieval castle and have you as his princess? There might be some fun roleplay ideas that come up from this question!
What was your first time like?
Maybe this will get you two talking about your first time together, too!
If you were designing your dream girl, what would she look like?
K, if he doesn’t knock this one out of the park by describing you…!!!
Have I ever given you butterflies?
Another softball question for him, but sometimes it’s nice to make it a little easy for them!
If our relationship were a movie, what movie would it be?
Hopefully, it’s a sweet rom-com and not a tragedy!
If we had to rank our kisses… what would be your favorite?
It’s always fun to walk down memory lane a little bit, and the answer might just surprise you!
What do you remember most about our first date?
Another little stroll down memory lane to get you both remembering how far you’ve come!
If you had to tell the story of us with emojis only, what would it be?
This is a cute one when you are asking your man flirty text message questions!
25 Flirty and Dirty Questions to Ask Him – 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 fun answers!
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 limits. Where is 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 fun goal, but it is not for the faint of heart! Stay hydrated, friends.
Have you ever been handcuffed or blindfolded? Do you want to be?
It might be something your husband’s into. You 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 sexiest?
Finally, find out what makes him feel his best and most attractive. Perhaps you can recreate those conditions ASAP.
If we had our honeymoon over again, would you change anything?
See if there’s anything your hubby wishes he did or didn’t do on your honeymoon!
Would you ever want to go to a nude beach together?
Maybe don’t ask this one if you have no interest in it yourself, would hate to open up this Pandora’s Box if it doesn’t appeal to you at all!
What is your favorite sex scene you’ve ever seen in a movie?
When he answers, ask if he wants to watch it together and maybe act it out later!
What is your favorite memory of our wedding day?
It might surprise you to know his favorite memory of your wedding day!
If you could design the perfect lingerie for me, what would it look like?
Encourage him to get as detailed as he can, then make his dreams a reality by searching for the closest item possible!
What do I taste like to you?
Veeeeery steamy question, this one!
If we were building our dream home right now, what would it look like?
It’s never a bad thing to keep dreaming together!
Would you ever want to go skinny dipping together?
Another one you’ll want to only ask if you’re willing to take that leap yourself!
Is there ever anything I do that you brag to your friends about?
It might be interesting to hear what your man brags on you about!
Is there a fantasy that you have that you haven’t ever told me about?
Sometimes even your spouse will surprise you with what they haven’t shared yet!
Out of all of the places we’ve been intimate, where was your favorite?
When he answers, you might start planning your next date night to recreate his favorite!
There are tons of cute and clever ways to show love and affection! Even if you’ve been married 30+ years, flirting is always a cute way to say I love you. Have fun asking your man these flirty questions!
Want more? Check out these relationship posts next:
- 10 Relationship Red Flags To Watch Out For, According to Therapists
- 8 Real Relationship Goals All Couples Should Have
- 10 Signs He Loves You + How to Deal if He Doesn’t
- 110 Flirty Texts for Him: Fun, Cute Text Messages He’ll Love
- 95 Flirty Texts for Her: Sweet Messages to Make Her Swoon
- 50 Christmas Pick Up Lines and Flirty Texts
Amy Hartle is the co-founder and owner of Two Drifters, where she blogs about romantic and couples travel, relationships, honeymoons, and more. With a Master’s in English and a BA in Musical Theatre, Amy loves to write quality content as well as to entertain, and she hopes to do a bit of both here on the blog! Amy is happily married to her husband Nathan, and when not working on their sites, Amy & Nathan can be found cuddling, reading, and enjoying delicious lattes.