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40 Charmingly Flirty Questions to Ask a Guy

Do you wish that you could be a little more flirty and fun when chatting with your new guy? Maybe have some flirty questions you can use to keep the conversation exciting? I get it, you want to level-up your flirting game to keep him interested.

If I’ve hit the nail on the head, here are 40 flirty questions you can ask this guy to hold his attention.

Table of Contents

40 Flirty Questions to Ask a Guy

Disclaimer: These questions are always better when asked with a flick of the hair or a flutter of the eyelashes.

Related: 20 Must-Know Online Dating Questions to Ask Before Meeting

#40 – What Did You Think When You First Saw Me?

If you’ve only recently crossed paths with the dude in question, this conversation-starter is a good way to find out what he initially thought about you.

Like, did he fancy you at first sight or not? Not to worry — all should be revealed.

Related: How To Flirt With Men10 Ways To Keep The Chemistry

#39 – What Do You Look for in a Woman?

By asking him this flirty question, the idea is to determine what type of woman he wants for his next big relationship.

And if his answer aligns with the type of woman you are? Happy days!

Related: Does He Want A Relationship or A Fling?

#38 – Which Qualities in a Woman Do You Find the Most Attractive?

Upon first impression, you’d be forgiven for thinking this question is pretty much the same as the previous one.

However, he may have answered “someone I can trust” for #39. This question makes him highlight what’s most important to him — and it can say a lot about him, as a result.

For example, if he answers “a big butt,” there’s a good chance that he might be shallow.

Remember, you are a high-value woman and you always have to keep up this attitude. Asking him flirty questions like this reveals if he’s on your level or not.

Related: What Makes A Good Husband? – 10 Traits of A High-Quality Man

#37 – What Are Your Most Attractive Qualities?

This question allows him to put his best foot forward so-to-speak. It gives him the opportunity to communicate his strengths in his own words.

And if he’s selling himself hard, you know he’s into you.

Related: How To Know If A Guy Likes You

#36 – Am I Your Usual Type?

If he says “no” to this question, don’t worry.

According to Daily Mail, it’s a good thing if you’re not his usual type.

How come?

  • Love doesn’t stick to lists. You connect with someone based on the person they are. If you have other qualities that are so powerfully attractive to your guy, it will make him override his typical “wish list.”
  • Just because he has a type, doesn’t mean he won’t find other women attractive. Looking appealing to him at the start matters, but you need to have so much more to offer if you want to keep him interested long-term.
  • It means he’s serious about finding love. FYI, it’s a sign of immaturity if he automatically dismisses you for “not being his usual type.”
  • It hasn’t worked out for him so far with his “usual type.” (And there’s often a reason for this.) It’s time for him to break the mold (with you). 


Related: How To Tell If He’s Attracted To You

#35 – What’s My Best Feature?

With this flirty question to ask a guy, you’re essentially trying to discover what he likes the most about you (physically) without asking in those exact words.

Whether he answers honestly or not, this should be a massive ego-booster.

#34 – What Do You Think Your Best Feature Is?

Similarly, this question gets him to communicate what he likes the most about himself physically.

And if you disagree with the feature he chooses, don’t be afraid to tell him to boost his ego.

#33 – What’s Your Favorite Thing About Yourself?

Now that you’ve covered his best feature, you also have to cover what he believes is his best personality trait.

Again, if he answers something different to what you would answer, tell him. The opposite sex is partial to a bit of flattery. 

(In fact, aren’t we all?)

Related: Lust Vs. Love – Will the Passion Last?

#32 – What’s Your Favorite Thing About Me?

This question is great for making you feel all gooey inside. 

After all, it opens up the floor for a sweet and romantic answer, i.e. “how kind you are” or “I love the way you make me feel like I can be myself.”

All together now: aww.

#31 – What’s Your Idea of a Perfect Date?

If you’ve not yet been asked out by this guy, this is a great question to help things along.

Why? Well, it gets him thinking about taking you on a date.

#30 – What’s Your Biggest Turn Off?

By getting him to answer this question, you’re practically asking “what shouldn’t I do to turn you off?”.

And then make sure you don’t do whatever he says to keep yourself in the picture!

Related: How To Make A Man Fall In Love With You

#29 – What’s Your Biggest Turn On?

By asking questions that are sexual in nature, you can take the flirting up a notch.

Make a note of the answer to this question because you may need to refer to it at a later date. Wahey.

#28 – Are You Ticklish?

Sure, this may seem like a bit of a weird question.

However, if you follow it up with trying to tickle him as a way of touching him, it makes a lot more sense. Right?

#27 – Have You Been Working Out?

Likewise, this question is more effective when you ask it while referring to his biceps and touching his arm.

If you’re lucky, you might just make him blush.

This is a really flirty thing to say and saying it will surely make the sparks fly!

Related: How To Text A Man – The Rules of Texting In Today’s Modern Dating

#26 – What’s Your Favorite Sexual Position?

According to Women’s Health Mag, his favorite sex position says about him:

  • Missionary — he either likes to be in control, he’s a little insecure and needs reassurance from his lover’s response, or he’s not particularly adventurous
  • Doggy – this taps into his territorial animalistic instinct as king of the jungle and suggests he may fear intimacy and be unromantic
  • Woman on top – he’s confident in being dominant but he’s also fine with being submissive because he just wants to make you happy
  • Spooning – he’s passionate, eager to please, and romantic
  • Standing – he’s mischievous, adventurous, and wants to have as much fun as possible

Regardless, it’s interesting to learn whether his answer matches yours.

#25 – Where’s Your Favorite Place to Have Sex?

Guess what you do by asking him this cheeky question?

You get your guy thinking about having sex (and, more specifically, having sex with you) in his favorite place. Hello, desire.

Related: Why Do Men Pull Away After Sex?

#24 – Where’s the Craziest Place You’ve Had Sex?

This question will help you determine how sexually adventurous he is.

It can also indicate whether your bedroom personalities will click or clash. (Fingers crossed it’s the former!)

#23 – Do You Like to Be the Big Spoon or Little Spoon?

If you like to be the little spoon and he answers “big spoon,” this is a great foreshadowing of things to come.

That said, if he answers “little spoon,” you may have a future challenge on your hands.

Related: 5 Dating Standards that Actually Matter

#22 – What’s Your Idea of a Perfect Kiss?

If you’re on a date with your crush and you want him to kiss you, the best thing to do is talk to him about kissing.

(And hopefully, he’ll get the hint!)

#21 – Where’s Your Favorite Place to Be Kissed?

Again, if you’re on a date with your crush and you want to go beyond just making out, talk to him about going beyond making out.

It’s a simple formula, but it really does work.

Related: How Many Dates Before You Have Sex?

#20 – What’s the Most Romantic Thing You’ve Ever Done for Someone?

On the other hand, if you want to prioritize building a connection with him that could turn into your next big relationship, you might want to keep the conversation PG-13.

Instead of bedroom-related questions, you could ask him about his past relationships and romantic endeavors.

#19 – What’s the Most Romantic Thing Someone Has Ever Done for You?

Want to know how you can tell this dude you like him without saying the actual words? Use your actions.

Take note of his answer to this question so you can make an even bigger (and better) romantic gesture in the days to come.

#18 – Do You Think Guys Should Always Make the First Move?

This question is interesting if you’re at the very beginning stages of dating someone.

Regardless of whether he says “yes” or “no”, ask him why so you can determine if you’re on the same page.

Related: Should I Call Him? – The Easiest Way To Know

#17 – Do You Take the Lead in a Relationship?

In addition to #18, his answer to this question may also reflect his expectations in a relationship.

If you want him to say “yes,” you’re not alone.

According to Psychology Today, you might seek a dominant partner for the following reasons:

  • You experience anxiety and are looking for security
  • You’re not a natural leader
  • You get bored easily and want a more thrilling relationship

However, you might want to be the dominant partner if:

  • You’re a natural leader
  • You like to explore new experiences
  • You have a tendency to nurture and protect people

Either way, if you want things to progress with this guy, you need to work out whether you’re ultimately going to be a good match.

#16 – How Are You Still Single?

This flirty question to ask a guy is quite forward and suggests that you want to be the one to take the guy off the market.

Therefore, proceed with caution if you met him, like, 30 minutes ago.

Related: How To Make A Man Chase You

#15 – What Are You Like as a Boyfriend?

If you’re seriously thinking about this dude becoming your boyfriend one day, you need to know if he’s going to be a good one.

Keep in mind that he may not give you an honest answer if he knows he’s got a shady relationship history.

Related: 20 Questions To Ask A Guy Before Meeting Online

#14 – What Do You Expect from a Girlfriend?

Pay attention and listen. Do his relationship expectations align with yours?

If not, it’s kinder to yourself (and him) to nip it in the bud now.

#13 – How Many Times Have You Been in Love?

If your guy is 25+ and he’s never been in love, I’d see this as a big red flag.

How come? Well, it conveys emotional unavailability — and you can never build a healthy and happy relationship with someone who’s emotionally unavailable.

Related: How To Deal With Emotionally Unavailable Men

#12 – What Makes You Fall in Love With Someone?

Full disclosure: These questions about love should be saved for someone who you’ve been dating a little while.

If you try and ask your crush this (who you’ve met once), you might scare him off.

Related: The 5 Love Languages Explained

#11 – How Quickly Do You Fall in Love?

See #12.

#10 – What Are Your Favorite Pet Names?

This is a good question to bring up when you’re talking about past relationships (which is probably at least third date territory).

It can be an effective way to lighten the mood after a particularly deep conversation.

#9 – If You Could Spend an Entire Day With Me, What Would We Do?

How he answers this one is a good indicator of how he feels about you.

If he says that he wants to take you on an exciting trip that ends with dinner and fireworks, he likes you romantically.

On the other hand, if he tells you he’d take you to the local sports game so you could hang out with him and his buddies? I’m sorry to tell you that he might see you more as a friend.

Related: Signs He’s Falling For You Hard

#8 – What Excites You?

This question is ideal for learning more about what he’s passionate about, such as hobbies, work, or other interests.

It allows him to open up a bit more and get him talking.

#7 – What Makes You Flustered Easily?

If he reveals his most embarrassing secrets when he answers this question, he trusts you. 

Alternatively, if he keeps things light or makes a joke, he’s not ready to let his emotional guard down.

#6 – Do You Have a Celebrity Crush?

His answer to this question tells you who he considers his “dream girl.”

But if you’re nothing like her, don’t sweat it. See #36.

#5 – When’s the Last Time You Felt Butterflies?

By getting him to open up and talk about his feelings, you’re getting him to deepen his emotional relationship with you.

After all, you don’t discuss your feelings with just anybody. Right?

#4 – What’s Your Favorite Pick-Up Line?

If you try to ask him #5 and he just freezes, this is a sign that he’s not ready to emotionally advance the relationship.

Instead, switch up the conversation and lighten the mood by asking him this belter.

#3 – What’s the Worst Pick-Up Line You’ve Ever Used?

See #4. Cue the hilarious responses that get you both laughing and having fun.

(One of my personal favorites is: “If you were a Transformer… you’d be Optimus Fine.” Face-palm.)

#2 – What Would You Do if I Kissed You?

This is something you’d ask your date right before you were planning to lean in and kiss him.

If you’re confident he’d kiss you back based on the vibe he’s giving you, you don’t need to ask this. (Just go for it.)

If you’re not, ask away.

Related: How To Make A Man Fall In Love

#1 – When Are We Going on Our Next Date?

Obviously, replace “next” with “first” if you haven’t been on a date with your crush yet.

Again, to save yourself from humiliation or rejection, you need to go off the reactions he’s had to the other flirty questions you’ve asked him.

If he’s been cold and standoffish overall, he might not be into you and you’re better off parting ways.

How To Attract High-Quality Men

I hope you found this article helpful, but it does you no good if you’re not attracting High-Quality.

If you’re a confident and successful woman, you need a confident and successful man.

If you’re interested in learning what High-Quality men look for in a woman, check out my Free Guide on “How To Attract Higher-Quality Men” by Attracting Better Men.


Asking flirty questions is a great way to find out more about the guy you like, but only if you have the time to give each other your undivided attention.

You should also avoid bombarding him. Sell it as a “get to know each other” game so you can get in as many as possible.

Then see how he responds. Is he enthusiastic? Is he excited to ask you questions too? You can usually tell when someone is enjoying themselves.

And if this is the case for you guys, it could be the start of something amazing!

Love, your favorite dating coach.


Lana Otoya

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