Flirty Questions To Ask a Guy

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So you’re looking for flirty questions to ask a guy? Maybe it’s flirty questions to ask on dating apps? Flirty questions to ask your crush? Or perhaps even flirty questions to ask your boyfriend? 

Flirty Questions To Ask a Guy

To make it nice and easy, we’ve broken our down our flirty questions into three key categories (although there’s likely to be some overlaps so be sure to have a scan through them all!)

We’re looking at:

  • First up: Flirty Questions To Ask On Dating Apps
  • Then we’ll look at: Flirty Questions To Ask Your Crush
  • Finally there will be: Flirty Questions To Ask Your Boyfriend

This means that no matter what your situation – you’re well equipped with flirty questions to take conversation in the direction you want it to go!

Uh huh… that’s right, these men aren’t going to know what’s hit them! 

Flirty Questions To Ask On Dating Apps

So let’s start it off with some flirty questions to ask on dating apps. This is before you’ve met the guy.

Perhaps you want to get to know him, maybe you just want to test the waters.

You also want to to see if there seems to be a bit of a romantic spark there, and try to install the right dynamics right from the start.

So some of these questions will be perfect for that!

Flirty Questions To Ask a Guy – Based On Complements

So the first set of questions to ask a guy on dating apps integrate subtle little complements. Using these is a great way to subtly flirt with a guy, whilst making them feel good.

  • Your smile is amazing! Did you ever have braces or are you just dentally gifted? 😉 
  • Wow. Your body looks unreal! How often do you work out? 
  • Umm, how are you still single? I’m going to assume single by choice because it’s the only explanation that makes sense to me!
  • Your family must have great genes. I mean, how did you get so handsome?! 
  • So, aside from taking my breath away (ha!), what do you do for a living?
  • Well you seem to tick a lot of boxes. What’s the catch, hey?
  • Ah, you are such a funny guy! Is this where your pulling-power lies? 😉
  • Your smile is amazing! I bet that melts a few hearts, hey?
  • You look like you could be an absolute heartbreaker! But I’m hoping, if so, you’re reformed! Where you at right now? I’m so not being your next victim!
  • Damn. You are DREAMY! How long have you been single?

On this note, you may also like to have a read of this post for how to start a conversation on a dating apps. It ties in some good flirty questions to ask a guy, but means the chat gets off to the best start… and you also get more responses! Uh huh, you can thank me later!

Flirty Questions To Ask A Guy To Get To Know Him

These questions have a flirty little undertone, whilst still providing pretty interesting conversation. It certainly beats the small talk anyway!

  • Okay so what do you prefer – cuddles or kisses? If you could only pick one for the rest of your life?
  • Another big question – big spoon or little spoon, which do you prefer? Be honest! There’s no shame in preferring to be little spoon ever now and then 😉
  • What do you think is the best thing about dating?
  • And what do you miss most about being in a relationship?
  • What do you find most attractive in a woman? We can say physically if you like 😉
    Then go on to ask them what they find most attractive personality wise too.
  • What wins you over more… brains or beauty?!
  • What do you think is your best physical feature?
  • [If you’re feeling brave and it doesn’t come across as pushing for complements…] What do you think is my best feature?
  • Are you a romantic kind of guy?
  • What’s the most romantic gesture you’ve ever done?
    When he answers: Ooh, the stakes are high now then! I know what kind of thing to expect 😉

Let’s Keep Them Coming…

  • What are you like in a relationship?
  • Are you affectionate? Do you miss that intimacy?
  • What do your weekends look like? And how would I fit into them? 😉
  • Do you prefer staying in or going out?
  • What are your most frequently used emojis? This will say a lot about you 😉
  • Are you ticklish?
  • What gets you all flustered?
  • Do you get embarrassed easily? Or no shame? 😛
  • What’s one thing that not many people know about you…?

The No1 Question To Ask a Guy On Dating Apps

Then of course, if you’re looking for flirty questions to ask a guy on a dating app and the conversations going well, you could just come out and say it –

So when are we going to grab a drink? 😉

Uhhuh, be bold, be brave! Go for what you want. You’ll actually find he loves it! It will – most likely – make a refreshing change!

Flirty Questions To Ask On Dating Apps

Flirty Questions To Ask a Guy On a First Date

So I thought it would also be pretty handy to throw in some flirty questions to ask a guy on a first date.

You’ve just met him, you’re having a good time, you feel a little chemistry and you want to build on that. What do you do? You try a few of these lines!

Note: there’s a fine line between coming across as desperate and “easy”, and simply using your own power of seduction with these flirty question ideas. But go with what flows! Also never force it… Only try these out when you’re getting the interest back!

  • So what do you think about a girl making the first move? [Lean in to tease him.]
  • Do you like a confident woman? Or is it a little intimidating for you? [Say it with a wink!]
  • What are you thinking, right this very moment? [Timing is key with this one. Pick your moment!]
  • How was the experience of your very first kiss? [Little blast back to the past!]
  • Do you think the whole “when you know, you know” is true in love and relationships?
  • What’s the chestiest pickup line you’ve ever heard or used? [Keep it fun and lighthearted!]
  • So if you were to chat me up at random, what would you first say to me? [Play it out!]
  • So if I was going to approach you, how well would this line go down? [Again, try one and play it out! Show that you’re up for a laugh!]
  • What do you think is the most important thing in a relationship? [A great question to ask after you’ve been laughing!]
  • Do you think emotional intimacy is just as important as physical intimacy? [This one digs a little deeper but interesting chat is important on a first date, and you can still be a little flirty with it!]

BONUS: Want to add a bit more humour into the conversation? Here’s 30 Flirty Jokes For Your Date: Click here to read.

Flirty Questions To Ask Your Crush

Next up we have flirty questions to ask your crush.

Your crush could be someone you’ve started dating, someone you’ve always had a soft-spot for, or maybe even someone you just want to date!

Depending on your situation, some will be more suitable than others. You may also like to go back a step and try some of the flirty questions from above. 

Remember – this list is just for a bit of inspiration! Once you get into it, more are likely to flow, just like they will as your confidence grows. So have fun with it!

Flirty Questions To Ask Your Crush After a Date

  • What was the first thing you noticed about me?
  • Did you feel a little bit of chemistry there too? 😉
  • Based on first impressions – how would you describe me in three words? Don’t hold back 😉
  • Be honest – have I made it into any of your dreams yet? 
  • Or did I make it into your dreams even before we met? What happened?!
  • If you were to dream about me, what little fantasy would you have playing out there?
  • Do you think you could handle me then? I’m not too much for you? 😉
  • So what are we doing on our next date then?

Recommended Read: How To Tell if a Guy is Flirting With You

Flirty Questions To Ask Your Crush

Flirty Questions To Ask Your Crush 

  • What physical feature do you find most attractive on a woman?
  • What do you find completely and utterly sexy?
  • So what do you think is your best physical feature then? I know which I think is!
  • If you were going to try to seduce a woman… what would you do?
  • Are you confident about your… seduction abilities? 😉 Let’s put it to the test!
  • Have you ever skinny dipped before? And would you ever do it? With me, maybe?
  • What’s the most “out there” thing you have ever done? Wow me with your boldness! 😛
  • What’s your idea of the perfect date? And no, I’m not trying to get inspiration here!
  • What do you think makes a relationship great?
  • What do you miss most about being in a relationship?

Let’s Keep Them Coming…

  • What puts you in a great mood?
  • What’s better – naughty or nice?
  • Shower alone or shower together – which would you say?
  • What would you say you’re more of – a giver or a taker?
  • Do you like massages? Are you any good at giving them?
  • What sort of pressure are we talking when it comes to these massages? (Not that I’m making plans or anything! :P)
  • Do you like surprises? And are you big on them?
  • What’s something about you that would probably surprise me?
  • Do you have any habits that could drive someone CRAZY?!
  • What’s one of your guilty pleasures? (No judgements here!)
  • What’s one question you’re dying to ask me? Come on, I know there must be something there! 😉

Flirty Questions To Ask Your Boyfriend

When it comes to flirty questions to ask your boyfriend, you can definitely be a little bolder! But a few ideas to get the inspiration flowing…

  • What’s your favourite body part of mine?
  • Do I ever still make you nervous? How about when I do…this? [Creativity required]
  • What turns you on the most?
  • Where do you most like to be kissed?
  • Where’s your favourite place to kiss me?
  • Do you have an ultimate fantasy? Perhaps one I don’t know about?
  • What’s the most… exciting… dream you’ve ever had about me?
  • If we could spice up our relationship in one way (and any way!) what would you like us to do?
  • What’s your favourite memory of us? How about our wildest one?!
  • If you could recreate a scene from a movie with me, which one would it be? Sell me it well, and you may be in luck! 😛

Combine these flirty questions to ask your boyfriend with looks, a little touch. You can make almost anything sound a little bit flirty if you say it in the right way. So have a go! Have fun with it!

For more tips on how to spice up your relationship, click here.

So There We Have It…

You are now equipped with heaps of flirty questions to ask a guy – no matter what stage of the relationship you’re in.

Like I said, scan through them all, have a read, as many can be adapted to make suitable for the guy you want to up your flirting game with.

Hope this helps!


Flirty Questions To Ask a Guy

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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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