100 Flirty Questions To Ask A Guy (And Be Irresistible)

Welcome to The Dating Dairy’s top 100 flirty questions to ask a guy! The best way to go about this is to divide a hundred questions into relevant sections – you can ask these questions depending on your comfort level with a particular man.

If you want to keep it naughty and light, then you have to check out the section featuring questions that are dirty and flirty. Similarly, if it’s a situationship and you are perhaps ready for the next stage, then you can take a cue from the section featuring multiple romantic questions.

So without wasting any more time, let’s get started with the top hundred flirty questions to ask a guy!

Hot As Hell: Dirty Questions To Ask A Guy

There’s LITERALLY no end to all the many sexy questions you can ask your crush. Think about it – if you try, you will probably end up adding a dirty twist to even basic questions like what’s your ice cream flavor? It’s hot as hell when you are expressive about your sexual needs – you know you can be irresistible to your crush with the right questions.

Here are the top dirty questions to ask your crush!

Do you like women who ALWAYS prefer making the first move?
Am I making you nervous right now?
Am I inside your head when we are not spending time together?
What’s your favorite spot for making out?
Do you think you are aware of what a woman needs sexually?
Are you shy inside the bedroom?
What are you wearing right now?
Have you ever checked my body out?
If you could ‘do’ one celebrity, then who would that be?
What’s the first thing about me that caught your eye (if you know what I mean)?
Would you like it if I wore hot lingerie for you? Or would you prefer me naked?
What do you prefer – pantyhose or stockings with a sexy garter belt?
Have we done anything dirty in your dreams yet?
Do you like it when I lightly bite my lips?
How long do you like foreplay to last?
Would you enjoy watching porn with your partner…or me, for that matter?
Do you like it when I touch you?
What’s the sexiest thing about me?
Did you ever have sex with more than one person in a single day?
Do you want me to take this shirt off, or would you like to have the honors?
Do you have a fetish or a sexual fantasy?
Do you like spicing up things in the bedroom?
Would you ever accept a gift or money for sex?
Have you ever been in a threesome?
When it comes to intimacy, what turns you on the most?
When was the last time you sexted?
What do you like in the bedroom – taking charge or the backseat?
What is your biggest kink?
What do you prefer – lights off or lights on?
Which part of your body can I touch right now and turn you on?
What do you like more – sexting or dirty talking?
If I stayed with you for 24 hours, what would you do to me?
What is the most romantic thing that you have done?
What would you ask from me if you knew that my answer would be ‘yes?’
If I ask you, would you dare to send me your nudes?

Love Is In The Air: Romantic Questions To Ask A Guy

Of course, if you are looking for the best romantic questions to ask a guy, then that means things are definitely starting to get serious with a mystery man. I mean, it’s 2023, and situationships are ruling the day. But does that mean – true love has ceased to exist? Not really! Ladies, you cannot let true love disappear – if you are ready for the next step, then you go, girl!

Here are some of the best romantic and deep flirty questions to ask a guy!

Have you ever been in a serious relationship before?
Who was the first person you fell for hard?
What is your love language?
Do you believe in love bombing?
Have you ever handled a major heartbreak?
Do you easily fall in love?
Do you prefer taking time and going slow or moving quickly in a relationship?
When do I see you next?
Is it fine that I kind of want to lean in and kiss you right now?
What is your biggest turn-on?
Do you believe in soul mates?
How old were you when you had your first kiss?

What’s the most humiliating thing you have ever done to get your crush to notice you?
What are your relationship dealbreakers?
How to deal with conflicts in relationships?
Have you ever cheated on your partner?
Are you monogamous?
What does your dream date look like?

Has any of your former partners cheated on you?
Do you consider yourself a good kisser, for starters?
Do you think that everyone person has one soul mate?
What do you prefer: an emotional connection or a physical relationship?
Do you believe in astrology?
Do you think that men and women can be ‘just friends?’
Is there anything that you wish you could change about me?

Did you ever develop feelings for fictional characters?
What’s your favorite love song?
What was your first kiss like?

Do you think of yourself as a red flag?
Do you like getting breakfast in bed?
What do you like about me the most?
How do you prefer expressing your feelings, especially in a romantic relationship?
Do I make you feel special?
See Also

Dating 101

32 Dirty Texts To Make Him Blush
Have you ever dreamt about me?
How would you want your partner to express their love for you?

It’s Just Another Flirtationship: Flirty Questions To Ask A Guy

There are so many freaky questions to ask your crush – but not all of them will get you what you want. So, what flirty questions to ask a guy you like – questions that your crush will relate to and, most importantly, will react to? What’s the point, really, if your flirting efforts fall flat and miss the target?

For all of you stuck in a flirtationship, here are some of the best flirty questions to ask your crush.

Do you like it when I flirt with you?
What’s your type – soft and feminine or dominating and assertive?
What is that one temptation that you can never resist?
What do you prefer to be in bed – the big spoon or the little spoon?
What’s one film title that can accurately describe your kissing style?
Besides talking to me, what was the highlight of your day?
Would you date someone who is absolutely hot or someone who’s just smart?
What are your thoughts on ghosting?
What’s one hot thing that you have done in a public space?
Have you used any sex toys?
How many people are you flirting with at the moment?
What is your guilty pleasure?
What is your favorite way to flirt with a woman?
What is the nicest thing that someone can actually do for you?
What makes you feel comfortable with someone you have been crushing over?
What does your ideal date night look like?
Have you ever dated any friend of yours secretly?
What’s the worst pick-up line you have ever used?
What do you like more – nice or naughty?
What is the most romantic thing that someone has ACTUALLY done for you?
What is your favorite memory about me?
Do you believe in love at first sight?
What’s your favorite pick-up line, one that always works?
Would you like to go out on a movie date tonight?
Would you like to go out for dinner later this week?
What was your first impression of me?
Do I make you feel safe?
What color looks the best on me?
What’s that one song you like associating with me?
What couple activity would you like to try with me – couples yoga or something else?

The Art Of Flirting – What A Rewarding Experience!

Flirting is a rewarding experience – it’s so healthy! It all depends on whether or not you find the experience exciting. If flirting excites you, then you can indulge in the same, but it is also possible that you have never really engaged in healthy flirting. As a result, you are mostly left confused about how to go about it.

But it’s so simple – just find the right flirty questions to ask a guy and, more importantly, at the right time. Tell us what your thoughts on these questions are. And while sharing your thoughts, don’t forget to share your flirty experiences with us in the comments below.