Any relationship or friendship, regardless of the type, is bound to get boring at some point. Thanks to question games, you have everything in your power to revive the feisty interesting conversations.

Building something intimate with someone calls for sheer soul intelligence, something that can be greatly facilitated by flirty questions. Not only would you gain the direction to talk about things constructively, but also correct some of the assumptions and misconceptions you have about the other person.

With our perfectly- compiled examples and their descriptions, we hope to enhance your intimate connection with your crush or better half. Here’s your chance to dig deep into each other’s thoughts and feelings. Ladies, it is worth noting that men are naturally receptive to such topics, so you’ll have the easiest time sparking this conversation.

You could choose to approach it as a “would you rather” question game or in the form of “who is most likely to questions“. As long as you maintain the flirty nature and ideology. But first, take a look at our comprehensive list

Make the most out of it!

Best Flirty Questions to Ask a Guy

#1: Why do you always keep making me smile?

One of the best questions to start a flirty game. You’ll get him blushing from the very beginning. Don’t expect a definite answer though.

#2: Which do you prefer between making out and cuddling?

Most guys like jumping right into the action. But who knows, people are different.

#3: What is the one thing people would never guess about you just from looking at you?

Knowing something about them that most people don’t, gives you an upper hand in more ways than you’d imagine.

#4: Tell me some of the things that bring a smile to your face, regardless of the time or situation?

Throw in one of those things in the game to keep him smiling. Whether a song or a funny clip.

#5: Do you have any preference when it comes to nicknames during intimacy?

This will help set the mood for deeper flirty questions. In case you get to the next stage, you’ll know what to call him in bed.

#6: How is someone amazing like you still single?

One of the most common tricks to know whether he is taken or not. Don’t get your hopes up, especially if he is super cute.

#7: What is the hardest thing you have ever done in your life?

You could use such questions to throw him off and at least learn something meaningful about his life. Make it better by telling your hard experiences as well.

#8: What would you say is your best and worst feature in girls?

Cross your fingers and hope to God that you don’t get featured in the latter section

#9: Would you try describing me in five simple words?

Ideally, this should appear in the hard section, especially for first-timer dates. But it doesn’t hurt trying to hear someone’s first-time opinion/perception.

#10: What comes to mind when you hear the word ‘foreplay?’

Here’s to turning things a notch higher and exploring higher grounds. Share what you like about foreplay and get that talk going!

#11: What’s the one thing you are proud of about yourself?

Well, every once in a while, everyone wants to share some of their great achievements. He could be more modest than you think though.

#12: So tell me how you got to become so cute and adorable?

Don’t be amazed if he turns this into a one-liner about you. If the bond is mutual, you might hit it off sooner than predicted.

#13: Describe your perception of the perfect girl?

The sole reason for this is to compare yourself to his idea of the perfect girl. Don’t ask if you’re not ready to get disappointed.

#14: What is the one thing you enjoy sleeping in?

The open-ended nature of this question makes it worth asking. Go ahead and speculate how you would both be in bed.

#15: If you were to see women in one lingerie all your life, what would it be? And in what color?

Time to know whether he has a rich preference. Either way, he must have seen quite the number of lingerie to come up with the ideal option

#16: What is the shortest and longest relationship you’ve been in? Why did they end?

Story telling at its finest. Tell some of your relationship experiences to be at par. Then distract yourself with more flirty questions

#17: Is there something about me you can’t stop thinking about?

If you are in the early stages of talking and flirting, this might come in handy. Keep that conversation fueled and mention some of the things you fantasize about.

#18: On a scale of 1-10, how do you like when I engage you in some dirty talk?

As expected, most guys would go for an 11/10, unless he has friendlier intentions for you.

#19: What is the one outfit you’ve been dying to see me in?

Figuring out what a guy fancies in terms of dressing could be hard. But this question does the job

#20: Randomly mention any of your turn-ons and turn-offs?

This should be the first question during the first stages of any relationship. Think of it as a precaution.

Hard Flirty Questions to Ask a Guy

#1: Assuming I could transform into your genie for a day, what three wishes would you make?

You could easily understand a man’s motivation and intentions from his three hypothetical wishes. If he makes all of them about you, he’s probably lying.

#2: What intimate thing relaxes you when you are stressed out?

How about you give him his intimate fantasy after the game? Depending on how he participates

#3: What are some of the things you’ve purposed to try before you die?

You might expound the question further or leave it general just to see where the ride goes.

#4: Do you ever watch romantic movies? If so, which kind?

If you fancy hopeless romantics, you better hope he meets your expectations.

#5: If you could watch one romantic movie with me for the rest of the year, which one would it be and why?

If the previous question was a no, you can always shift the question to another genre or skip to the next ones. It only gets better.

#6: Are there experiences you’ve had with girls that have changed your life? If so, do you mind sharing?

Any guy, however good or bad looking, has had experiences with girls. Time to find out how life-changing these experiences can be.

#7: Tell me something, whether big or small, that you have never told any other human.

You have to seem trustworthy for anyone to disclose their secrets to you. Unless you have both known each other for some time.

#8: What would you like your future family to be like and why?

Everyone has thought about this at some point. But it always seems hard settling on the ideal family goals. Compare notes and see if you could be compatible.

#9: How would you describe the perfect relationship? And what’s the closest to the perfect relationship you have been in?

Perfection is relative in every aspect. You might just have found the one who matches all your heart’s desires, or the extreme opposite. It’s wise to ask this.

#10: What is the hardest thing you have been trying to stop or overcome?

Unseen and unknown battles are often the hardest. Connect more with these deep hard questions.

#11: If you were to be given $10 million to make me fall for you, how would you do it?

What’s the fun of a flirty game without some creativity bit. You might want to give him some time for this one. Which puns and lines would get you falling for him?

#12: Where would you like to be kissed for as long as you lived?

Pray you’ll get an opportunity to use this on him someday. This part would be more fun if it went both ways. Spill some of your favorite spots as well.

#13: What is your idea of the best and most romantic date?

For someone you have known for a while, you might want to ask this just before his birthday. Life’s too short to not take your guy friends out.

#14: Are you ever intimidated by girls making the first move?

It’s always safe to be sure before making the first move. At a time where toxic masculinity is at its peak, you can never be too sure about someone.

#15: How would you react if a girl kissed you out of the blues?

Giving in to a random kiss doesn’t necessarily display disparity, but at the same time, no one should be open to everything that comes their way.

#16: Do you ever have dreams about me? If not, what’s the most sexual dream you’ve had?

Outrightly tells the guy that you want to get some dirty talk going. If he doesn’t dig this, then he’s probably not in the mood or is simply not interested.

#17: According to you, where’s the most appealing part to have a girl put a tattoo?

It would be wise to air this out to a guy who feels like a potential boyfriend. At the same time, you have to do whatever makes you happy.

#18: Would you rather have a girl who is always smart or always happy?

This cuts the hard category. Which is more vital? A happy face or a decisive mind?

#19: What are you looking for or idolizing in a girl right now?

We couldn’t end this section without giving you the chance to find out whether you are his dream girl. Keep an open mind though.

#20: How would you react if I put my hands under your shirt right now?

Quite the teaser! If you don’t get a blush from this one, you probably won’t get it ever.

Fun Flirty Questions to Ask a Guy

#1: Would you consider yourself an introvert or an extrovert when it comes to beautiful girls?

From the answer, you can easily tell whether he thinks of you as beautiful or not. Either way, don’t take things too personally.

#2: What is your idea of a perfect first date?

Throw in some ideas and scenarios to jog up both your minds and keep things interesting. Hint some of your preferences as well.

#3: For how long, have you been working out?

Don’t go posing this question to fat guys to gas them up. Ensure he has some gains first. Then watch a whole grown man blush.

#4: Assuming we were on a date, how do you think it would end?

With a kiss? With more than a few kisses? By all means, explore all outcomes. You might be in luck to find the perfect ending.

#5: What emoji do you use most when flirting?

Get him to describe it using gestures and laugh over it. To make it even more fun, take out your phone and text him the same.

#6: Is there anything you are currently obsessed with and why?

Talking about obsessions can be a little tricky especially if you aren’t well acquainted. But after the series of questions above, you’d have formed a great bond to ask this.

#7: What is your way of telling if someone is amazing or not?

There’s no straightforward answer to this. Watch and learn though, you are most likely to get all his peeves here.

#8: What is the most daring or sensual game you have ever played?

Looks might be deceiving. Ask and get to know some of the kinky activities you stand to try with him.

#9: If you had one chance to ask the prettiest girl in the world out, how would you do it?

Make him try it on you, and act as the most beautiful girl in the world. A few turndowns would be the perfect motivation for this one.

#10: As far as intimacy is concerned, what is the farthest you’ve gone on a first date?

If you still haven’t gone out on a first date, you would determine what to expect from this question.

#11: Do you have a lover or a girlfriend?

This should be the basic question for anyone you are interested in. Asking it while you are too deep in the game is still allowed though. It might offer some insights.

#12: Describe your best and worst kiss and what your idea of the perfect kiss is?

You’d be sure to get some interesting experiences here. Kissing fails have never disappointed.

#13: What type of girls do you get shy around?

Again, being in this category would be such a huge plus for you. Guys like girls who make them blush, though they will never admit it.

#14: Where and when have you ever had the most uncomfortable sexual experience?

Unearthing all those crazy weird escapades might be one way to brighten up your day and knowing your partner/ friend better. This should be a must-ask.

#15: What is the main thing that gives you butterflies around new girls?

Beware of guys who don’t get butterflies at all. They are most likely to break your heart. Kidding though. Everyone has been made differently.

#16: Assuming I was in the last dirty dream you had, would it be better or worse?

Like some seasoning or spicy marinate, you could be the one thing his life needs

#17: What would be your reaction if I sent a nasty photo of me?

This would be better asked in person. His first reaction would tell it all.

#18: Mention some of your guilty pleasures?

If you are the judgy type, you’d better keep off such questions, lest you want to ruin the whole mood of the game.

#19: Would you hold my hand or grab my waist in front of my friends?

It would easily say a lot about the kind of company he keeps, as well as his perception of what you are to him.

#20: Is it fun before food or food before fun for you?

One of the most interesting questions to ask. Best believe any guy would be confused by this. Food before and after would be the ideal answer.


Kenny is the founder and editor-in-chief of TheTalka. He launched the site in 2019.

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