300+ Flirty Questions To Ask A Guy

Flirting is a wonderful way to show interest in a person and start a conversation with someone you like. However, you want to make sure you know how to flirt with confidence so that you're not too personal early on.

And coming up with fun questions to ask him will do precisely that - offer you the chance to show your personality without giving the wrong impression.

So, if you’re ready to give up on old, boring flirting methods and start using flirty questions instead, you’re in the right place! With our list of flirty questions, you’re sure to hit their funny bone, make them laugh, and shake things up in the best possible way!

Read on for a huge list of flirty questions to ask a guy that will have him smiling in no time at all.

Flirty Questions To Ask A Guy

Flirting is a give-and-take activity, meaning that you both come with different expectations and desires. To get the best out of flirting, it’s important to know what you want from it or what desired outcome you are hoping for.

So, find the right flirty question and watch him light up! The increased levels of emotions can make any situations seem more exciting and interesting.

How do you like to relax in your free time?
What do you do on weekends?
Do you have any morning rituals?
Why is such a cute guy still single?
What is the bravest thing you've ever done?
How do you like to be kissed?
Where would you like us to go for a weekend?
What do you like best about me?
How would you describe yourself in 3 words?
Do you often flirt with girls?
What is the craziest thing you've ever done?
What type of music do you like?
Do you have a favorite song?
What wins you over more, being smart or being sexy?
What is your favorite childhood memory?
How do you decide whether to trust someone or not?
Have you ever done something that changed you as a person?
If there was one thing you could change, what would that be?
Do you have any hidden talents, apart from being cute?
What is one thing you feel grateful for?
When was the last time you had a great night out?

Flirty Questions To Ask A Guy On A First Date

You’re just starting to get flirty with a guy, and you are unsure how to proceed?

Use the following questions to keep the ball rolling. Most guys appreciate it when a girl is playful and flirty since it helps chemistry to develop.

Don’t be afraid to ask some slightly uncomfortable questions! But make sure they are all in good humor and meant to add something fun into your connection!

And remember, the more you become comfortable and enjoy these flirty questions, the more you'll be able to make the most out of each date.

So, let’s get to it!

How traditional are you?
What type of girls do you like?
Have you ever been friends with someone first and then started dating them?
What’s the first thing you notice about a girl?
What's your opinion on one-night stands?
How romantic are you?
When did you first fall in love?
Do you think guys should always make the first move?
What do you think of love at first sight?
Do you believe in monogamy or open relationships?
How old were you when you had your first kiss?
When was the last time you had a girlfriend?
Have you ever cried over a girl?
What is your idea of a romantic date?
What was your longest relationship?
Do you think that being friends first is important in a relationship?
What do you look for in a partner? And why?
What do you seek in a partner?
What turns you off in a relationship?
Would you ever forgive infidelity?
Have you ever cheated on your girlfriend?
What turns you on?
How do you seduce women, and how would you seduce me?
Do you believe in long-term relationships?
Do you think men should always make the first move?
Are you jealous?
What turns you off in a woman?
Have you ever tried skinny-dipping?
Do you prefer to talk over text or in person?
What do you think of kisses on a first date?
Have you ever dated a friend?
Are you friends with any of your exes?
Do you believe in happily ever after?
What was the shortest relationship you've ever been in?
What was your first impression of me?
Do you believe in marriage?
Would you like to have kids?
Have you ever been in a long-distance relationship?
Do you like writing love notes?
What do you prefer, texts or calls?
Have you ever lied about your age?
Do you believe in horoscopes?
Have you ever been on a blind date?
Do you believe in a second chance?
Do you notice perfume on a girl?

Flirty Questions To Ask A Guy Over Text

If you recently met someone and hit it off, asking flirty questions over text messages is an excellent follow-up to ensure you maintain and build on any romantic connection.

Related: How to flirt over text?

If you are worried that you'll overstep the boundaries, here are some questions you can use to make sure you flirt safely. Using emojis will make the conversation more exciting and playful and set the tone for what's to come in the conversation.

It's late, and I guess you're ready to go to bed. What do you wear to sleep 🙃?
If you're reading this, you know I'm thinking of you. What are you thinking about right now 😉?
Do you know what I like about you? I'll give you a hint. You have it right now, and it starts with "s" 🤗. (smile)
Do you like cuddling 💑?
Do you wanna know what I dreamt about last night😉?
Would you say "no" if I invited you to come over🤫?
Since I started thinking about someone, it really became hot in here😓. Do you know who I'm thinking about😛?
I traveled last night far away. Did I drop by in your dreams?
Guess what I have planned for us tonight😈...
Do you like when I am naughty or nice?
How do I fit into your plans for the weekend 👩?
I could really use a drink. Would you like to join me🧉?
I'm ready to take a shower, and it seems I miss something. Can you guess what? And it isn't soap😉.
What would we be doing if we were together right now😉?
Would you like to continue our conversation in person 🙂?
So, now that I have texted you, what happens next👁?
Can you be my gift for Valentine’s Day🎁?

Flirty Questions To Ask A Guy You Just Met

You've just met a guy you like and would like to flirt with him, but you don't know how? Fear not, because here are some flirty questions to ask boys that will make any guy's heart flutter!

Do you like going to the gym?
What is your favorite book?
Can you recite a line from your favorite poem?
Are you fond of massages?
Which side of the bed do you prefer?
Are you a night owl or an early bird?
Do you like surprises?
What is your favorite food?
How do you imagine our first date?
What are you good at?
Is there something you would never do, not even for a million dollars?
Do you have guilty pleasures?
What makes you feel comfortable around a person?
Do you have any long-term ambitions?
What is the nicest thing someone did for you?
What are you doing this weekend?
If you wanted to do a tattoo, where would you get it?
What would you do to win me over?
What book title best describes your life so far?
Who made you the person you are today?
Do you prefer having a shower together or swimming together?
Have you ever deliberately canceled a date?
How important is it to make a good impression?
Is it possible to find true love more than once?
So, will you buy me a drink?
How adventurous are you?
What type of instrument reflects your personality?
Do you like girls with or without make-up?

Flirty Questions To Make Him Laugh

Asking flirty questions can evoke different reactions. In case you want to get a few giggles out of your guy, then these questions are a perfect choice.

Who is your favorite celebrity?
Who was your first celebrity crush?
What is the craziest thing you did for your girlfriend?
What was the most embarrassing thing you did?
Would you rather stay home with your girlfriend or go out with her?
Do you know your body spells the word "muscle"?
What is your favorite romcom?
Have you ever cried over a movie?
What is the worst pick-up line you've ever heard?
What is your ideal type of woman?
How would you react if I kissed you now?
What is your idea of a perfect date night?
How do you like calling your relationship?
Do you know you have the cutest smile?
I really like your haircut. Can you give me your hairdresser's number?
What do you prefer, hugs or kisses?
What do you think my lips taste like?
Have you ever visited a nude beach?
Would I be on your bucket list?
Would you take me to a deserted island?
What was your first kiss like?
Do you like naughty or nice girls?
How would you surprise your girlfriend?
Have you ever done something foolish and got caught in the act?
Will you ask me out any time soon?
Do you like kissing on the beach or in the rain?
I wonder how it feels to kiss you. Will you help me find out?
What was your first time like?
What movie title best describes your love life?
Do you smile when you think of me?
If we could travel together, where would we go?
Aside from existing, how else do you make a difference in the world?
Which portion of my body would you examine first if you had x-ray glasses?
What's your idea of being naughty?
What would your parents say about you if I asked them?
How old were you when you lost your virginity?
What is your worst sexual experience?
What was the strangest place you've ever done in?
Do you like to be controlled or the controlling one in bed?
When was the first time you imagined me naked?
What is your favorite sex position?
Have you ever had friends with benefits?
Do you like biting?
What is your love language?
What nickname did you have when you were younger?
Have you ever been caught watching porn?
Do you prefer quick or slow sex?
Where do you like being touched?
Have you ever sent a nude picture of yourself?
Do you like doing it in the morning, afternoon, or night?
What was your worst kiss experience?
What would you ask me if you knew the answer was “yes”?
Do you sing in the shower?
What would you call me if you had to pick a nickname for me?
Did you have any crushes on your teachers?
What was the most embarrassing thing you’ve ever done drunk?
How would you convince me to come home with you tonight?
What is your opinion on spanking?
Do you like whipped cream in the bedroom?
Would you be embarrassed if I could read your mind right now?
How long could you manage without your phone?
Lights on or off?
Is that a pistol in your pocket, or are you happy to see me?
Have you ever worn a girl’s clothing?
What kind of meal would you cook for me?
Do you prefer giving or receiving?

Flirty Questions To Ask Your Boyfriend

What if you never asked your boyfriend a question like one of these in your life? You might as well just take that chance to ask him now and make your flirting experience unforgettable!

What was the first thing you liked about me?
Do you find me attractive?
What is something you would never like to change in our relationship?
What is your fondest memory of us?
Do you think I am a good girlfriend?
What do you like about my body?
If I could be a flower, what flower should I be?
What is something you would like us to do together?
If I was a Disney character, what character would I be?
Is there a celebrity I remind you of?
Would you like me to be a mother of your children one day?
How many kids would you like to have with me?
Is there anything new you would like us to try in the bedroom that we haven’t tried yet?
What is something I do that makes you feel appreciated?
Have you ever dreamt of us getting old and having grandkids?
What song would you dance to at our wedding?
Do you prefer seeing me in lingerie or a birthday suit?
What do you like most about our relationship?
Is there something I don't know about you, and you've always wanted to tell me?
What quality of mine would you like our baby to have?
Do you have a secret fantasy you would like me to fulfill?
What was something you learned from your past relationships that made ours stronger?
What is something you like me doing to you when we make love?
Do you think you are a good boyfriend?
Do you like when I talk dirty?
What was our biggest challenge as a couple?
What is your favorite foreplay?
Blindfolded or handcuffed?
How do you picture our honeymoon?
What holiday memory should we recreate?
What was your last naughty dream about me?
When was the last time you were jealous of me?
Where do you see us in 5 years?
What's your favorite role-play?
Would naughty things would I find in the search history of your web browser?
How would you propose to me?
What is the first thing you think of when you wake up next to me?
Were you nervous when you first talked to me?

Subtle Flirty Questions To Ask A Guy

Think of these questions as tools to help you have fun, spark conversations, and flirt with a guy you like with ease.

You never know where those conversations will lead, but the payoff is worth the laughter and enjoyment!

In your opinion, what do women want?
How long does it take to realize you have fallen in love with someone?
What’s the nicest thing I could do for you?
Do you believe that a man and a woman can just be friends?
What do women seek in men?
Is there something you are afraid of and you don't mind sharing?
If a fairy granted you three wishes, what would those wishes be?
What's your favorite superpower?
What do you like more, cats or dogs?
Is there something you would like to ask me?
Is there someone you think of before you fall asleep?
What does always cheer you up?
Is there something you can never resist?
How far would you go on a first date?
What do you think of women who like to flirt?
What is your idea of a perfect kiss?
How would you describe me to your friends?
What's the worst date you've ever been to?
If you could spend an entire day with me, what would we do?
Would you be ready to leave your job just to be with the person you love?
Which outfit color would suit me?
What is the funniest joke you've ever heard?
What hobby would you take up with your girlfriend?
What types of compliments do you like receiving?
What is the craziest thing you have ever done to catch a girl's eye?
What type of clothes do you like best on women?
What can a woman do to win you over immediately?
What does commitment mean to you?
Should partners keep secrets from one another?
Do you have a preference when it comes to a girl?
Do you like kissing with your eyes open or closed?
Are you ticklish?
What do you think of sexting?
How close would you like us to go?
What is the first thing that comes to your mind when you see or hear me?
What would you compromise in a relationship?
Is there anything in your past that you regret not doing?
Have you ever broken the law?
What song would you like to dance to with me?
What number of sexual partners is too much for you?

Flirty Questions To Ask A Guy To Get To Know Him Deeper

What better way to show interest in a guy and get to know him better than the delicate and flirtatious banter of flirty questions?

Keep these questions in mind to use on your crush or a date. That way, you'll get him more interested in you. Plus, you’ll discover what you have in common.

Do you consider yourself ambitious?
What gives you pleasure?
Is there something you would like to achieve in the future?
What is your secret obsession?
Do you believe in destiny?
What do you like doing on a rainy day?
How do you wind off after work?
Is there someone you admire in your family?
Does being successful matter to you?
Is there something you can never forgive yourself?
Is there something you could never forgive a person?
Can you name three qualities your girlfriend needs to have?
Do you have someone in your life you can always rely on?
Would you date a girl your family disapproves of?
Would you like to become famous and what for?
What is something you are really proud of?
Do you always follow your heart?
How would you introduce me to your parents?
What is something surprising about you?
Would you like to know what the future holds?
Are you an introvert or an extrovert?
What could I do to calm you down if you were feeling nervous?
Where would you like to live with your girlfriend?
Have you ever fallen in love online?
Have you ever had an inappropriate crush?
What do you do when you feel lonely?
Is there a song that makes you think of me?
Who could you spend an entire day with without getting bored?
What do you think is the right age to get married?
Do you ever feel shy around me?
Do you think that your first impression of a person is usually correct?
What game would you like to play with me?
Have you ever dated a girl with a different religion?
How easy do you get emotional?

Fun Flirty Questions To Ask A Guy

Here are some lighthearted and fun questions to ask your guy. Let your skillfulness and wit show as you flirt just the right amount to keep him coming back for more.

Have you ever laughed so hard that you actually peed your pants?
Do you like truth or dare?
How funny do you think you are?
Would you mind me kidnapping you?
Do you prefer fun or deep questions?
Would you rather have me think of you as smart or sexy?
Where would you like me to kiss you?
Who do I have to kill to get your phone number?
Apart from being handsome, what's another best compliment you've ever received?
If a black cat crossed your way on your way to meet me, would you turn back?
Do you think your dog will like me?
Have I ever done something that made you want to disappear from the face of Earth?
I heard that kissing is better than exercising. Wanna check that theory?
What else do you do if someone annoys you apart from hypnotizing them with your smile?
How short am I from being incredible?
Do you see me as a friend or something more?
What would you do if you caught me undressing?
If you were a woman for one day, how would you spend it?
Which would you rather have, a month without sex or a month without TV?
If you could choose one celebrity as a friend, who would that be?
Have you ever drunk-dialed someone?
Do you enjoy breaking girls’ hearts?
What’s your favorite curse word?
How much time do you need to get ready in the morning?
What is the cheesiest break-up line you’ve ever heard?
What is the most embarrassing thing your parents saw you doing?

Related: How to get a boyfriend?

Conclusion

Being flirty is easy when you know the right questions to ask a guy! And with this list, you'll have all the questions you need to tease him and have him on the edge of his seat.

Confidence is also crucial here, so don't be scared to ask. With a lovely, sweet-sounding voice, and the best flirty questions up your sleeve, you'll have fun and blow his mind in no time!

Good luck with your flirting!

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