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153+ FUN Flirty Questions to Ask a Guy You Like!

Going on a hot date night? Fabulous! Here are 153+ Flirty Questions to ask a guy that just might come in handy!

Welcome to the world of flirty curiosity and playful banter! The journey of getting to know someone you’re attracted to can be both exciting and nerve-wracking.

Whether you’ve just met a fascinating guy or you’ve been crushing on someone for a while, there’s no denying that you can learn some cool stuff with some flirty questions. These seemingly innocent yet subtly enticing queries can help you break the ice, establish a deeper connection, and perhaps even pave the way for something more enchanting.

Flirting is an art, and just like any other art form, it takes practice and a touch of finesse to master. But fear not, for in this blog post, we’ve gathered an array of captivating flirty but fun questions that will not only make him smile but also make him eager to unravel the mystery that is you.

While flirting is a great way to express your interest in your partner, it’s also about building a rapport and creating a comfortable atmosphere for both of you to open up.

The right question, asked at the right moment, can light up sparks of excitement and make your conversation unforgettable. Whether you’re looking to spice up a date night, reignite a long-term relationship, or simply explore the possibilities of a newfound connection, these questions are here to inspire and infuse your interactions with charm and charisma.

So, if you’re ready to embark on an adventure of playful questioning and sincere interest, let’s dive into a handpicked selection of flirty questions to ask a guy. Remember, the key is to be genuine, have fun, and enjoy the process of discovering the intriguing layers of each other’s personalities.

Buckle up your seatbelt as we unlock the secrets to flirty interrogation, and get ready to unleash your inner flirtatious goddess!

You might even like to use some of these flirty questions as flirty texts for him later! Possibly even as some fun Tinder Pick up Lines

153+ Flirty Questions to Ask a Guy

It can be so hard to know what to say when going on a date. Here are some flirty questions we thought of to avoid the conversation getting awkward at all!

Oh, by the way, If you are looking for a sweet date idea to ask these questions, here are some of our best ideas:


Questions About You

Let’s face it, you are dying to know what he thinks of you, AmIRight? With these flirty questions, you will get to know exactly what he thinks of you

What would you say are the aspects that draw you to me?

Name 3 of my body parts that you like the most?

What color do you think would look best on me?

If I was a flower, what kind of flower would I be?

What is something that you think sets me apart from other people?

What famous actress do you think I’m most like?

Do you like my outfit?

What do you think is my favorite food?

If we were to go on another date, where would you take me?

What is refreshing about me?

If you prefer a “Question Game” that does the hard work for you, here some of our favorites you could pick up:

Questions About Him

A good date always comes with a mixture of questions about yourself and him, so here ares some flirty questions to ask about him!

  1. What is your favourite body part?
  2. What do you like most about yourself?
  3. What is the kindest thing you have ever done?
  4. What is the proudest moment of your life?
  5. Would you consider yourself a romantic?
  6. Do you consider yourself a feminist?
  7. What is your favorite childhood memory?
  8. So, do you work out or what?!
  9. Do you prefer bars or clubs?
  10. What are you most afraid of?
  11. If you could ever be really smart or really good looking – which would you pick?

If you are looking for a few more like this, here are 21 fun questions to ask a guy!

Flirty Love Questions

Love! Well that’s the whole reason why we are here, on this date! So might as well get some good answers out of it!

  1. Do you believe in love at first sight? (Or should I walk by you again – no just kidding on the last part lol)
  2. What do you see in your future?
  3. Do you believe in fate or destiny?
  4. What does love mean to you?
  5. What is your favourite romantic movie? (And don’t pretend you don’t have one. Oh, and don;’t say the Notebook because I’ll know that is a lie!)
  6. Do you see me falling for you?
  7. What do you think is the best pick up line?
  8. What do you think is the worst pick up line?
  9. Have you ever used a pick up line to get a girl?
  10. Love or money? (If he picks money – RUN!)
  11. Describe your ideal relationship?

You might also like would you ever questions for couples.

Past Relationships

This can be a very awkward topic but it’s just something that you gotta know so let’s ask the questions as a total flirt! Is there really any other way!?

  1. What qualities do you look for in a girl?
  2. What was the shortest relationship you have had?
  3. What is the longest relationship you have ever had?
  4. What is the most romantic thing you have ever done?
  5. Did she think you were a romantic?
  6. Do you think you would make a good boyfriend?
  7. Why did your last relationship end?
  8. What is a deal breaker in a past relationship?
  9. What did your last relationship like most about you?
  10. What did your last relationship dislike most about you?

You might also like flirty questions to ask your crush

Questions About Sleep

  1. Do you like sleeping in or are you an early bird?
  2. Do you like cuddling?
  3. Are you a blanket hog?
  4. What kind of pillow is your favourite?
  5. How well do you sleep in hotel rooms?
  6. you prefer being the big spoon or the little spoon?
  7. Are you a light sleeper?
  8. What was your worst nightmare?
  9. Do you often have dreams?
  10. Do you snore? If yes RUN GIRL RUN!

You might also like love messages for him

Cheeky Flirty Questions to Ask a Guy

These ones are a little cheeky but hey if you are game, go right ahead! Go girl go!

  1. What would you do If I kissed you right now?
  2. What is your biggest turn on?
  3. What is your biggest turn off?
  4. Do you prefer cuddling or kissing?
  5. What are your favourite pet names for girlfriends? Babe, Cutie etc. Which don’t you like?
  6. Want to know a secret?
  7. Who was your teacher crush?
  8. There is just something about you, I can put my finger on. Do you know what it is?
  9. What do you wear to go to sleep?
  10. I just want to know how on earth are you still single?
  11. Do you have a secret fantasy?
  12. Do you have a foot fetish? (Sorry I just had to find out if you had been on Jerry Springer)


Random Flirty Questions to Ask a Guy

Okay some random questions for you girl:

  1. What are you thinking about now?
  2. So… do you have plans this weekend or?
  3. What do you think I am thinking about right now?
  4. How you doin’? (Our friend Fabio would use this one)
  5. What is your type in girls?
  6. When was the last time you experienced butterflys?
  7. You really don’t know how cute you are, do you?
  8. Do you know you have the most amazing eyes? What color are they?
  9. Would you say I am your usual type?
  10. Do you like hugs?
  11. If you have 3 wishes, what would they be?
  12. Do you believe in having a soul mate?


Fun Questions

Okay just some random, fun flirty questions to ask him:

  1. When was the last time you laughed so hard you cried?
  2. Have you ever peed your pants (be honest!)
  3. Would you rather still be friends with an ex or never talk to them again?
  4. Would you rather jump into a pool of custard or apple pudding?
  5. Are you a fan of public displays of affection?
  6. If we were stranded on a desert island, what are 4 things we should bring?
  7. If you died, would you rather your spouse marry your best friend or someone you hated?
  8. Would you rather dance in a club or under the moonlight?
  9. Truth or dare?
  10. How many days have you gone without changing your underwear? (BE honest)
  11. Would you ever do a nudie run?
  12. Would you ever visit a nude beach?

Cute Questions

Too cute to be true! Here are my fav cute questions to ask a guy:

  1. Do you think you are a reliable person? What is the most reliable thing you have done?
  2. Are you funny? Tell me a joke and i’ll be the judge!
  3. So, why is it worth taking a chance on you?
  4. Are you a heartbreaker?
  5. Stater, main or desert?
  6. Would you cook for a girl?
  7. If you could have one superpower what would it be?
  8. If you had to pick either coffee or tea to drink forever, which would it be?
  9. What is the cutest thing you have ever done?
  10. What is the kindest thing you have ever done?

Flirty Would you Rather Questions

  1. Would you rather a day at the beach with me or a day skiing?
  2. Would you rather 1 million dollars or finding the love of your life?
  3. Career or love?
  4. All girls as kids or all boys?
  5. Orange or Purple?
  6. 24 hours of sunlight or 24 hours of moonlight?
  7. Would you rather chocolate or lollies?
  8. Would you rather your dream girl or fame?
  9. Would you rather starbucks or a little coffee shop?
  10. Would you rather fall or spring?

Questions About Life

Here are some very important flirty questions to ask a guy about life:

  1. Do you ever think you’d be a baby daddy?
  2. How many kids do you see yourself having?
  3. What do you think your family and friends would say about me?
  4. Do you prefer dogs or cats?
  5. Tell me something that I don’t know about your life?
  6. What are 3 most important things on your bucket list?
  7. What is your first memory?
  8. Have you ever thought of an age you would like to be married by?
  9. What does marriage mean to you?
  10. Could you marry someone outside your faith?
  11. What is your favourite memory?
  12. Where do you see your life in 5 years time?
  13. What is the worst thing that ever happened to you?
  14. Would you rather be rich or famous?
  15. If you won 1 million dollars, how would you spend it?

Questions About Entertainment

Entertainment is very important. If your entertainment preferences don’t align, dare I say it, this might just be over before it has even begun!

  1. What is your favourite way to relax?
  2. Are you a Netflix Guy?
  3. Do you prefer bars or clubs?
  4. Do you prefer to work out in a gym or outside?
  5. Do you like to watch tv alone or with a partner?
  6. What type of music do you like?
  7. What song would you dance to at your wedding?
  8. Who is your female celebrity crush?
  9. Who do you think is the hottest male celebrity? (You have to pick ;))
  10. Would you ditch your girlfriend if you celebrity crush wanted a date?

Flirty Questions About Food

As a self-described foodie, here are some very important questions about food to ask your potential new soul mate:

  1. What is one food you can’t live without?
  2. Is there any food you would give up a relationship for?
  3. What food do you dislike the most?
  4. Do you like whipped cream?
  5. Would you be into body paint?
  6. Would you consider yourself a foodie?
  7. How would you feel if a girl was a bigger eater than you?
  8. If you had to eat one food for the rest of your life what would it be?
  9. Do you believe in aphrodisiacs?
  10. What would be your green mile meal? 

Questions About Travel

In my opinion, a guy who likes to travel is a keeper. Or, you might think the opposite. But it is great to know if your thought on travel align:

  1. Would you say that you are an adventurer?
  2. Are you a homebody or an explorer?
  3. Do you prefer to explore locally or go on an overseas trip?
  4. Could you be with a girl who didn’t want to travel?
  5. If we could time travel, to what age or era should we go?
  6. Would you rather go to space or to another country?
  7. What country is at the top of your bucket list?
  8. Would you travel to another country and live there for love?
  9. If you could have your dream job, but it was in another country, would you go for it?
  10. China or India?
  11. What is your worst trait when traveling?

More Flirty Questions

  1. What’s the most spontaneous thing you’ve ever done, and would you do it again with someone special?
  2. If you could take me on a surprise date, where would you whisk me away to?
  3. What’s your favorite way to unwind after a long day? Care to share the experience?
  4. If we were to dance together, what song would you want to slow dance to?
  5. Do you believe in love at first sight, or should I walk by again?
  6. What’s the most romantic gesture you’ve ever made for someone, and could you see yourself doing it for someone you really like?
  7. If you could pick any place in the world to share a kiss, where would it be?
  8. What’s your idea of a perfect date night, and would you let me plan one for us?
  9. If you were a superhero, what superpower would you use to impress me?
  10. What’s the sweetest compliment you’ve received, and could you handle one that’s even sweeter?
  11. If we were at the beach right now, what fun activity would you suggest we do together?
  12. What’s something you’ve always wanted to try, but you’ve been waiting for the right person to do it with?
  13. If we were in a room full of people, would you make it obvious that you’re interested in me, or would you play it cool?
  14. What’s the most daring thing you’ve ever done to win someone’s heart?
  15. If you were a character in a romance novel, how would you sweep the heroine (me) off her feet?


So what did you think of our ultimate list of Flirty Questions to ask a guy? Did you find something juicy to ask?

If you are already married, you may find some better questions in our questions for married couples. You also might enjoy our Never Have I Ever Questions for Couples or Who is more likely to questions for Couples.

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  • MC Miller

    MC Miller is a travel blogger and writer who has travelled America extensively and abroad to over 80 countries. He founded Couple Travel The World in 2017. Since then, he has spent over 6 years on the road as a full time travel couple. When he not traveling he likes to spend quality time with his partner Bett, planning our their next date or romantic getaway!

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Saturday 12th of August 2023

Love love love this. Gonna try it on my guy tonight


Sunday 18th of September 2022

Very helpful