200 Flirty questions to ask a guy that will totally have him flirting back with you. Perfect for the guy you just met, 20 questions with a crush or your boyfriend.

200+ Flirty Questions To Ask A Guy (& Be Irresistible)

200 Flirty questions to ask a guy that will totally have him flirting back with you. Perfect for the guy you just met, 20 questions with a crush or your boyfriend.

There’s nothing like the thrill of a flirty conversation to make you feel like you’re on cloud nine. When that back and forth banter is just working. Whether you’ve just met that guy or have been together awhile. It’s arguably one of the best feelings of all time!

But sometimes sustaining all that flirty banter can need a little inspiration. Which is where we come in. 

We’ve compiled a list of not just 100 but 200 flirty questions to ask a guy. Which you can use to help you keep the fun and juicy conversation flowing.

40 Flirty Questions To Ask A Guy

In the list below, you’ll find good flirty questions to ask a guy you just met, just started dating or your crush. Along with some that are perfect for your boyfriend too.

You can also throw these questions out at anytime in person, on a date or while texting a guy. Or you can use them to start an impromptu fun and flirty game of 20 questions

200 Flirty Questions To Ask A Guy

Whether you’re on a first date or have just met a new man, amping up the flirtiness factor of a conversation doesn’t have to be hard. You just need to know how to ask him the right questions. Use the following questions to get the conversation flowing in a lively direction. And soon you’ll see if there’s any chemistry there.

Flirty quotes and questions for him

40 Flirty Questions To Ask A Guy

If you’re looking for some good flirty questions to ask a guy, then you are in the right place! The playful questions below are a great way to get the conversation started:

  1. Would you rather be considered sexy or smart?
  2. What is something about you that would surprise me?
  3. What did you first notice about me?
  4. What was your first kiss like?
  5. What’s one question you’re dying to ask me?
  6. How many times have you been in love?
  7. What do you think about before you fall asleep?
  8. So what do you think we should do this weekend?
  9. Do you enjoy being in a long term relationship?
  10. If yes, what do you most like about being in a relationship?
  11. If you could be famous for anything what would it be?
  12. What’s a gift you’ve always dreamed of receiving?
  13. When are we going on our next date?
  14. What puts you in a good mood?
  15. Would you rather that I was naughty or nice?
  16. Have I made it into any of your dreams yet?
  17. What is a favorite movie of yours that I would be surprised that you like?
  18. What wins you over more… brains or beauty?
  19. Would you rather end a date with a kiss or with a little bit of mystery?
  20. What have you always imagined doing with a girlfriend that you’ve never done?
100 Fun And Flirty Questions To Ask A Guy

Fun And Flirty Questions To Ask A Guy

With fun questions like these on hand, you’ll never run out of things to talk about with him. For the best list of fun and flirty questions to ask a guy in person or over text check out this list below:

  1. If you had to use one movie title to describe your kissing style what would it be?
  2. Little spoon or big spoon?
  3. What is one temptation you can never resist?
  4. How would someone usually let you know that she likes you?
  5. Do you like a woman that is soft and sweet or more assertive?
  6. How would you describe yourself in 3 words?
  7. How would you describe me in 3 words?
  8. Do you prefer staying in or going out?
  9. What do you think your best feature is?
  10. Have you ever made a really romantic gesture?
  11. Would you rather date someone smart or hot?
  12. How many people are you crushing on right now?
  13. What’s the farthest you’ve gone on a first date?
  14. What did you think when you first saw me?
  15. What’s your biggest turn off?
  16. What’s your biggest turn on?
  17. Do you like when a woman flirts with you?
  18. Did you do anything interesting today, well besides talking to me?
  19. Who would you want to play your love interest in a movie about your life?
  20. If we went on a date, what would it look like?
Flirty Questions To Ask A Guy You Just Met

Flirty Questions To Ask A Guy You Just Met

Fun and flirty personal questions are a great way to get to know a guy you just met. Use the following questions to keep the conversation playful and innocent, yet still intriguing. Try slipping these into your next conversation to see if there is a spark. And perhaps even take things to the next level!

  1. What’s the first thing you notice about someone when you meet them?
  2. Do you think guys should always make the first move?
  3. How would you imagine our first date?
  4. Do you prefer to talk over text or do you prefer to talk in person?
  5. First-date kisses: Yay or nay?
  6. Who was your first crush?
  7. Do you believe in love at first sight?
  8. What was it like the first time you fell in love?
  9. What are your top five things to do on weekends?
  10. How did you get to be so good at (insert X activity here)?
  11. Do you believe in monogamy or open relationships?
  12. Do you consider yourself a romantic?
  13. If you could star in a movie what movie would it be?
  14. What would you never do for a million dollars?
  15. What is the bravest thing you’ve ever done?
  16. If we could get on a plane to anywhere right now, where would you like to go? Why?
  17. Do you think that being friends first is important in a relationship?

Related – 130 Flirty Text Messages To Send To A Guy You Just Met (The Best Examples)

Subtle Flirty Questions To Ask A Guy

If you don’t want to come across to obvious or over the top, yet you want to see if there’s some potential for things to get a bit more flirtatious. Then no worries, we’ve got you covered. Starting a conversation is easy, with these semi-flirty and subtle flirty questions for him.

  1. What’s the craziest thing you’ve ever done for someone while you were dating them?
  2. What famous person do you find yourself crushing on the most?
  3. Who do you go out of your way to be nice to?
  4. What is your idea of a great date night
  5. Would you rather watch a movie or watch the sunset?
  6. Do you have a type?
  7. What makes you feel comfortable around someone?
  8. What’s the most important thing in your life right now?
  9. What are your best qualities?
  10. What’s your favorite way to flirt with a woman?
  11. What’s the nicest thing someone could do for you?
  12. What is one of your guilty pleasures?
  13. Have you ever dated one of your friends?
  14. How do you know when you’ve fallen for someone?
  15. What sounds like more fun to you, a picnic under the stars or dinner at a romantic restaurant?

Related – 120+ Flirty Good Morning Texts For Him

20 Questions To Ask A Guy

20 Questions To Ask A Guy

Starting a flirtatious game of 20 questions is a great way to initiate a fun conversation with a guy you like. Ask him one of the random personal questions below to get your playful discussion underway.

  1. What do you think your best feature is?
  2. Are you more likely to fall in love with your head or your heart?
  3. Do you think you make a good boyfriend?
  4. What’s your favorite thing about me?
  5. Truth time, what’s the worst pick-up line you’ve ever used?
  6. Do you prefer casual dating or being in a long-term relationship?
  7. Where’s your favorite place to be kissed?
  8. What’s your idea of a perfect date?
  9. Am I your usual type?
  10. What’s the most romantic thing someone has ever done for you?
  11. What are you like as a boyfriend?
  12. What do you expect from a girlfriend?
  13. What makes you fall in love with someone?
  14. If you could spend an entire day with me, what would we do?
  15. What excites you?
  16. In 5 words, what’s your ideal type?
  17. What’s better – naughty or nice?
  18. What’s the best advice you’ve ever received?
  19. Do you believe in love or lust at first sight?
  20. What habit do you have that you’re most proud of?

Looking for some more good flirty texts, then check out my article here > Flirty Texts To Make Him Laugh

Flirty Would You Rather Questions

Flirty Would You Rather Questions

There’s nothing like having a few great flirty would you rather questions on hand to get an interesting conversation started with a guy. It’s also excellent way to keep the banter going. While never running out of things to talk about. Would you rather questions are also a handy way to break the ice on a first date.

While yes, these questions are mostly for fun. They can also tell you a lot about the other person. By way of giving you some insight into whether you’re compatible with him or not.

  1. Would you rather be twice as intelligent as you are right now or twice as attractive?
  2. Where would you rather spend time at the corner pub or a nightclub?
  3. Would you rather kiss in the dark or kiss in the rain?
  4. Would you rather give or receive a gift?
  5. Would you rather rather stay friends with your ex or never talk to them again?
  6. Would you rather still be friends with an ex or never talk to them again?
  7. Would you rather love and lose, or never love at all?
  8. Would rather have endless money or endless love?
  9. Would you rather be snowed in with your crush or stranded on a beach with your crush?
  10. Would you rather find true love or be rich?

For more flirty would you rather game questions (that also can double as flirty questions to ask on Tinder) check our article here >> 150+ Flirty Would You Rather Game Questions (Witty, Fun, Funny, For Him or Her)

21 Questions To Ask A Guy Over Text (Or In Person)

21 Good Questions To Ask A Guy Over Text (Or In Person)

Looking for something personal to text him? Guys love getting flirty texts that set the tone of the conversation up for playful banter. To up your flirting factor don’t forget to add in a few emojis and gifs. Which will help to make sure that these texts come across with with right context and tone.

  1. Finally watching Love Is Blind and I have so many thoughts. Do you think you could ever fall in love with someone without having seen them first?
  2. What would we be doing if we were together right now?
  3. This is me asking you out. Want to get coffee on Saturday?
  4. Our first kiss is going to be epic, don’t you think?
  5. What would you say if I asked you to come over?
  6. Which emoji makes you think of me?
  7. What is the best and worst pick up line that you have ever heard or used?
  8. I like you. What are you going to do about it?
  9. Want to have this conversation in person?
  10. Which meme best represents your life right now?
  11. So now that I have your number, what’s next?
  12. Miss me yet?
  13. What do your weekends look like, and how do I fit into them?
  14. Good Morning! Curious what I dreamt about you last night?
  15. What are your 5 most frequently used emojis?
  16. Is it hot in here, or is it you?
  17. Guess what emoji I put next to your name right now on my phone?
  18. Have you ever dreamt about me?
  19. Have you ever accidentally sent an embarrassing text?
  20. What would you be doing to me if we were together right now?
  21. Wanna know a secret?

For more flirty questions to text a guy check out our post here – 120+ Flirty & Irresistible Texts To Send To A Guy You Like

20 Questions To Text A Guy or Ask In Person

20 Flirty Questions To Ask Your Crush

Spice up your next conversation by asking your crush these 20 flirty questions. Besides being perfect for playing a game of 20 questions with a guy you like. They’re also good to have on hand so that you’ll never run out of things to ask him. In addition to also being very telling. The answers you get may even reveal all sorts of interesting tidbits about him that you never expected.

  1. What is your stance on a woman making the first move?
  2. What’s the best compliment you’ve ever received?
  3. What’s the first thing that you always notice about a girl?
  4. What’s your idea of a perfect kiss?
  5. What were you like when you were a kid?
  6. Would you rather kiss on the first date or wait until the second date?
  7. What’s the weirdest pet you would like to have?
  8. What do you think my favorite type of food is?
  9. What’s the perfect way to ask someone out?
  10. Would you rather post an awkward picture of you from middle school or the last 3 photos that you took with your phone?
  11. What’s your biggest deal breaker on a date?
  12. What qualities do you look for in a woman?

Receiving a cute good morning text from someone you’ve been dating or crushing on is always a cool feeling for ideas on what to text them check out our list of Flirty Good Morning Texts For Your Crush (Him/Her).

Flirty Questions To Ask A Guy Over Text

Below you’ll find some fun, random, and flirty questions to ask a guy over text:

  1. What would you do if I kissed you?
  2. How would you describe me to your friends?
  3. What’s your favorite pick-up line?
  4. What are you superstitious about?
  5. Which 3 qualities in a woman do you find the most attractive?
  6. What are your 3 most attractive qualities?
  7. Do you believe everyone has just one soulmate or multiple soulmates?
  8. If you ever wanted to disappear, where would you think about going?
  9. What are you most passionate about?
  10. If you had to eat only one food for the rest of your life what would you choose?
  11. If you could change one thing about yourself, what would it be?

Deep Questions To Ask A Guy (Next Level)

Want to get to know your guy on a deeper level but aren’t sure what to ask? We’ve put together a list of meaningful personal questions and romantic questions to help spark a great conversation about anything and everything. Use these on a crush, a guy you just met, or are dating. These are also good flirty questions for couples too.

  1. What does love mean to you?
  2. What do you think about open relationships?
  3. What makes you truly happy?
  4. What was the shortest relationship you’ve ever had?
  5. What was the longest relationship you’ve ever had?
  6. What’s been your biggest regret in life?
  7. If you can change one thing about yourself, what would it be?
  8. Would you consider yourself romantic?
  9. Do you believe in soul mates?
  10. Do you believe in fate or destiny?

Related – Romantic Questions For Couples

100 Flirty Questions To Ask A Guy You Like

Here are some good low key flirty questions to ask a guy you like to get to know him deeper:

  1. What do you remember most about your first love?
  2. What makes you feel accomplished?
  3. What is the most important thing in your life right now?
  4. Could you ever forgive someone that cheated on you?
  5. How important to you is being very successful?
  6. What does success look like to you?
  7. Would you rather move across the world for your dream job or dream girl?
  8. What do you think women want most in a romantic relationship?
  9. What traits in a man do you think are most important to women?
  10. What is your favorite childhood memory?
  11. What’s your funniest childhood memory?
  12. What’s the most romantic movie that you’ve ever seen?
  13. Who is the person in your life that you can always count on?
Juicy & Personal Questions To Ask A Guy

Juicy Questions To Ask A Guy 

If your conversation is going well and you want to spice it up a little, then ask him something a little more playful and extra hot. Ask him a questions from this list of spicy and juicy questions below and let the conversation go where it may. And if you’re already in a relationship. Then these are also great flirty questions to ask your boyfriend.

  1. What do you prefer to sleep in… if anything at all?
  2. Are you a fan of public displays of affection?
  3. Have you ever gone skinny-dipping?
  4. Where’s the craziest place you have hooked up with someone?
  5. If you could only touch me in one place, where would it be?
  6. What are you thinking about right now?
  7. Other than the obvious where do you like to be touched the most?
  8. What color of underwear do you think I’m wearing right now?
  9. If you could re-create any spicy scene from a movie with me, which one would it be?
  10. Where would you like to kiss me?
  11. Where would you like to be kissed?
  12. Would you ever try a body paint date night?
  13. In the mood to have some fun?

Cheeky Flirty Questions To Ask A Guy

If you’re feeling bold and sassy, then why not ask him one of these cheeky flirty questions below:

  1. What turns you on?
  2. What is the most romantic thing that you have ever done?
  3. What is the quickest way to get you in the mood?
  4. Would you rather see me naked or see me in lingerie?
  5. Do you think you’re a good kisser?
  6. Would you ever sleep with your ex’s best friend?
  7. What is the best kiss you have ever had?
  8. I heard kissing burns calories, want to help me exercise?
  9. Do you prefer to give or receive?
  10. What’s your go to favorite song to sing karaoke to?
  11. Do you want to know what I’m wearing?

Related – Cute Goodnight Texts For Him

What To Know When Asking Him Interesting Personal Questions

Cute Flirty Questions To Ask Your Boyfriend

These cheeky questions for your boyfriend are very flirty, cute and a little spicy too:

  1. What’s your love language? 
  2. How do you show your love to someone you care about the most?
  3. What is your favorite memory of us as a couple?
  4. How do you feel most appreciated?
  5. What makes you feel the most cared for and loved by a woman?
  6. What do you hope never changes about our relationship?
  7. Have you ever had a sexy dream about me?
  8. What does the ideal relationship look like to you?

Related – Who’s Most Likely To Questions (For Couples & Friends)

Good Flirty Questions to Ask Your Boyfriend / Husband

  1. What do you find irresistible about me?
  2. How would you like to seduce me?
  3. Do you have a secret fantasy?
  4. Growing up who was your celebrity crush?
  5. Where was the most unusual place that you have ever had sex?
  6. What qualities are the most important to you in a girlfriend?
  7. How would you like to be surprised?
  8. If you could take us anywhere on a dream vacation, where would we go?
  9. What have you learned from some of your past relationships?
  10. What makes you think about me the most?
  11. If you would wave a magic wand what would our dream life together as a couple look like?
  12. What are the top 3 places that you want to travel on your bucket list?
  13. What activity would you like us to do together?

Related – 220+ Questions For Couples Ask Each Other (Before They Get Married)

Flirty & Cute Questions To Ask A Boyfriend

What Are Good Flirty Questions?

The best flirty questions to ask someone you like are open ended questions that have a positive and playful tone which sparks further conversation. The questions can be a bit cheeky or juicy too. As long as you make sure you’re asking them with the right balance of playful tone and context.

How Do You Ask A Flirty Question?

If you’re asking him the flirty question in person. Be aware of your tone of voice and body language. Most importantly don’t forget to smile and make eye contact with him. If you happen to be doing a little flirting over text. Then make sure to add in emoji’s to help convey an inviting and playful tone in your messages.

What To Keep In Mind When It Comes To Asking Flirtatious Questions

It’s important to be mindful of a few things when asking a guy questions. Especially timing, context and tone. Depending on the type of relationship that you have, not every question is going to be appropriate to ask. Sometimes it’s going to be a matter of the right place and the right time.

You also want to bear in mind that these types of questions are meant to be fun. As well as move your relationship forward. So pace yourself and let the conversation unfold naturally. Don’t “machine gun text” him or bombard on the phone or in person, with random question after question. Think flirty back and forth banter.

For tips on how to text guys check out my post here >> 27 Ways To Start A Conversation With A Guy Over Text (+Examples) I also have a list of conversation starters here.

Flirty Questions And Falling In Love 

Getting to know a new guy, or deepening a relationship with one you already have takes time. And asking flirty questions can definitely help create a deeper connection. There is actually some scientific evidence that asking your partner deep questions can move your relationship to the next level. In some cases even helping play a role in two people falling in love. 

As documented in the now infamous study – the 36 questions experiment. Where psychologists, Arthur Aron, Ph.D. and Elaine Aron, Ph.D. conducted an experiment to see if they could create a kind of “short cut” to two people falling in love. By way of a certain set of specific questions

Does it work? In my personal experience as a coach for several years now, the answer is this, it’s really not only about the specific 36 questions. Though they do definitely play their part.

At the end of the day it’s more about how willing each person is to open up to the other. Share themselves in an honest way and be vulnerable with the other person. In addition to the feeling of acceptance that you can be loved for who you really are that comes along with that. 

So keep asking him those flirty questions. After all there are so many options here for you to chose from. And who knows? If you are both willing to open up with each other, you may just be headed toward building something wonderful together.

Happy Flirting! 

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