198 Really Flirty Questions To Ask A Guy

If you’re looking to spice things up with the guy you like, flirtatious questions are an enjoyable approach to enhance your familiarity with him.

Whether it’s your first date or you have been seeing each other for some time, using the right questions helps gauge his personality and determine your compatibility. In this article, we’ve compiled a list of really flirty questions to ask a guy. You should consider using them when getting to know a guy deeper and having some fun along the way! 

Flirty Questions To Ask A Guy

  1. What do you find most enjoyable about me?
  2. Do you know how your smile affects me when we interact?
  3. I’m sure we can come up with some fun ways to get to know each other better.
  4. Wouldn’t it be fantastic if you could be why I smile daily?
  5. What keeps you wanting to chat with me?
  6. Can you make me laugh right now?
  7. If you could be anyone for a day, who would it be and why?
  8. What has been the greatest compliment you’ve ever received?
  9. I would love some insight into your current thoughts.
  10. Do you prefer texting or talking on the phone?
  11. Would you instead go out for a date night or have an in-home cozy evening?
  12. What’s one new hobby or interest that you are exploring?
  13. Can you teach me something new?
  14. How many licks does it take to reach the center of a Tootsie Pop?
  15. Are there any experiences that have piqued your interest, yet you have not had a chance to explore them yet?
  16. Do you have any helpful flirting advice to share?
  17. What’s the most subtle way of showing someone that you’re interested?
  18. Are you competitive, whether in games or real life?
  19. What brings out the smile on your face and gives you that much-needed boost of energy?
  20. What interests do we share?
  21. We should have an in-depth conversation; what do you think?
  22. What potential date ideas do you have in mind?
  23. How can I get to know you even better?
  24. What’s something overly cheesy that you secretly enjoy?
  25. Are there some activities in life you find yourself trying to avoid, perhaps due to not liking them enough or fear of missing out on some exciting experiences? Are these things on your list of must-do’s?
  26. Do you think it’s possible to fall in love with someone without ever meeting in person?
  27. Are there any topics or skills on your mind that have been keeping you from learning more and keeping your curiosity burning strong?
  28. Let’s play a game – truth or dare?
  29. Do you believe in fate, or do you create your destiny?
  30. Can you summarize everything I need to know about you in one sentence?
  31. What do you find attractive about someone else?
  32. What has been your most daring adventure?
  33. Do you have any dating pet peeves?
  34. What would you bring if we were on a deserted island together?
  35. Is there a question that’s been on the tip of your tongue every time we talk, one that you’ve been meaning to ask me but haven’t quite found the right moment for?
  36. How do you like to spend a lazy Sunday with no plans?
  37. Do you believe there’s an ethical difference between flirting and being friendly?
  38. Is there something you’ve been yearning to do for that special someone in your life, a romantic gesture or thoughtful act you’ve wanted to carry out?
  39. What’s the most thoughtful gift you’ve ever given someone?
  40. Do you have any favorite quotes or mantras that guide your daily life?
  41. Do you have some ideas on how to make someone feel truly special?
  42. And finally, what can’t wait until tomorrow morning when the memories will last forever?
  43. Do you believe in the possibility of having an intimate friendship with someone you’re attracted to?
  44. What’s your favorite physical feature on someone?
  45. What would be a creative way to ask someone standing near you out?
  46. Do you believe in love at first sight?
  47. What sexual experience would be ideal for you?
  48. What’s the sweetest thing someone has ever done for you?
  49. Let’s play 20 questions – you ask one, then I’ll ask one.
  50. If you could go back in time and give yourself one piece of dating advice, what would it be?

Questions To Ask Your Boyfriend That Are Cute And Flirty

  1. Do you mind if I use your shirt as a pillow?
  2. How do you always look so great?
  3. What was the best text message you’ve ever received from me?
  4. Do you think I’m cute?
  5. What three things would you bring if we were stranded on an island together?
  6. How often do you think about me when we’re apart?
  7. Is there something on your mind that you’ve always wanted to ask me but haven’t yet?
  8. Do you mind if I hold your hand right now?
  9. Where would you take me if you could choose anywhere in the world to explore?
  10. What was our deepest conversation ever?
  11. Do you have any great flirting tips for me?
  12. What’s your favorite thing about me?
  13. What would you wish I knew more about you?
  14. Could you show me how to be an amazing kisser?
  15. What activity would you suggest we try together?
  16. Do you enjoy it when I show affectionate affection towards you in public?
  17. Could you teach me how to cook your favorite meal?
  18. What’s the craziest thing you’ve ever done for love?
  19. What have you always wanted to try in the bedroom?
  20. Do these questions bother you?
  21. Describe the moment when you knew you were in love with me?
  22. What’s your favorite memory of us together?
  23. Would you rather keep quiet or teach me how to play your favorite video game?
  24. What would make for the perfect date night for both of us?
  25. Do you mind if I keep a secret from you?
  26. What would your superpower be, if any?
  27. How does it feel when you’re with me?
  28. What has been the most romantic thing you’ve ever done for someone else?
  29. Do you have any flirting advice that I may not have heard before?
  30. What surprises you most about me?
  31. What could you sum up our relationship in three words?
  32. Demonstrate something that you’re particularly adept at doing for me.
  33. What’s your biggest turn-on?
  34. What do you enjoy most about cuddling with me?
  35. Who do you wish would join us on our date if there was one celebrity you could invite?
  36. Can you share with me a recent dream you had?
  37. What’s something that makes you wish for more time with me?
  38. How do you feel when I smile at you?
  39. What’s the most embarrassing thing that’s ever happened to you on a date?
  40. Can you give me some tips for dealing with challenging situations at work/school?
  41. What’s your favorite thing about me physically?
  42. What would it be if we could choose any activity together right now?
  43. How does it feel knowing I’m thinking of you?
  44. Share something unique that only you know about you.
  45. What keeps bringing back memories of me?
  46. Could you teach me how to dance along to your favorite song?
  47. What do you find challenging about asking these questions?
  48. Are there any topics that make you nervous?
  49. How would you describe your relationship with me in one sentence?

Flirty Questions To Ask A Guy To Know A Guy Deeper

  1. What is your biggest turn-on?
  2. What qualities do you look for in a girlfriend?
  3. Have you ever been in love before?
  4. What would be an ideal date?
  5. What is the sexiest thing a girl can do to turn you on?
  6. What romantic gesture have you ever performed for someone?
  7. How do you like to be touched?
  8. What adventurous act have you ever performed in the bedroom?
  9. What is your wildest sexual fantasy?
  10. What do you consider an essential aspect of any relationship to you?
  11. Have your feelings ever been hurt in public?
  12. Which part of a woman’s body do you find most beautiful?
  13. Where would you want to go on an ideal romantic getaway, and how do you like being pursued?
  14. What is your biggest fear when it comes to relationships?
  15. Have you ever had a one-night stand?
  16. What was the best compliment you ever received from a girl?
  17. How would you describe an ideal kiss to someone special?
  18. What is the most embarrassing thing that has ever happened to you on a date?
  19. What do you enjoy doing in your free moments?
  20. What would be your dream job if it existed?
  21. Do you feel comfortable taking risks?
  22. And finally, what’s your favorite pastime while lying in bed?
  23. What is the most important lesson you have learned from a past relationship?
  24. Do you believe in love at first sight?
  25. What would make for the perfect relationship for you?
  26. What has been the best thing that any woman has ever done for you?
  27. Do you believe in fate?
  28. What’s an ideal morning for you?
  29. How do you feel about being friends with an ex?
  30. What is your biggest goal in life?
  31. What is the most romantic thing you have ever said to someone?
  32. What is currently important in your life?
  33. How important communication in a relationship is?
  34. What has been your most adventurous act?
  35. What is the most valuable lesson you have learned in life?
  36. How do you feel about commitment?
  37. What’s an ideal wedding day?
  38. What’s your ideal self-image?
  39. What do you find most admirable about yourself?
  40. How would you prefer being approached by a girl?
  41. What is the most romantic thing a girl has ever said to you?
  42. What would you consider an ideal evening for you?
  43. What do you like doing to unwind after a long day?
  44. What activity do you like doing on weekends?
  45. How do you feel about being vulnerable in a relationship?
  46. What would be the perfect proposal to you?
  47. What’s your favorite way of showing affection?
  48. What qualities are most important when searching for the right partner?
  49. What is the most essential act you have ever performed for someone you cherish?

Flirty Questions To Ask A Guy You Just Met

  1. What do you like to do for fun? (Hopefully it includes me!)
  2. What kind of music do you enjoy listening to? (I’m curious if we share the same taste in music!)
  3. Where was the last concert you attended? (Maybe next time we should go together?)
  4. Do you enjoy dancing? (I’d love to dance with you)
  5. What’s your favorite drink? (I want to make sure I have everything you enjoy when we meet)
  6. On a first date, what would you like to do that involves getting to know me better?)
  7. Do you believe in love at first sight? (I believe that was just my experience!)
  8. What would make the ideal date for both of us? Do you enjoy cooking? (I hope that involves us being together!)
  9. What’s your favorite type of food? (Hopefully, I can impress you with it)
  10. What book do you enjoy reading most? We could read it together and have a lively conversation afterward)
  11. Do you enjoy traveling? (Let’s explore the world together)
  12. Where’s the coolest place you’ve ever been? (I want to go there with you!)
  13. Do you own any pets? (If we share an affinity for animals)
  14. What’s your favorite TV show? (Maybe we should binge-watch it together!)
  15. Do you have any siblings? (Hopefully, they aren’t as cute as you!)
  16. What’s your favorite hobby? (I would love to join in!)
  17. Do you enjoy exercising? (I want to be your gym buddy!)
  18. What’s your favorite sport? Maybe we should play it together!)
  19. Do you possess any hidden talents? (I can’t wait to find out!)
  20. What has been your craziest adventure yet? (I hope to be a part of it!)
  21. What was the best prank you ever pulled on someone else (hopefully not me!)
  22. And most importantly: what’s your biggest fear? With any luck, I hope I can help conquer it!)
  23. Do you prefer going out or staying in? (We should do both together!)
  24. What would make for the ideal weekend with me?
  25. Do you have any bucket lists? (Hopefully, mine includes spending time with you!)?
  26. What’s the most spontaneous thing you’ve ever done? (I hope it’s enough to ask me out on a date)
  27. Do you enjoy shopping? (I want to go shopping with you!)
  28. What’s your favorite type of movie? (Hopefully something we can watch together)?
  29. Do you believe in destiny? (I’m hoping it was destiny that brought us together!)
  30. What’s your favorite pastime when not working? (Hopefully, it involves me!)
  31. What has been the most romantic thing someone has ever done for you? (I hope I can top it)
  32. Do you enjoy surprises? (I have something special planned))
  33. What’s your favorite season? (I hope it’s the season of love)
  34. Do you have any nicknames? (Can I give one?)
  35. What would be your dream job, if it existed?
  36. What’s the craziest thing you’ve ever eaten? (Maybe we should try it together!)
  37. Do you like to party? (I would love to join in!)
  38. And lastly, do you enjoy taking care of business? Do we get along well?)
  39. What’s your favorite thing about yourself? (Hopefully, it’s your charming smile)
  40. Do you have a go-to pick-up line? (Hoping you’ll use it on me)
  41. What’s the sweetest thing anyone has ever said to you? (I’m hoping for something even sweeter!)
  42. Do you enjoy singing? (Maybe we should do an encore together!)
  43. What’s your favorite dessert? (I want to make it for you!)
  44. What would make the perfect day for you, if it involved spending time with me?)
  45. Do you have any tattoos? Show them off!
  46. And finally, what color do you love the most? (I wish to wear it!)
  47. Do you enjoy taking pictures? (I think we should take some cute selfies together!)
  48. What’s your favorite type of flower? (Let me know and i’ll surprise you with it)
  49. Do you enjoy cuddling? (I wish to cuddle with you too!)
  50. What has been your most daring act? (I hope to join you on your next expedition!)