Flirty Questions to Ask a Guy/Boyfriend

160 + Deep Flirty Questions to Ask a Guy you Like (He’ll Love These)

Flirting is an art that needs to be mastered. It’s not hard, but you have the right moves for it! Picture this: You’re out at a bar and see somebody handsome coming over your way – immediate freeze frame before they can even say hello.

But we’re here with some examples on how to do it right with a list of flirty questions to ask a guy when you go on a hot date or just texting a person you meet on an online dating app. 

Naughty & Funny Questions to Ask a Guy/Boyfriend


Flirty questions can be a great way to get to know someone better, and they can also help you determine if someone is interested in you. So don’t worry about being awkward anymore because techniques work wonders!! Ready? Let’s dive in.

21 Questions To Ask a Guy to Break The Ice

Here are 21 questions to ask a guy you’re meeting for the first time to break the ice and get along well!

  1.  What’s the funniest thing that has happened to you recently? 
  2. What are you passionate about? 
  3. What would you do with a kiosk in your bedroom where you could order anything you want for delivery to your room without even having to speak?
  4. What career would you choose if you could have any? 
  5. What’s your favorite game to play?
  6. Which is your goal in your life?
  7. What type of workouts do you enjoy?
  8. Do you workout?
  9. Who is the person you feel most at ease with?
  10. What are you most nervous or afraid about?
  11. Do you consider yourself as a romantic guy?
  12. What’s the most mortifying thing that’s ever happened to you?
  13. What’s the one thing that makes you proud of yourself?
  14. If you could transform into any animal, which would it be?
  15. Truth or dare?
  16. Who is your favorite actress?
  17. What’s your idea of the perfect date? 
  18. What’s the craziest thing you’ve ever done? 
  19. What were you like in school?
  20. What’s the craziest thing you’ve ever done?
  21. Do you have any insecurities?

Flirty questions to ask a guy.

Whether you’re meeting the guy for the first time or 3rd time, these questions work like a charm and make you irresistible!

Flirty Questions to Ask a Guy/Boyfriend

  1. What are your thoughts on long-term relationships? 
  2. What’s your biggest fear in a relationship? 
  3. How do you think we’re going to be together? 
  4. What is the most romantic thing your partner has ever done for you?
  5. What do you notice first in a woman?
  6. Are you an extrovert or an introvert?
  7. What do you think about my outfit?
  8. What are your thoughts on love at first sight?
  9. Which place would you take a woman if you had the power to do so?
  10. How is someone like you single?
  11. How do you know if someone is the right person for you?
  12. How do you know if a woman is perfect for you?
  13. What’s your turn-on?
  14. How are you still single?
  15. What is the worst date you’ve ever been on?
  16. Do you prefer when a woman makes the first move?
  17. What’s your biggest turn-off? 
  18. What type of person do you like to be with when you’re out on a date? 
  19. Name three things that you can’t live without.
  20. What kind of things make you feel alive?
  21. Do you like adventure or staying in more?
  22. What kind of trouble did you used to get into when you were younger?
  23. Are you more spontaneous or more planned out?
  24. How can I make a guy fall for me?
  25. How do you like being treated when you’re flirty with someone?
  26. Do you like to be daring or play it safe?
  27. What’s the most effective pickup line you’ve ever heard?
  28. Do you have any secret fantasies?
  29. Do you like bars or pubs?
  30. What is your idea of the best romantic date?
  31. What would you do to seduce me?
  32. Have you tried having a one-night stand?
  33. What do you think is your best feature?
  34. Do you like it when a woman flirts with you?
  35. What would you do if your girlfriend smiled at a strange guy?
  36. Do you like cuddling?
  37. What makes you really uncomfortable?
  38. Do you like public displays of affection?
  39. Would you prefer to spend your evening viewing the sunset or going to a movie?
  40. Does your weekend plan include me?
  41. Are you a Netflix kind of guy?
  42. What is your favorite thing to do on a date?
  43. Will you be able to change your religion just to be with someone?
  44. Would you move to another country just to be with someone?
  45. What is your favorite superpower?
  46. Would you like to go on a local trip or explore outside the country?

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Love Questions

Love is a feeling that cannot be described in words. It’s something that you feel deep inside your heart. If you’re looking to get to know someone deeper, you need to ask them the right questions. Here are some love questions to ask a boy:

  1. Do you believe that love is essential in a relationship? 
  2. What are your thoughts on marriage? 
  3. Do you believe in soulmates? 
  4. What is the most romantic and cute thing someone has ever done for you?
  5. How would you describe love in your own words? 
  6. What’s the best feeling in the world or worst? 
  7. When was the last time you felt truly in love? 
  8. What’s your favorite love song or movie? 
  9. Do you think love conquers all? 
  10. What are your thoughts on fate and destiny? 
  11. Do you believe that everyone has a soulmate? 
  12. What’s the best way to show someone you love them? 
  13. How do you think love changes people? 
  14. What’s the worst thing that can happen in a relationship? 
  15. Do you think love is worth all the drama? 
  16. What are your thoughts on online dating?
  17. What are your thoughts on long-distance relationships? 
  18. How would you describe the perfect relationship? 

Fun & Random Questions to Ask a Guy

  1. What is your favorite comic book? 
  2. What would be your dream vacation spot? 
  3. Who is your favorite musician or band? -What is your favorite sports team? 
  4. What is your favorite TV show? 
  5. What is your favorite movie? 
  6. What is your favorite book? 
  7. What is your favorite food? 
  8. What is your favorite hobby? 
  9. What do you like to for fun? 
  10. What is your favorite animal? 
  11. What is your favorite color? 
  12. What is your favorite season?
  13. What are your hobbies outside of work or school? 
  14. Do you have any pets? 
  15. Do you prefer city life or country living? 
  16. Coke or Pepsi? McDonald’s or Burger King? iPhones or Android phones? 
  17. Do you smoke?
  18. Would you ever go to a nude beach?
  19. What excites you in life?
  20. If you won the $100000, how would you like to spend your money?
  21. What is the worst pick up line you ever used and failed?
  22. Would you cook for your date?
  23. What personality trait in a woman keeps you obsessed?
  24. Would you ever forgive your partner if they cheated on you or betrayed you?
  25. What do you think women want the most?
  26. Are you still friends with your ex’s?
  27. Would you rather go skiing or watch a movie?
  28. What would you choose between money and love?
  29. Are you, by chance, ticklish?
  30. Would you choose career or love?
  31. What emoji do you frequently use while texting?
  32. Would you rather stay in or go out?
  33. Are you into beauty or brains?
  34. What is your happy place?
  35. Do you like surprises?
  36. Do you want to be famous?
  37. Tell me about the craziest date you’ve ever been on.
  38. What is a perfect day for you?
  39. What’s your “type”?
  40. What’s your greatest skill?
  41. I like your perfume! What are you wearing?
  42. What do you like about me?
  43. When did you know you liked me?
  44. What puts you in a good mood?
  45. How would your friends describe you?
  46. Do you have a bucket list?
  47. Which 2 words would you use to describe yourself?
  48. What is that one food you cannot imagine living without?
  49. Are you a foodie?
  50. What’s your guilty pleasure in life?
  51. Are you an adventure-loving person?
  52. If you could time travel, to which year would you go back?
  53. What’s your first impression of me?
  54. When was the last time you cried?
  55. Do you think one should be friends first before getting into a relationship?
  56. Describe your life in 3 words.
  57. What is the best compliment you’ve ever received?
  58. Have you ever dated any of your friends?
  59. What’s your pet peeve?
  60. What do you dislike in a girl?
  61. Who’s your favorite avenger?
  62. Avenger or DC?
  63. What’s your nickname?
  64. Are you good boyfriend material?
  65. Have you ever had a crush on your teacher or professor?
  66. Are you into sweets or savory food?
  67. What’s the one thing you would absolutely do before you die?
  68. Dogs or cats?
  69. Do you prefer spicy food?
  70. What’s your favorite movie dialogue?
  71. Do you believe in ghosts?
  72. Ice cream or chocolate?
  73. What’s your dream vacation?
  74. How will you make me fall for you?
  75. Do you have any tricks up your sleeve to make me fall for you?
  76. What’s your favorite ice cream flavor?
  77. Do you believe in soulmates?
  78. Do you get shy around me?
  79. Which food do you dislike the most?
  80. What’s your dream job?
  81. What do you do for entertainment?
  82. Do you have a favorite love song?

All in All

With these deep questions, the guy you’re interested in will be blown away by how interested you are in talking with. Also, with the bank of these flirty questions to ask a guy, you will better understand what kind of a person he is! So do you have any more questions to add to these lists? We are game! Comment your thoughts below!


1. How do you flirt with a guy over text?

  • Start with a simple compliment. For example, “I like your sense of humor” or “You’re really smart.”
  • Send a flirty picture. A picture of you looking happy is sure to get his attention!
  • Make a bold move. If the conversation is going well, suggest meeting up for coffee or drinks. He won’t be able to resist.

2. How do you make a guy blush?

Here are are a few ways to make a guy blush: 

  • Compliment them on something unique about them that you appreciate. This could be anything from their smile to their sense of humor. If you know they are working hard on something, tell them how proud you are of their dedication.
  • Focus on physical contact. A gentle touch on the arm or hand can do wonders, especially if you hold eye contact. You could also try giving them a hug or kiss on the cheek (assuming you know them well enough.)
  • Bring up some happy memories between the two of you. Take a walk down memory lane and recount some of your favorite moments together – this is sure to bring a smile.

3. How do you make a guy smile?

Some general tips that might help include:

  • Making him feel appreciated.
  • Being genuine and authentic.
  • Being friendly and chatty.
  • Being flirty and playful.

Ultimately, the key is to be yourself and to find out what he enjoys most so you can put a smile on his face. 

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