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205 Cutest Questions To Ask Your Boyfriend

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Every relationship goes through different phases, from the initial phase when the partners get to know each other, to the advanced phases when they get to define the relationship, their expectations, and what they want from the relationship. Through all these stages, asking questions remains one of the best ways partners in a relationship achieve all these.

When doubt arises about the commitment of the partner(s) to the relationship, or when the lovey-dovey vibes are beginning to go down, asking questions is in fact one way to clearly understand what is going on. But even more to that, asking certain questions can also help add some new spice to the relationship. These questions can stimulate your boyfriend to love you even more and to give you responses that would spark your love fire.

Here in this post, you are going to find an exhaustive list of the cutest questions to ask your boyfriend. For these to work effectively, I recommend that you go through them regularly without making efforts to memorize them. That way they become a part of you and you find yourself asking these questions in the middle of your conversations.

65 Cutest Questions to Ask your Boyfriend

These questions here are some of the cutest questions you can ask your boyfriend. They are cute because your boyfriend is not going to give you a "yes" or "no" response but what he would say or do might make you feel more loved.

  1. In less than eight words, how much do you love me?
  2. How long do you want to spend with me?
  3. If you could describe me with three words, what would they be?
  4. Is there anything you dislike about me?
  5. Have you ever dreamt about me?
  6. How many hours of the day do you think about me?
  7. Does it make you smile when I send you a text message?
  8. Do you think about me during the day?
  9. What reminds you of me?
  10. What kind of movie do you like us to watch together?
  11. Do you think someone can be too much in love?
  12. What was your first impression of me?
  13. If I was really sad, what would you do to cheer me up?
  14. Do I make you want a future with me?
  15. If I was scared, would you hold me?
  16. Would you ever take me out on a picnic under the stars?

  17. What is your favorite pet name for me?
  18. What is a quirky thing about me that you love?
  19. Do you get butterflies when you read my notes?
  20. If I looked completely different, would you still love me?
  21. Do you think I’m cute?
  22. Do I look cute while working out?
  23. If I was a dessert, what would I be and why?
  24. How would you describe the way I smell?
  25. What did you think of yourself after our first fight?
  26. What kind of future do you see between the two of us?
  27. Do you like to hold my hand?
  28. Do you feel warm when we hug?
  29. Do you like the way I walk?
  30. Would you ever write a song for me?
  31. Have you ever had a dream about me?
  32. Would you risk your life to save mine?
  33. Do you think I’m pretty?
  34. Would you take my hand to dance, even if nobody was on the dance floor?
  35. Fun questions to ask your boyfriend
  36. What’s the funniest thing that someone has drunkenly confessed to you?
  37. How often do you go into a room and forget why you went into the room?
  38. How often is your brain on autopilot?
  39. What names were ruined for you because you knew someone terrible with that name?
  40. What’s the most stress-relieving thing you can get/do for less than 20$?

  41. What’s the grossest thing you’ve drunk?
  42. What’s your favorite waste of time?
  43. Where is the craziest place you have danced?
  44. What silly thing do you take a lot of pride in?
  45. If animals were as intelligent as humans, what types of jobs would certain animals be uniquely qualified for?
  46. Do fish have necks?
  47. What’s the weirdest celebrity crush you’ve ever had?
  48. If you were a vegetable, what vegetable would you be and why?
  49. What’s the weirdest conversation you’ve ever overheard?
  50. What would your dream mansion look like?
  51. What would you do if a guy asked for your number?
  52. What kind of ice cream describes you best?
  53. If you owned a boat, what would you call it?
  54. What’s the story behind your last Instagram photo?
  55. What’s the worst first date you’ve ever had?
  56. If you could choose a superpower, what would you choose?
  57. What crazy things will you do if you ever become rich?
  58. What’s the last thing you Googled?
  59. What’s the weirdest wrong number text or phone call you’ve gotten?
  60. If you could change your first name, what would be the most epic name you could choose?
  61. What should be the next advancement in shoes?
  62. What would you do first if you gained the ability to fly?
  63. What is the coolest flag in use?
  64. If you had a secret lair like Batman or Superman, what would it be like?
  65. What incredible thing do you wish you could eat?

60 Romantic Questions to Ask your Boyfriend

The cute questions above are quite enough to re-kindle some love feelings between you both. However, if you want to step it up a little, here are some romantic questions you can also ask your boyfriend.

  1. Do you believe there is only one person you are meant to be with?
  2. If I were a fruit, what fruit would you call me?
  3. Do you miss me the way I do each night you are away?
  4. When can we just move in together already?
  5. Why do you always make my heart skip a beat?
  6. How was able to live without you before I met you?
  7. Can you show me how many times can you kiss me right now?
  8. Can you show me how long you can hug me?
  9. What is that one thing you can never do to me?
  10. What’s one difference between us that you absolutely love?
  11. What’s one similarity between us that you absolutely love?
  12. Is love something that scares you?
  13. What’s one thing you want to do together that we’ve never done before?
  14. Where is your favorite place to be with me?
  15. What song makes you think about me?
  16. Was it love at first sight with us?
  17. What’s a new nickname/pet name that you would like to call me?
  18. Which trait of mine drew you towards me?
  19. How did you feel when we had our first kiss?
  20. Do you prefer a good hug or a good kiss?
  21. If our relationship ended, what’s the one thing about it you’d miss the most?

  22. What’s one thing you feel our relationship is lacking?
  23. Do you think I’ve been vulnerable in our relationship?
  24. What’s one secret you have wanted to tell me, but haven’t?
  25. Do you think I’m the ‘right’ person for you? (If yes) What about me makes me the ‘right’ person?
  26. What do you think I’d say is your most attractive quality?
  27. What’s the most romantic movie you’ve ever seen?
  28. What is the number one best thing about our relationship?
  29. What’s your favorite way to receive affection?
  30. Do you want a big wedding or a small one?
  31. What’s your favorite way to show affection?
  32. What’s the sexiest dream you’ve ever had about us?
  33. Do you think you’ll ever want to settle down and have kids?
  34. If we could go anywhere together right now, where would you want to go?
  35. How do you think we both have changed since we first started dating?
  36. What about us is both exactly the same since we first started dating?
  37. What about us do you think works well together? How do we balance each other out?
  38. What does love mean to you?
  39. What do I mean to you?

  40. Flirty and dirty questions to ask your boyfriend
  41. What do you see when you close your eyes kissing me?
  42. Would you hold my hand in public?
  43. Where is your favorite place to be massaged?
  44. Would you kiss me on the neck?
  45. How many times did you want to kiss me before our actual first kiss?
  46. What part of my body do you like the most?
  47. Guess what part of your body I like the most.
  48. When was our most romantic kiss?
  49. Do you like to cuddle?
  50. Would you kiss me in public?
  51. Would you ever go skinny dipping with me?
  52. How would you describe the way I kiss?
  53. Would you rather hug for 5 seconds or kiss for 1 second?
  54. Do you like it when I touch your face?
  55. Would you ever take a bath with me?
  56. What is your favorite sexual feature of mine?
  57. What do you feel when you look into my eyes?
  58. What was your feeling when we had our first kiss?
  59. Where is your favorite place to be kissed?
  60. Would you kiss me on the wrist?

55 Personal Questions to Ask your Boyfriend

Just want to know your boyfriend better, want to know specific aspects about him? Here are some questions you should ask him.

  1. How many children do you plan to have?
  2. What is your preferred age to get married?
  3. Where do you see yourself in the next ten years?
  4. Who is the best girl you have ever or currently dating?
  5. What’s the worst dream you’ve ever had?
  6. What do you get overly emotional about?
  7. What event made you mature as a person the most?
  8. What’s one thing that you’ve never told anyone?
  9. What’s something you believe that most people don’t?
  10. Is there anything you’re afraid of in life?
  11. What’s your biggest regret?
  12. Who is your favorite family member?
  13. What’s the best way to earn somebody’s respect?
  14. What’s your best memory from growing up?
  15. What is your favorite thing to do in your spare time?
  16. Which of your friends do you like to spend time with the most?
  17. What was your favorite toy?
  18. What makes life worth living to you?
  19. What’s your favorite animal and why?
  20. If you had to leave your house, what is the one thing you would take with you?

  21. What tv show could you binge-watch all day?
  22. What’s the hardest truth you’ve come to grips with?
  23. What quirks does your body have?
  24. What music do you like that you wish you listened to more?
  25. How soft are you?
  26. What are you a snob about?
  27. What makes you the happiest?
  28. What would it look like if you fully lived up to your potential?
  29. How curious are you?
  30. How do you fight off procrastination?
  31. What’s your jam?
  32. How easily do you change your opinions?
  33. What makes you feel alive?
  34. What traits do you like about yourself?
  35. If you could change one thing about your life, what would it be?
  36. What is one thing that you wouldn’t change about your life?
  37. What’s your favorite drink and why?
  38. If you had to eat the same food for a month, what would it be?
  39. Where would you live if money and work were not a factor?
  40. Do you prefer to listen to your heart or brain when making important decisions?
  41. What would you do if money and work were not factors?
  42. Who is one person you wish you could be?
  43. Who is someone you looked up to as a kid?
  44. What’s the best piece of advice you ever received?
  45. What is your biggest pet peeve?
  46. If your life were a movie, what would it be called?
  47. What is one thing on your bucket list?
  48. Would you ever quit your job to travel the world?
  49. What are three words you would use to describe yourself?
  50. In what situations do you act least like yourself?
  51. What word describes you better than any other word?
  52. What are you really obsessed about?
  53. How often do you get into arguments with people on the internet?
  54. What do you want to get out of life?
  55. How adventurous are you?

25 Random Fun Questions to Ask your Boyfriend

These questions do not have any personal or romantic significance but they can help you understand the social aspect of your boyfriend, his hobbies, his friends, his preferences, etc.
  1. Hotdog or hamburger, which do you prefer?
  2. What is your most valuable possession?
  3. What is your favorite food?
  4. What is the last thing you would ever put in your mouth?
  5. Do you like travelling a lot?
  6. Ice cream or milkshake?
  7. What would the title of your autobiography be?
  8. You can only wear one thing for the rest of your life. What do you choose?
  9. If money were no object, what would you have for breakfast every day?
  10. If you could have dinner with three people in the world, who would they be?
  11. What’s a dirty habit that you can’t get rid of?
  12. What you rather eat McDonald’s or a nice, healthy meal?
  13. What’s the weirdest celebrity crush you’ve ever had?

  14. What would you do if we were in zero gravity?
  15. What’s the funniest screw-up you’ve ever seen on social media?
  16. If someone had something on their face, would you tell them?
  17. What’s the worst purchase you’ve ever made?
  18. What's your best purchase ever?
  19. Do you think I would look sexy with glasses?
  20. Who is your favorite cartoon character ever?
  21. If you could throw anything against a brick wall, what would it be?
  22. You just found five dollars on the ground. What do you do?
  23. Would you rather live in a cave or under the sea?
  24. If there was only one cookie left, would you give it to me?
  25. If you could feed me a dessert, what would you pick?

Why Do You Ask these Question?

Like I already mentioned earlier, there are several reasons why you want to ask your boyfriend any of these questions.
  • You may want to understand and know him better.
  • You may want to find answers to some deep
  • You may want to define the course of your relationship
  • To open up to you about some deep things about his life
  • You may want to establish your compatibility, or
  • To spark love feelings or experience a moment of romance


When you ask your boyfriend these questions, you not only get the above needs. Asking a guy questions establishes a sense of pride within him that will make him love you even more. It makes him feel that you depend on him for some answers. This makes every man feel like a hero, and as expected he will love you even more. This is called the Hero Instincts.

Also, asking your boyfriend these questions will give him the reassurance that you are willing to do all it takes to understand him, that you are willing to invest in getting to know him so that the relationship can work. This further strengthens his love for you.

Lastly, if you want your relationship with your boyfriend to last and blossom lovingly, you have to develop the habit of listening to him. There is nothing people hate other than being with someone who does not listen to them. As you ask questions, give him time to answer them. This sends a message to their brain each time you do so, that you are ready to listen to them. 

Love is sweet with the right person. If you have found yours now, hold them well and give them all that your love has to offer. But if you are still searching, you can apply the Hero Instinct to get your dream man's attention. Read here if you are tired of being single. Celebrate love, it's worth it!

Prosper Yole

I am a lifestyle blogger, I write useful articles on successful life tips and hacks. Posts bearing Prosper Yole as author are either written by the blog author himself or by our various other contributors. Thank you for reading through. I look forward to having you more often. Please subscribe to my blog and follow me on Twitter @ProsperYoleOfficial


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