213 Cute Questions To Ask Your Boyfriend That He’ll Love Answering

When you’ve been with a guy for a long time, you might think you know everything about each other. And sure, you probably do know a fair bit. However, that doesn’t mean your conversations need to get boring or that you should stop asking him questions. Here are some cute questions to ask your boyfriend when you’re bored and want to peek into his mind.

  1. “How would you describe me in three words?” It’s always interesting to know the qualities you have that stand out most to other people. Hearing what your boyfriend thinks will certainly warm your heart. Think about what three words you associate with him too!
  2. “What do you think makes our relationship work so well?” You’re together for a reason, so why is that? You probably have a ton of chemistry and get on well, but what’s the real secret to your happiness as a couple? See if his answer matches yours and discuss!
  3. “What are your favorite memories from our relationship?” If you’ve been together a while, there are probably tons. Reminiscing about some of your best times is a fun way to keep your connection strong.
  4. “What’s your favorite kind of date to go on with me?” This is one of those cute questions to ask your boyfriend that also serves a purpose. You can take his response and use it to plan an amazingly fun and romantic date with him. Score!
  5. “If money wasn’t an object, what kind of gifts would we get each other?” It’s always enjoyable to ask these kinds of hypothetical questions. It’s fun to fantasize about what you’d do if you had endless cash at your disposal.
  6. “What’s the most romantic thing I could ever do for you?” If you’ve done it already, pat yourself on the back! If it’s something you haven’t done but is feasible, you’ve just been handed some pretty great inspiration.
  7. “If I was going to cook you an extravagant meal, what would I make?” If you’re a great cook and someone who likes spending time in the kitchen, use your skills to endear yourself to him even more. Just make sure he takes care of doing the dishes!
  8. “What makes you feel closest to me?” Hopefully, you have a deep, unbreakable bond. But how did you get there? What is it that keeps you so close? Asking this question will give you the answer. Do you agree?
  9. “What’s the best compliment I’ve ever given you?” Women aren’t the only ones who love compliments — men like compliments too. What ego boost have you given him that he loved? What made him feel great about himself? Take note and mention it more often!
  10. “What made you attracted to me?” Yes, this is a little self-serving, but it’s still a cute question to ask your boyfriend. Just be sure you can answer the same question. It’s only fair!
  11. “How early did you know that you wanted to be with me long-term?” He might have known he was into you, but when did he know it wasn’t just physical attraction and there was something deeper there?
  12. “Did you ever worry that I wasn’t as into you as you were into me?” Hopefully not, because that’s never a good feeling.  Women worry so much about whether we’re imagining our partners’ attraction, so it’s comforting to know guys go through the same things.
  13. “What songs remind you of me/our relationship?” Do you have music that defines your relationship? What is it? You might know some of the songs, but he probably has others. Ask your boyfriend cute questions like this to warm your heart.
  14. “What’s your favorite piece of clothing that I own?” Maybe you’ll wear it more often if he’s lucky.
  15. “What’s your definition of a healthy relationship?” You should probably know this already, but it’s always nice to get a reminder. Everyone values different qualities in a relationship, but knowing what he thinks is eye-opening.
  16. “Where would you go on your honeymoon if you could go anywhere in the world?” This is one of the cute questions to ask your boyfriend because it hints at long-term love. You’re not asking him to propose just yet, but it’s fun to put the idea in his head.
  17. “Do you believe in soulmates? Why or why not?” This could cause a fight if you don’t get the answer you want. However, assuming you know him well enough, this is probably a pretty safe question to ask. If anything, it will spawn a good discussion.
  18. “What’s the pet name you most like to be called?” You probably have your fair share of nicknames for your boyfriend already. Honey, baby, sweetheart. What one does he like the most? Maybe there’s a new name you could start calling him to show your endearment.
  19. “What do you miss most about me when we’re away from each other?” Absence does make the heart grow fonder and it’s good to miss each other. However, when you’re not together, what are the specific things he misses most about you? What do you miss about him?
  20. “What’s a quality I bring out of you that no one else does?” You’re his girlfriend. You have a special bond that’s different from any that he shares with someone else. What side of his personality do you pull from him that no one else gets to see?
  21. “What’s your favorite inside joke that we share?” You probably have a list as long as your arm, but what’s his favorite one?

More cute questions to ask your boyfriend

  1. “If we were characters in a Disney movie, who would we be?”
  2. “What’s your favorite memory of us together?”
  3. “If you could describe our relationship using a song, which one would it be?”
  4. “How do you imagine our future together?”
  5. “What was the exact moment you realized you liked/loved me?”
  6. “If we were animals, what would we be and why?”
  7. “What’s your favorite thing about our dates?”
  8. “If we could travel anywhere together, where would you want to go?”
  9. “Do you remember what you were thinking the first time we held hands?”
  10. “If we opened a cafe together, what would it be called?”
  11. “What was the silliest reason you’ve ever smiled because of me?”
  12. “What’s your favorite thing I wear?”
  13. “If our lives were a board game, which one would it be?”
  14. “How would you describe our relationship to aliens?”
  15. “What do you love most about our adventures together?”
  16. “Which of my quirks do you find the most endearing?”
  17. “If we were a superhero duo, what would our powers be?”
  18. “What’s the sweetest dream you’ve ever had about us?”
  19. “What’s your favorite scent on me?”
  20. “If our love story was a book, what would the title be?”
  21. “What’s the funniest thing I’ve said in my sleep, if you’ve heard me talk?”
  22. “How do you feel when you catch me looking at you?”
  23. “What movie couple do you think we’re most like?”
  24. “If we were stranded on an island, what three things would you want with us?”

Fun, random questions to ask your boyfriend

  1. “If you could be any fictional character for a day, who would you be?”
  2. “Would you rather fight one horse-sized duck or a hundred duck-sized horses?”
  3. “If you had a magic wand, what’s the first thing you’d do with it?”
  4. “Which wild animal would you want as a pet?”
  5. “What’s the weirdest food you’ve ever tried and liked?”
  6. “Would you rather travel to the future or the past?”
  7. “If you were to join a circus, what act would you perform?”
  8. “If your life was a video game, what would it be called?”
  9. “Would you rather have the ability to talk to animals or speak every language fluently?”
  10. “If you could swap lives with a historical figure for a day, who would it be?”
  11. “What’s the most hilarious animal video you’ve ever seen?”
  12. “Which planet in our solar system would you most like to visit?”
  13. “If you could be on the cover of any magazine, which one would it be?”
  14. “What movie title best describes your life?”
  15. “What’s your spirit vegetable?”
  16. “If you could be any kitchen appliance, which one would you be and why?”
  17. “If you were a ghost, where would you haunt?”
  18. “If you had to eat only one dessert for the rest of your life, what would it be?”
  19. “Would you rather be able to teleport anywhere or read minds?”
  20. “Which fictional world would you love to live in?”
  21. “If you could have a theme song that played every time you entered a room, what would it be?”
  22. “What’s the strangest dream you can remember?”

Romantic questions to ask your boyfriend

  1. “What was the first thing you noticed about me?”
  2. “What’s your favorite memory of us together?”
  3. “How do you know when you’re truly in love with someone?”
  4. “How do you feel when we’re apart?”
  5. “What is the most special moment we’ve shared, in your opinion?”
  6. “What made you realize you wanted to be with me?”
  7. “What are the little things I do that make you feel loved?”
  8. “What’s your favorite thing about waking up next to me?”
  9. “How do you picture our life 10 years from now?”
  10. “What song reminds you of our relationship?”
  11. “What do you think is the key to a successful relationship?”
  12. “How have I changed your life since we met?”
  13. “Where is the most romantic place you’d like to take me?”
  14. “When did you first know you loved me?”
  15. “What makes our relationship unique to you?”
  16. “What’s the most romantic date you can imagine?”
  17. “How do you feel when you read my messages or hear my voice?”
  18. “What are your dreams for our future together?”
  19. “What do you think is the most important aspect of a romantic relationship?”
  20. “How do you handle the moments when you’re upset or angry with me?”
  21. “Is there a quote or poem that reminds you of us?”
  22. “How do you think we’ve grown as a couple since we first met?”
  23. “How would you describe the way we complement each other?”

Silly questions to ask your boyfriend

  1. “If you were a vegetable, which one would you be and why?”
  2. “Would you rather have fingers as long as your legs or legs as long as your fingers?”
  3. “What would you do if you woke up and you were the size of a LEGO man?”
  4. “If you could only eat one color of food for the rest of your life, what color would it be?”
  5. “If you had to replace your hands with objects already in your house, what would they be?”
  6. “What animal noise do you think you can do the best?”
  7. “If our lives were a sitcom, what would the title be?”
  8. “If you were a superhero with a useless power, what would that power be?”
  9. “Would you rather sneeze out confetti or fart out glitter?”
  10. “If you could choose, what would your entrance theme song be every time you walked into a room?”
  11. “If you were a scent, what would you smell like?”
  12. “Would you rather have a permanent clown nose or permanent clown shoes?”
  13. “If you could talk to one species of animal, which one would you pick?”
  14. “What’s the funniest name you can think of for a pet rock?”
  15. “If you had to give up one of your five senses, but you got to choose an animal’s sense to replace it, what would you pick?”
  16. “Would you rather wear socks on your hands or gloves on your feet for a day?”
  17. “If you had to use a fake name for the rest of your life, what would it be?”
  18. “What’s the weirdest combination of foods you’ve ever eaten and enjoyed?”
  19. “If you could only dance one dance move for the rest of your life, what would it be?”
  20. “Would you rather have spaghetti for hair or sweat maple syrup?”
  21. “If you were trapped in a cartoon universe for a month, which one would you choose?”
  22. “If you could replace all the water in one ocean with something else, what would it be?”

Flirty questions to ask your boyfriend

  1. “If you could sum up our chemistry in one word, what would it be?”
  2. “What did you think when you first saw me?”
  3. “What’s the most romantic scene from a movie you’d like to recreate with me?”
  4. “How do you feel when other guys look at me?”
  5. “What’s your favorite outfit of mine?”
  6. “Do you ever dream about me?”
  7. “Where’s the most adventurous place you’d like to kiss me?”
  8. “What’s your biggest turn-on?”
  9. “What’s your favorite feature of mine?”
  10. “How would you react if I whispered something naughty into your ear right now?”
  11. “Do you prefer cuddling or making out?”
  12. “What was your first impression of me? Has it changed?”
  13. “Have you ever had a dream about me that you’re too shy to tell me?”
  14. “How would you describe our first kiss?”
  15. “What do you find most tempting about me?”
  16. “If I looked in your recent search history, would I find anything surprising about me?”
  17. “How would you react if I wore that dress you love tonight?”
  18. “Where’s the most exciting place you’ve ever done it?”
  19. “What do you think about when you’re lying in bed alone?”
  20. “Have you ever played truth or dare? Want to try with me?”
  21. “What’s the one thing about me that drives you nuts (in a good way)?”
  22. “If you could only touch or kiss me for the rest of your life, which one would you choose?”
  23. “Do you have a secret fantasy?”
  24. “How do you imagine our next date?”
  25. “What’s the most risqué text you’ve ever sent or received?”
  26. “If we had the whole day to ourselves, with no interruptions, what would you want to do?”

Personal questions to ask your boyfriend

  1. “What’s a childhood memory that shaped who you are today?”
  2. “Is there something you’ve never told anyone because you were too scared of how they’d react?”
  3. “How do you handle stress or difficult situations?”
  4. “Who in your life has influenced you the most?”
  5. “What’s your biggest regret?”
  6. “What are your views on spirituality or religion?”
  7. “How do you define success in life?”
  8. “What are your greatest fears about our relationship?”
  9. “Is there something from your past that you find hard to move on from?”
  10. “How do you want to be remembered?”
  11. “What’s your stance on forgiveness? Is there something you find hard to forgive?”
  12. “Which family member are you closest to and why?”
  13. “What’s something you’re really proud of but never get an opportunity to talk about?”
  14. “How do you deal with failures or setbacks?”
  15. “What’s the most challenging experience you’ve been through?”
  16. “What are your long-term goals?”
  17. “What’s your biggest insecurity?”
  18. “What values are most important to you in a relationship?”
  19. “How do you feel about sharing your passwords with a partner?”
  20. “Is there a dream or ambition you’ve never shared with anyone?”
  21. “How do you handle disagreements in a relationship?”
  22. “What does vulnerability mean to you? When was the last time you felt truly vulnerable?”
  23. “What’s a lesson you’ve learned from a past relationship?”
  24. “How has your upbringing influenced the person you are today?”
  25. “What’s a belief you held strongly in the past that you no longer believe in?”
  26. “How do you handle it when your beliefs and values are challenged?”
  27. “What event in your life would you say has had the most impact on you?”
  28. “How do you handle jealousy or insecurity in a relationship?”
  29. “Is there a book or movie that changed your perspective on life?”
  30. “What does a perfect day look like for you?”
  31. “How do you prioritize your relationships, career, and personal growth?”
  32. “What’s a trait or habit you’d like to improve about yourself?”
  33. “Do you have a ritual or routine that’s sacred to you?”
  34. “What’s your most treasured memory?”
  35. “How do you express love and how do you like to receive it?”
  36. “What’s the most difficult challenge you’ve overcome?”
  37. “Do you have any unresolved issues or conflicts with family members?”
  38. “How do you cope with loss or grief?”
  39. “What’s something you’ve always wanted to learn or master?”
  40. “How do you feel about the concept of fate or destiny?”
  41. “What’s your philosophy on money and wealth?”
  42. “Is there something you’re hesitant to tell me?”
  43. “How do you handle criticism, both constructive and negative?”
  44. “Have you ever experienced a crisis of identity or self-worth?”
  45. “What does ‘home’ mean to you?”
  46. “How do you envision your life in retirement?”
  47. “What role does tradition play in your life?”
  48. “Do you believe in second chances? Why or why not?”
  49. “What are your thoughts on vulnerability and openness in a relationship?”
  50. “If you could go back and give your teenage self advice, what would it be?”

Sweet questions to ask your boyfriend

  1. “What makes you feel most loved and appreciated?”
  2. “How can I best support you when you’re going through a tough time?”
  3. “What’s a dream or goal of yours that you’d love for us to achieve together?”
  4. “Do you have a favorite memory of us that always makes you smile?”
  5. “How can I make every day special for you?”
  6. “What little things do I do that mean the most to you?”
  7. “Is there a song or movie that reminds you of our relationship?”
  8. “What’s your favorite thing about our relationship?”
  9. “How do you envision us growing old together?”
  10. “What’s something you’ve always wanted to tell me but haven’t had the chance to?”
  11. “How do you feel when we’re apart from each other?”
  12. “What’s a tradition or routine we have that you cherish the most?”
  13. “What do you love most about our mornings or nights together?”
  14. “Is there a place you’d love for us to visit together?”
  15. “What’s the best surprise you’ve ever received from me?”
  16. “How has our relationship changed you as a person?”
  17. “What’s your favorite way to spend a rainy day with me?”
  18. “What words come to your mind when you think of our love?”
  19. “How do you hope our relationship inspires others?”
  20. “What’s a quality of mine that you’ve come to adore?”
  21. “How do you feel when you read messages from me?”
  22. “Is there a scent or aroma that reminds you of a moment with me?”
  23. “What do you look forward to the most about our future together?”
  24. “What’s the best piece of advice about love you’ve ever received?”
  25. “How do you feel when you think about our first date?”
Jennifer Still is a writer and editor with more than 10 years of experience. The managing editor of Bolde, she has bylines in Vanity Fair, Business Insider, The New York Times, Glamour, Bon Appetit, and many more. You can follow her on Twitter @jenniferlstill