In order for a relationship to last long-term, you need to be on the same page with your loved one. There will be no “connection” if you are not on the same wavelength. You can know how your boyfriend feels and thinks through a sensible conversation.

But, guys are known to be a little bit closed off when it comes to talking. A lot of them even use one-word answers. Sometimes, it really feels like pulling their teeth before we can get them to talk.

You need more than a small talk if you want your boyfriend to come out of his shell. You also need to ask a lot of followup questions as well.

One way to encourage your boyfriend to talk is to ask questions that are not answerable with yes or no. That way, he will have no choice but to talk more than just one word.

This is not to generalize all men since some guys are more than happy to talk about themselves. For those guys who uncontrollably chatter on and on, these questions will steer the conversation into a meaningful one.

Every guy is different so some questions may not work for your boyfriend. But it’s worth the try. After all, it’s the effort that matters.

So here are 209 great questions to ask your boyfriend:

Funny questions to ask your boyfriend

  1. How often do you go into a room and forget why you went into the room?
  2. How often is your brain on autopilot?
  3. What names were ruined for you because you knew someone terrible with that name?
  4. What’s the most stress relieving thing you can get/do for less than 20$?
  5. What’s the grossest thing you’ve drunk?
  6. What’s your favorite waste of time?
  7. Where is the craziest place you have danced?
  8. What silly thing do you take a lot of pride in?
  9. If animals were as intelligent as humans, what types of jobs would certain animals be uniquely qualified for?
  10. Do fish have necks?
  11. What’s the weirdest celebrity crush you’ve ever had?
  12. If you were a vegetable, what vegetable would you be and why?
  13. What’s the weirdest conversation you’ve ever overheard?
  14. What would your dream mansion look like?
  15. What would you do if a guy asked for your number?
  16. What kind of ice cream describes you best?
  17. If you owned a boat, what would you call it?
  18. What’s the story behind your last Instagram photo?
  19. What’s worst first date you’ve ever had?
  20. If you could choose a superpower, what would you choose?
  21. What crazy things will you do if you ever become rich?
  22. What’s the last thing you Googled?
  23. What’s the weirdest wrong number text or phone call you’ve gotten?
  24. If you could change your first name, what would be the most epic name you could choose?
  25. What should be the next advancement in shoes?
  26. What would you do first if you gained the ability to fly?
  27. What is the coolest flag in use?
  28. If you had a secret lair like Batman or Superman, what would it be like?

Personal questions to ask your boyfriend

  1. What’s the worst dream you’ve ever had?
  2. What do you get overly emotional about?
  3. What event made you mature as a person the most?
  4. What’s one thing that you’ve never told anyone?
  5. What’s something you believe that most people don’t?
  6. Is there anything you’re afraid of in life?
  7. What’s your biggest regret?
  8. Who is your favorite family member?
  9. What’s the best way to earn somebody’s respect?
  10. What’s your best memory from growing up?
  11. What is your favorite thing to do in your spare time?
  12. Who of your friends do you like to spend time with the most?
  13. What was your favorite toy?
  14. What makes life worth living to you?
  15. What’s your favorite animal and why?
  16. If you had to leave your house, what is the one thing you would take with you?
  17. What tv show could you binge-watch all day?
  18. What’s the hardest truth you’ve come to grips with?
  19. What quirks does your body have?
  20. What music do you like that you wish you listened to more?
  21. How soft are you?
  22. What are you a snob about?
  23. What makes you the happiest?
  24. What would it look like if you fully lived up to your potential?
  25. How do you fight off procrastination?
  26. What’s your jam?
  27. How easily do you change your opinions?
  28. What makes you feel alive?
  29. What traits do you like about yourself?
  30. If you could change one thing about your life, what would it be?
  31. What is one thing that you wouldn’t change about your life?
  32. What’s your favorite drink and why?
  33. If you had to eat the same food for a month, what would it be?
  34. Where would you live if money and work were not a factor?
  35. Do you prefer to listen to your heart or brain when making important decisions?
  36. What would you do if money and work were not factors?
  37. Who is one person you wish you could be?
  38. Who is someone you looked up to as a kid?
  39. What’s the best piece of advice you ever received?
  40. What is your biggest pet peeve?
  41. If your life were a movie, what would it be called?
  42. What is one thing on your bucket list?
  43. Would you ever quit your job to travel the world?
  44. What are three words you would use to describe yourself?
  45. In what situations do you act least like yourself?
  46. What word describes you better than any other word?
  47. What are you really obsessed about?
  48. How often do you get into arguments with people on the internet?
  49. What do you want to get out of life?

Romantic questions to ask your boyfriend

  1. Do you believe there’s one person you’re ‘meant’ to be with?
  2. What’s one difference between us that you absolutely love?
  3. What’s one similarity between us that you absolutely love?
  4. Is love something that scares you?
  5. What’s one thing you want to do together that we’ve never done before?
  6. Where is your favorite place to be with me?
  7. What song makes you think about me?
  8. Was it love at first sight with us?
  9. What’s a new nickname/pet name that you would like to call me?
  10. Which trait of mine drew you towards me?
  11. How did you feel when we had our first kiss?
  12. Do you prefer a good hug or a good kiss?
  13. If our relationship ended, what’s the one thing about it you’d miss the most?
  14. What’s one thing you feel our relationship is lacking?
  15. Do you think I’ve been vulnerable in our relationship?
  16. Do you think I’m the ‘right’ person for you? (If yes) What about me makes me the ‘right’ person?
  17. What do you think I’d say is your most attractive quality?
  18. What’s the most romantic movie you’ve ever seen?
  19. What is the number one best thing about our relationship?
  20. What’s your favorite way to receive affection?
  21. Do you want a big wedding or a small one?
  22. What’s your favorite way to show affection?
  23. What’s the sexiest dream you’ve ever had about us?
  24. Do you think you’ll ever want to settle down and have kids?
  25. If we could go anywhere together right now, where would you want to go?
  26. How do you think we both have changed since we first started dating?
  27. What about us is both exactly the same since we first started dating?
  28. What about us do you think works well together? How do we balance each other out?
  29. What does love mean to you?

Flirty and dirty questions to ask your boyfriend

  1. What do you see when you close your eyes kissing me?
  2. Would you hold my hand in public?
  3. Where is your favorite place to be massaged?
  4. Would you kiss me on the neck?
  5. How many times did you want to kiss me before our actual first kiss?
  6. What part of my body do you like the most?
  7. Guess what part of your body I like the most.
  8. When was our most romantic kiss?
  9. Do you like to cuddle?
  10. Would you ever go skinny dipping with me?
  11. How would you describe the way I kiss?
  12. Would you rather hug for 5 seconds or kiss for 1 second?
  13. Do you like it when I touch your face?
  14. Would you ever take a bath with me?
  15. What is your favorite sexual feature of mine?
  16. What do you feel when you look into my eyes?
  17. What was your feeling when we had our first kiss?
  18. Where is your favorite place to be kissed?

Cute questions to ask your boyfriend

  1. If you could describe me with three words, what would they be?
  2. Is there anything you dislike about me?
  3. Does it make you smile when I send you a text message?
  4. Do you think about me during the day?
  5. What reminds you of me?
  6. What kind of movie do you like us to watch together?
  7. Do you think someone can be too much in love?
  8. What was your first impression of me?
  9. If I was really sad, what would you do to cheer me up?
  10. Do I make you want a future with me?
  11. If I was scared, would you hold me?
  12. Would you ever take me out on a picnic under the stars?
  13. What is your favorite pet name for me?
  14. What is a quirky thing about me that you love?
  15. If I looked completely different, would you still love me?
  16. Do you think I’m cute?
  17. Do I look cute while working out?
  18. If I was a dessert, what would I be and why?
  19. How would you describe the way I smell?
  20. What did you think to yourself after our first fight?
  21. What kind of future do you see between the two of us?
  22. Do you like to hold my hand?
  23. Do you feel warm when we hug?
  24. Do you like the way I walk?
  25. Would you ever write a song for me?
  26. Have you ever had a dream about me?
  27. Would you risk your life to save mine?
  28. Do you think I’m pretty?

Random fun questions to ask your boyfriend

  1. Hotdog or hamburger?
  2. Ice cream or milkshake?
  3. What would the title of your autobiography be?
  4. You can only wear one thing for the rest of your life. What do you choose?
  5. If money were no object, what would you have for breakfast every day?
  6. If you could have dinner with three people in the world, who would they be?
  7. What’s a dirty habit that you can’t get rid of?
  8. What you rather eat McDonald’s or a nice, healthy meal?
  9. What’s the weirdest celebrity crush you’ve ever had?
  10. What would you do if we were in zero gravity?
  11. What’s the funniest screw up you’ve ever seen on social media?
  12. If someone had something on their face, would you tell them?
  13. What’s the worst purchase you’ve ever made?
  14. Best purchase?
  15. Do you think I would look sexy with glasses?
  16. Who is your favorite cartoon character ever?
  17. If you could throw anything against a brick wall, what would it be?
  18. You just found five dollars on the ground. What do you do?
  19. Would you rather live in a cave or under the sea?
  20. If there was only one cookie left, would you give it to me?

Asking your boyfriend the above questions will help you get to know him more. It’s a fun and better way than trying to figure out answers as you go.

If you or your boyfriends get uncomfortable with some of the questions, listen to what your gut tells you. Wait for the right time to ask or totally ditch that particular question.

The questions above are just a guide for you. You don’t have to ask them all or else it might sound like you are interviewing your boyfriend.

Just be yourself and don’t push anything. You’ll find out that time is your best ally. Just wait for the right time because good things come to those who do.

Now that you’ve learned the questions to ask for an interesting conversation, it’s worth learning how to flirt like a pro. Check out our article explaining exactly how to do this. Or read our article explaining how to make him miss you.

NEW EBOOK: Love is the central goal of most of our lives. However, dating is hard. And developing a successful, intimate relationship over the long term is even harder. In Hack Spirit’s new eBook, 30 Dating Secrets to a Successful, Long-Lasting Relationship, we use modern psychology to help you understand what makes a relationship work. Check out the eBook here.

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