40 Interesting Questions to Ask to Really Get to Know Your Boyfriend

Date nights can be really awkward if you don’t know what to talk about. What if you ask the wrong question and make a fool out of yourself? If only you could know the right questions to ask your boyfriend? 

Getting to know someone isn’t really easy, but it doesn’t have to be rocket science either. All you need to know is the right questions to ask your special someone. So, I curated these cute, funny, and deep questions to ask to really get to know your boyfriend. Want to make it extra special? These open when letters or unique and thoughtful gifts for him will be a great gesture to show you love and care about him!

Funny Questions to Ask

Funny questions to ask your boyfriend
  1. If you could have any animal as a pet, what would it be and why?
  2. If you would have to eat only one thing for the rest of your life what would it be?
  3. Who was your celebrity crush as a teen?
  4. Have you ever watched really terrible children’s show just because you were bored?
  5. What’s the worst movie you’ve ever paid to watch?
  6. Name three random things without thinking. Just do it!
  7. What’s the grossest thing you have ever eaten?
  8. What’s something you love that other people think is gross?
  9. If you’re invisible for the day, what would you do?
  10. What did you want to be when you grew up?
  11. Have you ever pretended to be a woman?

Cute Questions to Ask Your Boyfriend

Cute questions to ask your boyfriend
  1. When did you first realize that you love/ like me?
  2. Would you shout my name to the world?
  3. Is there a song you think of when you think of me?
  4. How many times you thought of kissing me before we actually kissed for the first time?
  5. Would you rather hug for 10 seconds or kiss for 5 seconds?
  6. Which one would you like the most: kissing under the stars or in rain?
  7. What is a quirky thing about me that you love?
  8. Have you ever had a dream about me?
  9. Would you take a break from doing your favorite thing to spend time with me?
  10. Would you feel embarrassed if I called you a pet name in front of your parents?
  11. Have you ever cried watching a sad movie?
  12. What is your fondest childhood memory?
  13. How old were you when you had your first kiss?
  14. What’s the craziest thing you’ve ever done?
  15. What’s the craziest thing you’d do for me?

Deep Questions to Ask Your Boyfriend

Deep questions to ask to really get to know him
  1. What did you think when you first saw me?
  2. What do you remember the most about the day when we first met?
  3. How long did you think we are gonna last when we first started dating?
  4. What do you think is your biggest fear about our relationship?
  5. What’s the one thing that you love about me the most?
  6. What’s the one thing you hate about me the most?
  7. What’s your favorite memory of us?
  8. What about love or relationships scare you the most?
  9. What’s the one thing you want us to do together that we’ve never done before?
  10. If one of us had to move far away for some reason, would you still give ‘Us’ a chance (do long-distance) or part ways?
  11. What about us is still the same since we both started dating?
  12. What’s the one thing I do that makes you feel good and you wish I’d do it more?
  13. What’s the one thing in your life you would never change for someone, including me?
  14. What’s the one thing you hope happens in the future of our relationship?

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