The questions we’ve suggested will help start a conversation and establish a connection. If your chosen one likes to chat, it’s still worth getting to know him better. Choose the most suitable questions from the list, and you’ll find out how much you have in common.

Questions to Get to Know Him Better

  1. What is your ideal day like? Describe it! This question will help you understand what he enjoys doing and whether you can do things together.
  2. What did you learn too late? This question subtly brings up the topic of past regrets and helps understand his future aspirations.
  3. Do you have any complaints about yourself? What are they? This will help you understand his standards. If he has high standards, he likely expects others to meet them too.
  4. How often do you feel completely exhausted? This is a good indicator of how stressed he is. You can continue the conversation about what tires or worries him.
  5. If money didn’t matter, where would you want to live? This will show how compatible you are, especially if you both want to live in similar places.
  6. Who was the most toxic person in your life? This helps you understand what he considers the worst in people and what behaviors he despises.
  7. What were the last two books you read? If you both read a lot, you’ll have plenty to talk about and possibly discover new books.
  8. What habits of yours annoy other people? It’s useful to know this early, especially if you plan to live together.
  9. What makes you nervous? Ask for examples to understand what makes him uncomfortable.
  10. What angers you more than it should? Knowing this can help you avoid unpleasant situations.
  11. What movie was so sad that you’d never watch it again? This is a great question to learn about his emotional side.
  12. What are the two most important lessons you’ve learned from past relationships? This will give you insights into what he expects from you and how he handles difficult situations.
  13. What disgusting and unhygienic things do people do that irritate you? It’s good to know how clean he is.
  14. Do you have a habit that is rare in other people? Everyone has strange habits, so don’t be judgmental.
  15. What do most people overestimate or underestimate about you? This question reveals how he sees himself.
  16. What should you do but never will? This question can lead to interesting answers and conversations.
  17. What’s the best thing your parents instilled in you? Let him answer without assumptions or negativity about his family.
  18. What are you most looking forward to about aging? This question can elicit either a funny or serious response.
  19. What is the biggest sign of weakness in a person to you? This reveals a lot about how he views the world and what he admires.
  20. What did you try to love but couldn’t? This helps you understand his likes and dislikes.
  21. What distinguishes you from most people? Let him describe how he fits into society.
  22. What was the best mistake you ever made? This can lead to an entertaining story.
  23. If you could drop everything and go on a trip, where would you go? This reveals his travel preferences.
  24. What are the most masculine things you’ve ever done? You might hear some cool and interesting stories.
  25. How do you feel about animals? It’s essential to know if one of you loves animals and the other doesn’t.
  26. What names are ruined for you because you knew someone terrible with that name? Prepare for a long story.

Questions Over the Phone

  1. Which movie changed your view of the world? And which had the worst ending you’ve ever seen?
  2. Who was the most villainous hero and the most heroic villain?
  3. Which game have you spent the most time on?
  4. If you started a podcast, what would it be about?
  5. What’s the strangest thing you’ve seen or heard in the media?

Questions via Text

  1. Do you like your job? Why?
  2. Do you have any pets? If not, would you want one?
  3. What do you think will no longer exist in the world during your lifetime?
  4. What’s the most unpleasant thing you deal with daily?
  5. How curious are you?
  6. What weird hobbies do you have?

Questions on the First Date

  1. What would your ideal life consist of? What’s your dream job, ideal parents, etc.?
  2. What would your ideal weekend look like?
  3. What’s the bravest thing you’ve ever done?
  4. If you could change one thing in the past, what would it be?
  5. Who would you risk your life for?
  6. What’s the most astonishing discovery you’ve made in life?
  7. If your job negatively affected your personal relationships, what would you do?
  8. How adventurous are you?
  9. What’s the most pointless information stored in your head?
  10. When was your last date and how did it go?

Questions About Relationships

  1. What’s the best relationship advice you’ve ever received?
  2. What’s the best and worst thing about long-term relationships?
  3. What’s your number one rule in relationships?
  4. What are your pros and cons as a partner?
  5. What could make you end a relationship? (Other than cheating.)

Life Questions

  1. What are you afraid of in the near future?
  2. Are you a religious person? How do you view other religions?
  3. Do you believe in soulmates?
  4. What was the most emotional event for you?
  5. What makes you feel older?
  6. What do you think is considered normal in society but shouldn’t be?
  7. What would your child have to do for you to disown them?
  8. What do you regret not being told in the past?
  9. What’s the most valuable lesson that should be added to public schools?
  10. If you found out you were wanted for a crime (e.g., murder) you didn’t commit, would you turn yourself in?
  11. When in history do you think was the best time to live?
  12. What’s the most annoying question you regularly hear?
  13. What do you argue about most often?
  14. When is the best period in a person’s life?
  15. What’s the cutest thing you’ve ever seen?
  16. What bad experience should everyone go through in life?
  17. What’s worth spending time on?
  18. What did you reluctantly try once but then became a devoted fan of?
  19. Do you agree that ignorance is bliss?
  20. What advice would you give your present self from the future?
  21. What quickly angers you?
  22. What event made you a more mature person?
  23. What’s the most difficult truth you’ve faced?
  24. What everyday task have you mastered and can do perfectly?
  25. What’s it like to be you?
  26. If your life were a book, what would be the title of the current chapter?
  27. How would you change your appearance if you could?
  28. What makes you feel alive?
  29. What would you do 24 hours before your death?
  30. What can’t you live without?

Fun Questions

  1. What do you think aliens would look like?
  2. What website doesn’t exist but should?
  3. What’s the best conspiracy theory you can come up with right now?
  4. What’s the grossest thing you’ve ever drunk?
  5. If flowers had flavors, what would each color taste like?
  6. If you could put anything on a billboard in the city center, what would it be?
  7. Imagine you have unlimited wishes, but every time you make one, something you love most in the world disappears. How many wishes would you make and what would they be? (You can’t wish for things not to disappear.)
  8. What did you Google today?
  9. If you could change your gender for a certain period, would you? If yes, for how long?
  10. What past event would you most like to see recorded?
  11. If you could be the first to do something, what would your achievement be?
  12. How well would you survive if you suddenly got lost in the forest for two weeks?

Racy Questions

  1. What part of a woman’s body do you like the most? What about on me?
  2. What boldest experiments have you done in bed with a girl?
  3. What’s the most unusual place you’ve had sex?
  4. Do you watch porn? Would you want to participate in filming?
  5. Have you ever had virtual sex?
  6. Do you often have dirty dreams?
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