[Flirty*] 51 Personal Questions to Ask a Guy to Start a Deep Conversation

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51 Personal Questions to Ask a Guy to Start a Deep Conversation

If you’re ever stuck on what to ask a guy, here are some various type of good questions to get to know him better. Perhaps start with some lighthearted questions such as his favorite sports team or TV show. Once you’ve got the conversation going, you can start asking more personal questions like his views on relationships or what he looks for in a partner. However, it’s important to remember that everyone is different, so don’t be afraid to mix things up and ask him whatever you’re curious about.

Questions to Ask a Guy
Questions to Ask a Guy

Questions About Childhood Memories & Dreams

  1. What’s one of your favorite memories growing up?
  2. If you could go back in time and pick one friend from childhood to spend another magical day with, who would you pick? How old would you be?
  3. Who did you look up to the most and why?
  4. Did you prefer to spend time with one friend or a big group of people?
  5. What age were you when you had your first kiss?

Questions About How You View Yourself and Life

  1. Are you happy with your career path or think you might make a change?
  2. What’s something that you find unattractive in a person?
  3. Is there a habit you’d like to change in your everyday life?
  4. Do you have any regrets about the way you’ve treated someone?
  5. If the people in your life were asked to describe you in just one word, what word do you think they’d choose?

Questions About the Future

  1. In what ways do you think our relationship and lives in general will change after marriage and kids?
  2. Do you want to become “best friends” with your child or keep yourself as the provider/disciplinarian?
  3. Would you prefer to spend your retirement working less, doing something you love? Or just relax?
  4. What is one big goal you want to reach by 30/40/50 (insert age)?
  5. What’s your belief/philosophy when it comes to raising kids?

Deep Questions About Difficult Topics

  1. Do you prefer to avoid conflict and not talk through issues if there’s a big relationship struggle?
  2. Do you let how others view you affect your opinion of yourself?
  3. Would you like me to give space when you’re working on everyday challenges or do you like a lot of support?
  4. What was the last thing that made you cry?
  5. Do you ever question a moment in your life that seems wrong now, but maybe didn’t then?

Fun Questions

  1. If you ever won the lottery, what’s the thing you’d have to buy first?
  2. What activity is the most private for you (that you like to do alone)?
  3. What’s the one superpower you think would help for your life situation?
  4. Have you ever watched a movie you’re too embarrassed to admit you liked?
  5. Do you believe in love at first sight?

Fun, Sexy Question to Ask

  1. Are you comfortable “talking dirty”? What does that mean for you?
  2. What is your top sexual fantasy?
  3. Are you comfortable with watching certain types of videos with me?
  4. Are you okay with bringing props into the bedroom?
  5. What do you think of slow, sensual sex?
  6. What is your favorite sexual position?
  7. Would you be turned on if I woke you in the middle of the night to have sex?
  8. If I offered to dress up as anything or anyone in the bedroom, which outfit would you pick?

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More Personal Questions to Ask a Guy

  1. What is your favorite question to ask a woman on a first date? Why is it your favorite question?
  2. What is your favorite book, and why?
  3. Do you smoke, or did you used to smoke?
  4. Do you like to travel? If so, where have you traveled to, and what was your favorite destination so far?
  5. If you could go on a trip tomorrow to anywhere in the world, where would you go?
  6. Do you prefer the mountains or the ocean? Why?
  7. What is your favorite motivational quote?
  8. Are you a morning or a night person?
  9. Are you more like your mom or your dad?

Flirty Questions to Ask a Guy

  1. Do you remember how you felt when we kissed for the first time?
  2. What is your favorite part about my body?
  3. Is there something you’d like to do in the bedroom that we haven’t tried yet?
  4. Do you think we need to work on our physical intimacy?
  5. Do you prefer to be touched somewhere specific?
  6. How many times a week should we be intimate with each other?
  7. How important is sex to you in a relationship?
  8. Are there any fantasies you wish we could act out in the future?

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