25 Questions To Get To Know Someone Deeply

Do you struggle to develop deep, meaningful relationships? Whether you're trying to deepen a friendship that you've had for years, or boosting an intimate relationship with your significant other, well-chosen questions can spark a conversation that can help you to get to know them in a way you never have before. Here are 25 questions to get to know someone deeply.

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25 Questions to Get to Know Someone Deeply

  • What are you most proud of?
  • What are you most ashamed of?
  • If you could go back and reverse one decision in your life, what would it be?
  • What is your biggest dream in life?
  • What difference would it make in your life if you felt completely safe, completely accepted, and completely loved?
  • Do you think your parents did a good job while you were growing up? Why or why not?
  • What's one thing that you wish people understood about you?
  • What is your biggest personal shortcoming?
  • What event in your life has shaped you most as a person, and how did it do so?
  • Have you ever treated a person in a way that you regret? What would you do differently if given the chance?
  • Do you think it's possible for men and women to be "just friends?"
  • Would you rather be rich and lonely or financially destitute with lots of great family and friends? Why?
  • Tell me about something you did when you were drunk that you've never confessed to anyone.
  • If you could change one thing about yourself, what would it be and why?
  • If you knew you would die tomorrow, how would you spend today?
  • Are you truly happy? Why or why not?
  • Have you ever been in love? How do you know, and what was it like for you?
  • When you're home alone and nobody else is around, how do you like to spend your time?
  • What do you want people to say at your funeral?
  • If you could have a conversation with anyone living or dead, who would it be and why?
  • Do you think you're a genuinely good person? Why or why not?
  • How did you choose your current profession? Are you glad with your profession, or would you rather be doing something different?
  • If money was not an issue, how would you spend your time each day?
  • Tell me about your political leanings. Have they changed since you were younger? How were they developed?
  • What's one thing that you do on a regular basis that you absolutely hate doing, but nobody knows how you feel about it?

Source: anniecoops.com

Taking It Further

If you have trouble making social connections or developing meaningful friendships - or if you have a significant other and want to deepen your emotional connection, consider using a professional counseling service. Betterhelp.com offers convenient online counseling that can help you meet your relationship goals - whatever they may be.

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