25 Questions To Get To Know Someone Deeply

Do you struggle to develop deep, meaningful relationships? Whether you're trying to strengthen 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 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 the most proud of?
  • What are you the most ashamed of?
  • If you could go back and change 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, accepted, and loved?
  • Do you think your parents did a good job raising you while you were growing up? Why or why not?
  • What's one thing that you wish people understood about you?
  • What is your biggest flaw?
  • 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 a 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 happy with your job, or would you rather be doing something different?
  • If money were 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 or influenced?
  • What's one thing that you do on a regular basis that you hate doing, but nobody knows that you despise doing it?

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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. Online counseling is an excellent way to work on your social skills even if you struggle with Social Anxiety. Betterhelp.com offers convenient online counseling that can help you meet your relationship goals - whatever they may be.

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