Questions to Get to Know Someone

I often have a hard time getting to know people. I’ve noticed that I tend to be very passive in my relationships with others. I am not great at coming up with good, open-ended questions to ask, nor am I forthcoming with my own personal information. For these reasons, I get along best with people who are very outgoing. The people that know me best are the ones that ask me a lot of questions. The people I know best are those that talk freely and openly about themselves, their likes/dislikes, their hopes and desires, their values, etc. Unless someone offers that information to me, I basically never find out. And if I’m not asked something directly, I don’t volunteer it.

I haven’t given this aspect of my social life much thought. However, now that I am dating someone who is extremely similar to me in values as well as behavior, I find myself in a strange spot. I desperately want to those conversations where you really get a good sense of who someone is at their core, but I don’t know how to initiate such conversations. Part of me is extremely frustrated by this. I want to pout or pull away from the relationship all together. But I’m tired of only doing what’s easy in a relationship. I think it’s time for me to be mature and put in the work. Besides it could be fun to learn how to get someone to open up as well as learn how to express my genuine self without waiting for others to pull it out of me.

So here is a list of questions I’ve been coming up with that will help me to discover the things I really want to know about someone:

  • How would you describe yourself to someone who’s never met you?
  • How do you think a friend would describe you to someone else?
  • How would you like for the world to see you/who do you aspire to be?
  • What about yourself (qualities, accomplishments, etc.) are you most proud of?
  • What are 5 values that are important to you?
  • What are 5 memories that you cherish?
  • In what ways do you think you have grown and changed since childhood/high school?
  • When you are upset how do you like to be comforted?
  • Who are three people (famous or otherwise) that you admire? Why?
  • What is one of your biggest regrets?
  • What is one experience in your childhood/youth that you believe impacted who you are as a person? How did it change you?
  • If you could change one thing about yourself, what would it be?
  • What qualities do you enjoy most in friends/partners?
  • What does your inner voice sound like? What are some common phrases you say to yourself?

These are just a few of the questions that I’d eventually like to ask my boyfriend so that I can get a better sense of who he really is. I may end up just giving him the full list one day and maybe we can both answer the questions for one another. Even if it feels gross and artificial at first, I want to make an effort to step outside of my comfort zone in my relationships this year. I’ve always been a curious person, but I’ve never had the confidence or skill to allow that curiosity to guide me when it comes to people. My natural inquisitive nature is stifled by my social anxiety. I know with practice, though, I will overcome that and hopefully discover even more things that will bring me closer to the people in my life.

6 Polite Ways to End a Conversation | Southern Living

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