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20 Questions That Lead to Deeper Connection


By now I think it’s pretty clear how much I heart writing about ways to have deeper connection with our friends and family. An important part of self care is cultivating and maintaining healthy relationships.  If we find ourselves happily and deeply connected to the people we spend most of our time with, we will find ourselves generally happier.  We will have more peace, we will form secure attachments, and we will definitely have a lot more fun.  
But connection can be difficult.  It takes work, it requires us giving more of ourselves away, it means we have to be vulnerable. Today I’m giving you a tool that you will hopefully find helpful to connect with your loved ones on a deeper level.  These questions go way beyond “how was your day?”  or “tell me the best and worst thing that happened to you today.”  There’s nothing wrong with those questions, but we can learn so much more about someone by asking questions that communicate our desire to really get to know someone…and allow them to know us in return.  
You can plan a quiet dinner with your spouse, or a rowdy night with your Besties and ask these questions.  You can get to know your parents, co-workers, or anyone better simply by asking away. And spoiler alert:  people want to be known.  So choose the right setting and the right question, and this won’t be as uncomfortable as you fear it will…that’s a Bestie promise.  
1.  What is the best compliment you have ever received?
2.  What is the most important thing in your life?
3.  How would you describe the purpose of your life?
4.  What are you most afraid of?
5.  What is the most beautiful thing you have ever seen?
6.  What have you been spending a lot of time thinking about lately?
7.  When did you feel the most scared in your life?
8.  What is something you are struggling with right now?
9.  What advice would you give to your children, or future generations?
10.  If you could have a conversation with anyone, dead or alive, who would it be and why? 
11.  Name something you feel is expected of you that stresses you out.
12.  When was a time you felt embarrassed?
13.  Who are the people in your life you trust the most?
14.  How would you describe your proudest moment?
15.  What is your love language? 
16.  What is something you do very well?
17.  In what ways has fear of failure held you back from doing something?
18.  What is your biggest pet peeve?
19.  Who has been the biggest influence on your life?
20.  When have you exhibited resiliency in your life?
I don’t know about you, but I’m thinking about all the people I now want to have these conversations with.  Who are you excited to get to know better?  Do you have any questions you would add to the list?

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