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Revised and Updated: 365 Connecting Questions for Couples
Marriage365 Book: 365 Self Discovery Questions

13 Self Discovery Questions Everyone Should Ask Themselves

The journey of becoming self-aware is the process of self-discovery and that starts by asking yourself great questions.

Self-discovery is the pathway to building greater confidence in our lives, but it seems like we are too busy these days to stop and check-in with ourselves. The ever-demanding work commitments, kid’s sports schedules, 24-hour news coverage, the time suck of video games, the latest binge-worthy Netflix show, not to mention the family gatherings and house projects…we’re just exhausted. For most of us, we wake up checking our phone, move through the day, and fall asleep scrolling through social media’s endless feeds. These activities occupy most of our time as we bounce from one distraction to another, and it’s killing us. Like a cat with a laser pointer, we chase after the next shiny object, and the next one, and the next one. We’ve lost the art of reflection, gratitude, and awareness.

So we wanted to give you some open-ended questions to ask yourself this week that will help you start the process of discovering what you think, feel, and want in life. If you’re longing to be emotionally healthy, these questions will help jump-start the process.  

  • Who is someone from your childhood that showed you a lot of love? What is an example of what he/she did that made you feel loved? 
  • What motivates you when you’re feeling challenged or stuck? 
  • Do you think that the more money someone has, the happier they are? Why or why not? 
  • Do you ever feel taken advantage of by someone in your life? Explain. 
  • Think about your first sexual experience. What sort of feelings did you have? Examples: safe, loved, abused, awkward, sad, respected, confused, etc. 
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  • What are two areas in your life that you are insecure about? What is something that you can do to build more confidence in those areas? 
  • Do you struggle with comparing yourself to others? Who do you compare yourself to and how does that impact you? 
  • Do you trust the media or do you question there are underlying agendas and sources of information? 
  • How do you deal with negative people? Do you think your actions towards them are helpful or harmful? Think of a specific example to guide your answer. 
  • What is one personality trait that you typically don’t get along with and why?  
  • How often do you consider how your actions might affect other people before doing something? All of the time, sometimes, or rarely?
  • Do you have a difficult time setting limits and boundaries with your family? Why or why not?
  • In regards to past romantic relationships, what would you do differently if you could do things all over again? 

Do something for yourself and your emotional health!


Get more questions in our book 365 Self Discovery Questions here!


Written by Meygan Caston 

Meygan Caston is the co-founder of Marriage365 and lives in sunny Southern California with her husband Casey, their two children, and dog Hobie. She loves her family, the beach, writing, spa days, and helping couples connect in their marriage. Her life long dream is to live with the Amish for a month, walk the Camino, and have lunch with Brené Brown.

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