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Two Important Questions in Life

February is a short month, but full of meaning and important days. It’s Black History Month. It has Groundhog Day, President’s Day, and the Super Bowl. Of course, there’s always Valentine’s Day, which brings up a variety of emotions.

February also holds personal significance for me. My husband and I met in February shortly before Valentine’s Day at a speed dating event that was the backdrop for a commercial, which is a fun story for another time. This year, it’s also been fun reflecting on the wild adventure of life that we’ve been on since that fateful night.

The reminiscing reminded me of an important aspect of our dating. Before meeting my future husband, I came across a book entitled “101 Questions to Ask Before You Get Engaged”. Although I was single at the time, I thought it seemed like a good idea to start answering these questions for myself so that I could gain more clarity in what I was looking for in my life and a potential partner.

A few weeks into our dating, I mentioned to my new boyfriend that I was reading an interesting book and asked if he was curious to know more about it. During our first week of dating, we met for happy hour, than salsa dancing with dinner afterwards, followed by a third date night that involved a meditation retreat on relationships preceding a friend’s party that was also the set for a music video. Given our open-minded and adventurous approach to dating, I figured I could manage any possible embarrassment, be brave, and share the title of the book with this relatively new guy I was dating. It was a moment of truth and integrity for me. Plus, it was a litmus test. I figured the man I would wind up with would be open to going through this book with me.

I took a deep breath and shared the title with him. I’m so happy that I managed my fear and hesitation and asked him.

“Sure,” he gently said with a smile. We both agreed that it seemed like a good way to know more about ourselves and each other.


The book is full of questions designed to stimulate discussion with a potential life partner. Two questions had, and continue to have, an significant effect on me. To paraphrase, the questions are:

  1. “What is the one question that you want to ask me but haven’t asked?”

  2. “Why?”


I love the first question because it leads us to reflection and pushes our comfort zone. When developing a trusting relationship whether that relationship is romantic, professional, or friendly, it’s important to be able to freely, openly, and respectfully express oneself in an authentic manner. For a relationship to grow, we must address inevitable challenges and ideas that push the limits of our comfort zone.

This question is also important to ask of ourselves to aid in our growth and to get clarity on a situation. I continue to ask variations of this question of myself in different scenarios, whether it is with work, at an appointment, or when making a purchase. “Is there something else I need to know?” “Do I have any other questions that I haven’t asked?” These questions are then followed by the next important one …


Why? This question is asked multiple times by children in their attempts to learn more about the world around them. It’s also a key question in root cause analysis, a quality improvement process that helps determine the cause of an event, issue, or problem. “The 5 Whys” is also a tool adapted for life coaching to aid clients in getting to the heart of a situation.

How we ask why is as important as ensuring that it is asked. Tone has meaning. Go ahead, think of how many ways you can add inflection to “Why?” that adds additional meaning to it. There’s a big difference in asking “Why?” from a space of blame, indignation, uncertainty, or whining versus asking it from a space of curiosity and exploration. I encourage the latter.

Asking ourselves “Why haven’t I asked this question” in a gentle, nonjudgemental manner is an important question to answer. The answer might be simple, such as “Because I just thought of it”. However, asking why can also unearth some underlying thoughts or feelings that might be keeping us from being fully informed and making decisions that truly serve us well. Perhaps we don’t ask the initial question because we anticipate a negative or unsatisfactory response or the question stirs up thoughts or feelings within ourselves that we’d prefer to ignore. Or, perhaps we anticipate a prolonged discussion afterwards that we’d rather skip.

Asking “Why” to ourselves helps us identify what personal limiting thoughts and feelings might be holding us back from the life that we want to live. Approaching the question from a place of compassion helps us transform the resulting answer from either a positive or a negative response into one that, either way, provides us feedback to make adjustments in our approach to life, situations, and relationships.

For me, pushing the boundaries of my comfort zone and asking these two questions of myself and to my new boyfriend provided me with the information I needed to confidently move forward in our romantic relationship. In other circumstances that I’ve applied these questions, I’ve chosen not to move on with the situation. In all circumstances, asking these questions provides me useful feedback to grow and make more informed choices.


  • What question have you been wanting to ask someone or yourself and haven’t?

  • What thought or feeling is holding you back from asking that question?

  • What are you learning about yourself by asking yourself these questions now?

  • How can you use this feedback to move forward in life?

Christie Masters, MD, is a physician and life coach based in Los Angeles. She offers individual and group life coaching and can be contacted at

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