Where my faith and creativity collide! A freedom freelancer, prayerful painter and clarion for Christ.

Meaningful Questions

Meaningful Questions

Someone can invite, hug and show us to a seat of honor, but if they never ask us a MEANINGFUL QUESTION have they really shown that we MEAN ANYTHING to them?

An invitation means nothing if we are not truly welcomed. A hug is as piercing as a slap in the face when it is the prelude to a curse and “that seat” is nothing more than the platform for a lynching setting us up for HANGING not HONOR.

I believe hospitality has been grossly redefined in our culture as the formal invitations to weddings, balls and fundraisers. “Show your invitation at the door”, a fancy set up, and hor d’ oeuvres have replaced open doors, family settings, and “help yourself to anything.” The kiss on the cheek, hand shake, hug and high-five have been reduced to target-kissing(remember Judas and Jesus), the middle-finger masquerading as the gentleman’s grip, a hangman’s noose disguised as an embrace and face-slapping parading as palm planting.

I don’t mean to sound cynical. I am simply sharing some observations. I am not throwing stones. I am collecting them so that they will always remind me that there is a kinder, more welcoming way. Formality is not synonymous with fake unless it positions itself on a platform above, as opposed to among, the people.

Sadly, when I think of environments that are furtile soil for MEANINGFUL QUESTIONS, I do not think of *Martha Stewart settings. (*A name often used as the poster child for AMERICAN HOSPITALITY.) How often have we left “galas” feeling deeply connected to a new friend, had our hearts pricked by the grief of another or walked away challenged to make the world a better place or challenged to become a better person after meeting someone who radiated with purpose from the inside-out?

It is quite the buzz kill when one brings up human trafficking, their own personal struggles with addiction, their dreams of adoption or broken heart of divorce in response to the “work the room questions” like:

How are you? (but not really waiting for or wanting an honest reply)

What do you do for a living or how is work?

How about that game?

What about that political debate last night?

I am guilty of asking all those questions and it is not that those questions are inherently bad. It is just that in my own of journey of “becoming”, of “wanting to go to the grave a life-long learner” I find myself gravitating more and more toward settings where MEANINGFUL QUESTIONS are welcomed and pretty much expected.

When I think of places primed for MEANINGFUL QUESTIONS, I think of:

hospital rooms

camp grounds

car rides


small dinner tables


coffee shops and park benches

homeless shelters


prisons and jails

hikes, walks and strolls

small groups

and the Big “C” Church (** This distinction is made because the “C” Church is not a building, although many buildings house great-clouds of witnesses.)

Even as a little girl, I have always gravitated to the most wounded person in the room. I often scared people away by diving deep way too soon. I have learned and am still learning “good guardrails” while remaining vulnerable (and yes, still sometimes to a fault.)

What I never want to “learn away” is the art of asking MEANINGFUL QUESTIONS.

Here are some of my favorite MOST MEANINGFUL QUESTIONS.

What is your name? Do you know what it means?

What breaks your heart and what are you doing about it?

Who have you learned the most from thus far in your life, good or bad, and have those lessons changed how you live? Is so, how? If not, why?

How do you define success and why?

Do you think there is a difference between living a life of success and living a life with significance? Explain.

How do you define LOVE?

What does this sentence mean to you: “I want to leave beauty marks in my wake.” ?

**I would love to know your answers, as well as some of your MOST MEANINGFUL QUESTIONS. Please let me know in the comments below and share with your friends. I would love to know their “dive deep dialogue” too.

About Katie Wilson

Where my faith and creativity collide! A freedom freelancer, prayerful painter and clarion for Christ. #amwriting #Compel Forgiven and Free Living a life that says: COME AND SEE!

One Reply

  1. Anonymous

    I love this post!!! Thanks for being a friend who asks great questions! One of my favorites taught/caught from Karen Burke is “what brings you hope”? Such a great conversation starter!- Katie T

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