10 Questions to Strengthen Friendship

By John Daum
October 17, 2022

Long before our homes had living rooms and dens; even before they had sitting rooms or drawing rooms, most houses had a room called a parlor. A parlor (from the French verb parlé, “to speak”) would contain artwork, family heirlooms, knick-knacks, and a few comfy chairs. That’s it. 

The purpose of the parlor was to have a room set apart for simple chitchat. Sliding doors even allowed the parlor to be cut off from the rest of the house for intimate, private conversations.

The point here is pretty obvious. We used to think conversations were so vital that we had a room in our home for them. We used to value and prioritize conversations so highly that we built a particular room in our homes which was basically named “to speak.”

Times have changed.

Face-to-face, in-person conversations are becoming more infrequent. We text, group chat, self-checkout, and app our way through our day. I’m genuinely expecting the phrase “keep in touch” to evolve into “keep in text.” (How is that not a thing yet?) 

Technology isn’t the problem. In fact, technology can allow us to stay connected to people in ways far superior to the best parlor. We do need some balance, though. There’s just something about face-to-face conversation that doesn’t translate into ones and zeros on our smartphones. The mediums we use to communicate dictate how we communicate. We need to revisit the lost art of conversation.

Here are ten questions to start conversations and strengthen friendships.

(Don’t forget, your spouse/partner/significant other is your friend too. Strengthen that friendship.) These questions can take any relationship deeper.

⚠️ A Word Of Caution ⚠️:

These are relatively serious questions designed to move beyond superficialities and plunge you into meaningful discussions. Work on listening without interrupting or interjecting. Ask good follow-up questions and go where the conversation leads you.

  1. What is something people often misunderstand about you? Why do you think that happens? 
  1. If you knew success was guaranteed, what would you be pursuing in your life right now? 
  1. Outside of family members, who has had the most significant impact on your life? How did they influence you? Do they know this? Have you thanked them?
  1. What year do you think was the best year of your life? Why? What year was the worst year?
  1. If it was possible to go back ten years and give yourself some advice, what advice would you give?
  1. Forget about your chronological age. How old are you emotionally? How old are you intellectually? How old is your soul? 
  1. What textures, smells, and sensations do you find soothing or relaxing? Which textures, smells, and sensations give you the heebie-jeebies? What is your favorite sound? Least favorite?
  1. What in your life do you think will seem the most meaningful when you look back many years from now?
  1. Looking back, what would you consider a key turning point in your life? How did you feel about it at the time?
  1. What is one current trend that makes you hopeful about the future? Why? What is one current trend that makes you think the apocalypse is right around the corner?

Key Quote:

To be on a quest is nothing more or less than to become an asker of questions. (Sam Keen) I hope these questions help you in your quest for stronger, deeper, more meaningful relationships.

Extra Questions If You Want To Switch Any Out

  1. What is something you believe is genuinely mysterious? Do you think we’ll ever find an explanation for it?
  2. What is a belief or opinion that you have recently changed your mind about? What led you to change your mind?
  3. What is the greatest lesson you never learned?

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