Image of the conversation question games Vertellis and Where Should We Begin? and a lit candle

Conversation Questions to Boost Connection with Family and Friends

Do you long to experience deeper emotional intimacy with your loved ones? Try conversation questions!

In recent years I’ve amped up the relational connection level with my friends and family by using a single resource: conversation questions.

The first questions I tried were those found in Vertellis Card Games.

To give you an idea of what Vertellis offers, here are two of their questions.

Regarding the last year:

  • Who would you like to thank?
  • What was one of your best decisions?

Glancing at the Vertellis options on Amazon, I see they’ve also come out with family* and holiday* editions. Those would be fun to try!

This summer, I found a number of additional conversation questions as I read the terrific book, The Power of Moments.*

While reading, I jotted down a number of conversation starter questions to use at some point. They include:

  • Given the choice of anyone in the world, who would you want as a dinner guest?
  • What would constitute a “perfect” day for you?
  • Name 3 things the person beside you has in common with you.
  • Tell someone in the group what you like about them. Be very honest. Perhaps say things you might not say to someone you’ve just met.
  • If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
  • What is the greatest accomplishment of your life so far?
  • What roles do love and affection play in your life?
  • Complete this sentence: “I wish I had someone with whom I could share _____.”
  • If you were to die tonight with no chance to communicate with anyone, what would you most regret having NOT told someone? Why haven’t you told them yet?

I recently found another way to deepen relationships. A game developed by a therapist.

One of my friends is a licensed professional counselor. She told me about a game developed by the world-famous therapist, Esther Perel: Where Should We Begin. Perel’s website says she designed the game  “…to introduce playfulness and storytelling into your next date, dinner party, or intimate get together.

I ordered the game to play with my family during the Thanksgiving holidays. However, I invited some ladies over for coffee recently and we played a round of the game and found its insightful and delightful. You can purchase the game here.

In addition, , there’s another option, a free option.

You can make up your own conversation questions. 

I did this last year. Here are the questions I came up with.

  • If money was no object, where would you go on your next vacation?
  • Is there a skill would you really like to learn?
  • Name something you’ve done that you don’t think anyone else here has done?
  • What trait are you most proud of in yourself?
  • Did you learn anything new about yourself this year?
  • What is the best thing that happened to you this year?
  • Name something you fear?
  • What gives you hope?
  • When was the last time you cried or came very close to it? Why?
  • If you could wake up tomorrow and have one thing in your life be different, what would it be?
  • What would you do if you knew you’d not live until the next decade?

Want some Christmas conversation starter questions?

  1. What was the best present you received in the past 12 months?
  2. What was the best gift you gave this holiday season?

I can’t wait to play Where Should We Begin with my family. I hope you, too, will ask your friends and family some “deep” questions to get to know them better.

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