As a society, we exist in an age of paradox where we simultaneously experience both greater connection and greater disconnection than ever before. And since a sense of belonging is one of our fundamental needs as humans, it’s important for us to be aware of where we fall on the connection spectrum and that we be equipped with tools to connect in more fulfilling ways.
There’s certainly some complexity involved, because fulfilling our need for connection is somewhat dependent on the reciprocation of others. There’s an element to our connection that is beyond our control. Nevertheless, our intention and initiative can open up opportunities for deeper relationship for ourselves and simultaneously offer that gift to others. It can be tempting when wrestling through feelings of disconnect to think that the answer is more connections. And sometimes it’s true. But often times, what we’re really in need of is depth. Deeper connections with the people we’re doing life with already every day.
Here are twenty questions to get you started. They can be tossed into a jar for stimulating dinner table conversation or asked during the unwinding bedtime hour to spouses or children. They work nicely for date nights or dinner parties…essentially anywhere conversations are had.
Our conversations can tend to default to the surface level subjects like schedules and meal plans and play by plays of the day. That sort of conversation is simply a part of everyday life, but without anything else over time it can result in not feeling particularly seen. (At least this has been the case in my experience.)
Questions like the ones below have often helped me to reconnect with those I love, to feel better seen by them, and to help me to see them a little more fully as well.
Meaningful Conversation Questions:
- Tell me about one thing that made you happy today.
- Was there anything that felt hard about your day?
- How would you describe the way you felt today?
- What is something you have been learning lately?
- Is there anything you hope to do better tomorrow?
- Was there anything you did today that was particularly fulfilling or rewarding?
- Use ten words to describe to me what kind of person you hope to be in ten years.
- Walk me through your day by telling me one thing you heard, saw, tasted, smelled, and felt.
- What is something that you’d like to know more about?
- What do you wish that you had more time to do?
- When do you feel the most like yourself?
- What would your ideal day look like?
- What is one thing you can do today to bring goodness of any kind into the world? (Joy, Comfort, Love, Peace, Life, etc.)
- Who is someone you admire? Why?
- What inspires you? (What makes you want to create? What makes you want to become the best version of yourself?)
- What gets in the way of your contentment?
- What people in your life bring out the best parts of you?
- Have you noticed anything that makes you consistently happy and content?
- Have you noticed anything that makes you consistently sad, discontent, discouraged, or frustrated?
- Are you happy with the person you are becoming? Why or why not?
I’ve provided the list of questions above and the same questions available in a printable form below to be cut up and tossed in a jar. (Just to clarify: The printable is two pages, but they’re the same questions on both pages. They’re simply different fonts because those sorts of things matter to me.)
And to offer a bit of background, when I was making this collection of questions, I was imagining them being used by parents of teens and preteens. They’re pretty versatile questions and could certainly be used in any capacity, but I was nannying for that age group at the time and trying hard to find a balance between connection and offering space for independence and ample breathing room. I wanted them to know I cared, but also that I respected their space. It’s a tough season to navigate. And sometimes the typical questions of, “How was your day?” result in one word answers because they just don’t feel that interesting to answer. I think these questions would have been helpful for initiating deeper conversations, even if only for the five minute walk up the driveway after school. It’s my hope that these simple questions might serve as a small tool to help you in maintaining daily connection with the people you care about most.
