I’ve never been one for small talk. I am always seeking after a deeper, more meaningful conversation. The problem with small talk is that it’s completely generic; the same conversation can be had with anyone with nothing meaningful taken away on either side, at best leaving the relationship at the same level of depth as it was before the conversation began. 

Worse yet, small talk can dismiss the realities of the human being with whom you’re afforded the opportunity of connecting. Asking the high school senior who’s on the precipice of the unknown, “So, where are you going to college?” or the newlyweds, “So, when will you have kids?” takes what should be a celebratory day of connection and instead confronts people with an undue and unfair cultural expectation without context, empathy or interest in their actual lives.

Small talk is a protective barrier to connection and relationship. It serves as a defense mechanism, protecting us from sharing our lives with someone with whom we don’t share a deep relationship.

We are able to keep the person we’re conversing with at arm’s length by chatting about the logistics of our life (relationships, jobs, weather, local sports teams) and cleanly avoiding the more complicated truths of our lives, and thereby, their potentially unwanted judgments or reactions. 

What if this year, as we gather with family and friends to share a meal and welcome the holidays, we had real conversations? What if we felt known and aimed to know others more deeply around our holiday table? What if we left feeling filled up, not emotionally depleted? What if we formed deeper connections with the people we gather with at the holidays?

Of course, you can start by simply asking meaningful questions that dig deeper than the surface, but often starting a deeper conversation out of the blue feels vulnerable.

Meet the Author

Colleen Cook works full-time as the Director of Operations at Vinyl Marketing in Ashland, where she resides with her husband Mike and three young daughters. She’s an insatiable extrovert who enjoys finding reasons to gather people.

I’ve found that it helps to turn deeper conversation into an intentional activity, until deeper, more intentional conversation begins to happen organically. Try asking a couple of questions to the group around your table. Or, place conversation cards at each seat with a few questions to ask each other intentionally. Alternatively, ask each person to write a question down and place it in a bowl and people can draw them out as they dine. 

When you’re simply chatting with someone, you can take small talk into big talk by listening well and asking intentional questions. For example:

“Tell me more about…” 

“What are some of the challenges of…?” 

“What’s your favorite aspect of…?”

“That sounds exciting! What are you most eagerly anticipating about…?”

If the conversation is at a lull, consider sparking a new conversation with some of these questions. (These questions also work great as conversation cards!):

  • “What has been bringing you joy in this season?”
  • “What is challenging you right now?”
  • “Thinking back on your life thus far, what season of your life has been your favorite?”
  • “What have you read that you recommend, and why?”
  • “Who is inspiring you right now?”
  • “When you think ahead 5, 10, or 20 years from now, what do you hope for?”
  • “What’s something you’d like to accomplish before the end of this calendar year?”
  • “Thinking back to past holidays, tell us the story of a meaningful gift you received.”
  • “Share something about yourself that might surprise some of us.”
  • “How are you spending your free time in this season?”
  • “For what are you most grateful for today?”
  • “If we were making a time capsule today to be opened in 100 years, what would you put inside?”
  • “What has made you laugh the hardest recently?”
  • “Tell us the story of an embarrassing moment.”
  • “Describe the moment you’ve felt the most proud.”
  • “What are you looking forward to next year?”
  • “Tell us about something that’s making your life more awesome right now.”
  • “What are you learning about?”
  • “What’s a goal you’ve set for yourself, and how are you doing with it?”
  • “What does a day in your life look like, typically?”

This is just a start, but the biggest key is not to leave it here. Once you get talking, stay engaged, ask follow-up questions and share of yourself in exchange. We are designed for relationship, but sometimes we take a little nudge.