Your Holiday Conversation Survival Guide

Fa-la-la-la-laaaaa-I-can’t-hear-you. Recommendations for conversations that don’t end with avoiding your whole family.

Patreeya Prasertvit
The Shadow
4 min readNov 22, 2021

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Photo by krakenimages on Unsplash

When I first started my email list over a year and a half ago, my goal was simple: create a moment of connection and put a smile on the faces of those I loved. In addition to short reflections, I included a few links to things that made me think, laugh, or feel something other than the anxiety and fear that ran rampant those days of early COVID.

And with the holidays around the corner, there’s nothing like answering questions about when you’ll finally settle down or have kids, hearing the question “So what do you do” for the umpteenth time, or being stuck next to that one uncle that wants to tell you what’s wrong with this country / kids these days / the internet.

So whether your goal is to start better conversations, be the most interesting person in the room, or simply change the subject altogether, here are a few new pieces of kindling for your conversational hearth (paired with recommendations of things to read, watch, listen to or try in case you have some hours to kill at the airport):

Instead of asking: “How are you doing?”

Instead of asking: “Any travel plans?”

  • 💬 Ask: What is something you love about your city/where you live
  • 🎧 Listen: To a podcast about the history of your city. We recently started doing this with Archive Atlanta and have loved feeling a deep connection to the streets & buildings we pass every day.
  • 👀 Learn: A new language (great conversational fodder at an inter-generational table)
  • 📺 Watch: Taste the Nation — Holiday Edition (Hulu) — I’ve recommended this show in the past, but there’s a HOLIDAY edition! What more could you want than to do a deep dive into holiday traditions and dishes from around the world.
  • 💬 Ask: If we made a family/friend/group cookbook — what recipe would you include and why? (Bonus: actually create it!)

Instead of asking: “So… anyone special in your life?”

  • 💬 Ask: What friendships have been bringing you joy lately?
  • 🎧 Listen: Big Friendship — Brené Brown talks with guests about the challenges of making friends as an adult
  • 👀 Celebrate: Unconventional milestones
  • 💬 Ask: “What’s something big or small that you’re proud of accomplishing this year?” (Bonus: Go first.)

Instead of asking: “What are you grateful for?”

  • 💬 Ask: Which one of these speaks to you? and pass your phone around the table.
  • 💬 Ask: What are things in your life that make you feel more like you
  • 💬 Ask: What’s one thing you really appreciate about yourself? OR What’s one thing you really appreciate about _______ (fill in the name of someone else at the table)?

Instead of falling into sibling rivalries or the comparison game:

  • 📺 Watch: Taskmaster — a British comedy show where celebrities have to perform unusual tasks. (I’ve linked one of our favorite clips, but you can find all 12 seasons for free on YouTube.) Bonus: Try out some of the tasks at home with friends and family.
  • 💬 Ask: What are you committed to not doing right now?
  • 👀 Read: Warren Buffet’s 2 List Strategy for Your Goals and Dreams (via For the Interested)
  • 💬 Ask: What is one dream or goal of yours you haven’t taken action on yet? What are ways we can help or support you?

Instead of debating: “What’s wrong with this country?” or “______ is the problem.”

  • 🎧 Listen: Freakonomics podcast: Why is US media so negative? (Did you know there are many more English words that describe negative sentiment than positive?)
  • 👀 Read: The power of JoyScrolling (+ some recommendations for “good news” sources)
  • 📺 Watch: Only Murders in the Building (Hulu) — a delightful dramedy with Steve Martin, Selena Gomez and Martin Short that the whole family can get into — though PG-13) Then 💬 Ask: Why do you think we’re so obsessed with true crime stories?
  • 🤝 Make a difference (virtually): Grab the gang and do some good together online. Here are a few options: Zooniverse — help identify & count endangered species; Be My Eyes — an app that allows individuals with vision-impairment to connect on demand with sighted volunteers for visual assistance; Wheelmap.org — mark and find wheelchair accessible places in your community or city.

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