Tips for Deeper Holiday Conversations

For as many of my friends who have confided angst at the idea of sitting around a holiday table with family who voted opposite of them in the recent election, there are also those who have just shrugged and said, "I can only wish my family talked about something that actually mattered!"

Two Ways to Go Deeper

Whether you're gathering with those who you are struggling to love and understand or those who tend to stick to small talk, here are two of my favorite ways to invite more sharing and love:

 1) Feature Affirmation: 

With a tendency for family members to feel judged, misunderstood, or left out-- let's make sure that no one leaves our tables not feeling valued!

My favorite way is to put table-tent name cards at each place and ask every family member to write one quality they admire and love about each person inside their name card.  During the meal, leave time to go around the table and have each person read their words out loud.

Here's one of my name cards from a previous year... a gift of love to take home!


2) Go Past the Updates:

Whether you're gathering with family and friends you see often, or people you haven't seen in ages, ask a sharing question that allows everyone to go around and share a bit about their lives.

My favorite open-ended questions are those that invite vulnerability while allowing the person sharing to pick specifically what they feel comfortable sharing.


  1. What has been a highlight (something you're proud of, something that felt good) and a lowlight (a stress, a loss, a disappointment) in your life in the last year?
  2. What is one big thing that has happened in your life recently, and how did you feel about it? And one thing coming up in your life, and how do you feel about it?
  3. What is one thing that has changed in your life this last year, and in what way(s) are you grateful for it?

I always suggest that after each person shares, the best response from everyone else is simply, "Thanks for sharing!" so that we can acknowledge each other without risking advice-giving or getting off track from our sharing.

And bonus for doing this activity as soon as everyone has gathered so it helps set the tone for the whole day/weekend!  Maybe gather everyone around in the living room for an hour during morning coffee or appetizers?

What If It Feels Forced or Awkward?

But it's usually not for lack of actual ideas that we don't facilitate these conversations as much as it because we feel stupid, silly, or awkward leading them.

Chances are high that if your family doesn't typically gather and connect in these ways that you'll get eye-rolls from those who think it's "cheesy" or sarcasm from those who are uncomfortable.  But I'm of the mind that just because something is awkward doesn't make it bad.

I really do believe that everyone wants to be seen.  Sometimes we're afraid of it if it doesn't feel safe or if we fear rejection for who we expose ourselves to be.  But that doesn't take away the need and hunger to belong, it simply reminds us that one of the requirements of healthy relationships: "being seen" (vulnerability) has to be in tandem to another of the requirements: positivity. (You can order my book here for more about all 3 of the relational requirements and how they work together.)

Our family can trigger us like no other because we have a lot more "consistency" with them-- meaning we have history.  That history can lead us to assume more about each other, take things more personally, or not show up with as an open of a mind about how people might be different.  We have expectations and patterns and norms.

Therefore, the only way to get a different outcome after our time together is to change those patterns and norms, a bit.

So, yes, it will feel weird, awkward, or uncomfortable.  But that's only because it's not normal. Yet. And just as we go to the gym and expect to sweat and be out of breath because we value the outcome of being physically healthy; so, too, do we show up at the emotional gyms and push ourselves a bit because we value deeper relationships.

It is my hope, that one week out, you will make a decision to be someone at your holiday gathering who helps everyone share deeper, learn more about each other, and affirm each other in meaningful ways. Whether you're in charge and can set the tone, or perhaps talk to the host/hostess ahead of time and see if they're open to you helping facilitate something, but either way, you can be someone who shows people that they are seen and valued. It's simply a muscle to be strengthened-- you can do it.

May your presence at any gatherings this holiday season help foster more love, depth, and gratitude.