How to Talk to Anyone: Conversation Tips for Holiday Parties

The first time I was invited to a work holiday party, I called my mom wondering if I could log my hours for it. While I liked my coworkers and will do just about anything to get into the Christmas spirit, making awkward conversation with my boss’ spouse was going to feel like work, so shouldn’t I get paid for it?

My mom gently told me that counting my time eating a nice meal in good company as “on the clock” would be poor form, and she suggested a reframe: Consider the party a chance to get to know my coworkers in a more personal way, using the longer span of social time — unclouded by work duties — to ask more questions and go deeper in conversation. See the gathering as a festive opportunity instead of an obligation.  

With her reframe in mind, I ended up having a wonderful time at the party. The experience inspired me to think of all sorts of holiday gatherings as “festive opportunities” for developing deeper connections with the people in my life.

Here are a few examples of when and how to connect meaningfully over a glass of eggnog.  

The open house

Typically, I avoid gatherings unless I know they’ll contain a quorum of my friends, and once there, I prefer to catch up with people whom I already know instead of meeting anyone new. But not only does life sometimes demand that we step outside our usual social circles, but also it’s a good idea to stay open to new connections. All life-long friendships start somewhere, and friendliness with strangers makes the world a more congenial place.  

A year or two ago, a neighbor hosted a “get to know the street” party by sticking handwritten notes in mailboxes along our block. Because I live in an urban area and this show of neighborliness is rare, I felt compelled to venture out of my comfort zone and attend the gathering. Knowing that I’d be meeting lots of new people, I prepped for more meaningful small-talk and entered the party with a few conversation starters in mind, open-ended questions like “What are your favorite things to do in the neighborhood?” and “How is our neighborhood similar or different from the place you grew up?” Because the party occurred in December, I also asked about favorite holiday traditions, foods, and activities. Having questions at the tip of my tongue helped me avoid awkward lulls and created a gateway for thoughtful conversation and connection.  

The family gathering

Family holiday meals have earned an unfortunate reputation for being fraught with dysfunction. Regardless of how much you can relate to this stereotype, we can all benefit from making our conversations with aunts, uncles, grandparents, cousins and siblings a little deeper. One simple strategy: pose a question for everyone around the table to answer. As 2019 winds down, invite family members to consider the highlight of their past year. Or, ask everyone to share their most memorable Christmas, or the best gifts they have ever given and received. 

Alternatively, play a game together that involves reflection and sharing. A few years ago, my family gathered in the living room, pen and paper in hand, and wrote haikus on various themes, like “family,” “home” or “holiday.” Anyone can write these simple three line poems, as long as they can count to five and seven. Then, we mixed up the haikus, read them aloud, and guessed who wrote each one. The game brought out the sentimentality and the silliness in all of us.    

The work party

A few years ago, I gave myself a mantra to repeat anytime I enter a social situation that I’m not totally jazzed about: There is no person with whom I have nothing in common or nothing to learn. This mantra has made conversation at parties more fun as it has instilled in me a greater desire for connection and pushed me to go deeper in conversations (asking questions like: what are you reading these days? What do you like most about your work? And my personal favorite, what rabbit holes do you always go down?). 

Thanks to this frame of mind, I’ve devoured books/movies/podcasts that I would have never discovered otherwise, I’ve learned about lines of work that I didn’t know existed and I’ve heard tender stories about individuals’ childhood, vocational discernment and family. And, I’ve left the social gathering feeling like the time was spent in a worthwhile way.   

The holidays present us with an array of festive opportunities for social interaction. Make the most of these moments by asking good questions, listening closely, and seeking moments of connection.  

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