• KyleCollins

How to Have Fun Conversations at a Holiday Party

Updated: Dec 23, 2018

If you’re the type of person who can generally keep a conversation going or are not totally freaked out by being in a room full of people in a social setting – listen up!


You have a job to do this holiday season. When you go to a social gathering, whether it’s the holiday office party or family dinner, you can help facilitate new connections and put everyone who’s not so good at social situations at ease by sparking new conversations.


Being social isn’t a skill that everyone has naturally, so if you’ve got it – be appreciative of it, and consider utilizing it to put a little more holiday sparkle out there this season.


And if you’re only kind of good at it, remember: it’s a skill you can develop! This approach might help you break the ice, get some practice and get even better.


The tried-and-true Conversations Starters below can kickstart the process for you. Here’s how to use them to full effect, using the Start. Sort. Style. steps.



The Start. Step

Let’s acknowledge why this can be a challenge. Oftentimes, social conversations are stale and people in groups are awkward because they need something to rally around. Something (or someone) that helps set the tone, lets everyone take a breath, and gets the social setting moving a little. That person can be you.


What do you need to do it well? A fresh perspective. Consider the tone you probably want to help set this holiday season: fun and light, with nothing super sad, serious or controversial, but still meaningful. You don’t want to indulge in completely surface-y topics, to sit around and just talk about the weather, or (at a work event) just to talk about work drama all night. Bo-ring!


You do want light and fun but substantial chats to make people comfortable (honesty and a little vulnerability is good!) and facilitate authentic relationships. Fellowship, really.


In order to achieve this, you’ll want to be alert, but relaxed and in the moment. Your goal is to step outside of the casual chatter of the day (which, these days, can include controversial, jaw-tightening topics like politics) and find some more general topics that can encourage people to talk, think, laugh, play, and get to know new sides of one another.


Got your mind right? Are you clear on the purpose of this and why it’s important? Ok, let’s keep going!



The Sort. Step

Check out these Conversation Starter questions to spark some ideas. Pick your fave(s) and drop them right in the middle of a group of people, prefaced by the sentence, “Some friends and I were talking about this the other day, and I’d love to hear your take!”


Conversation Starters: Fun, in general

Works for: Holiday Office Parties and Family Events

  • If you could eat one meal or dish & it be calorie-free for you forever, what would it be?

  • You only get one type of dessert for the rest of your life. What would it be?

  • How much money would it take to get you off of all social media forever?

  • You wake up with an extra one million dollars in your bank account. What is the first thing you’d splurge on?

  • If you were invisible for one day, where would you go first?

  • You have to delete the entire catalog of one pop singer or band forever. Whose is it?

  • What secret (maybe tiny, strange or odd) skill do you have that 90% of the population probably doesn’t?


Conversation Starters: Holiday-related

Best for: Holiday Office Parties

  • What’s your number one favorite thing about the holidays?

  • Are you big into holiday traditions, or do you and your family like to keep it fresh each year?

  • What holiday movie can you watch over and over again and never get sick of seeing? (Or holiday song, to hear)

  • What’s one thing about the holidays that you wish you could do every month?

  • Christmas gets a lot of love, but what other holiday do you think we should make a bigger deal?


Conversation Starters: Holiday-related

Best for: Family Events

The idea here is that you can go deeper and more meaningful with the ones you know and love.

  • What’s your number one favorite thing about the holidays?

  • What traditions of ours do you really like best?

  • What was Christmas like when you were a kid? (So good for grandparents.)

  • What’s the best Christmas gift you've ever received – or given?

  • What’s one crazy memory about a past Christmas that still makes you smile?

With your questions in mind, keep these things in mind when you put them into motion!



The Style. Step

  • Keep the conversation positive. Swirling in negativity is never fun (for long). If something dips down to being too super sad or serious, let it ride for a moment, but then bring it back up!

  • Listen intently. Don’t be that guy or gal that’s looking over the shoulder of the person you’re talking to just to see who else is around.

  • Ask follow-up questions. Be genuinely interested. Slow down.

  • Don’t hide behind the question: answer it yourself, when the time is right, and challenge yourself to relax and let the conversation flow. (This is not an interview.)

  • Mix and mingle. At work events, make sure you’re talking to and including people you don’t see or departments you don’t work with directly each day. Challenge yourself to get to know one, two, or three new people. (And remember their names!)

  • Be patient. Especially at family events, give full attention to the person you’re talking to, and let them go at their own pace. It might take an older member of your family a moment to tell their story. That’s OK! Slow down.

  • As others walk up to the conversation, or if you see them see you talking, bring them into the conversation and quickly get them up to speed on what’s transpired so far, so they can feel included and can enter the flow more easily.

As you volley up the Conversation Starters and help keep the conversation balloon in the air, you can get to know a lot of interesting things about the people around you. It might open up new avenues of friendship, fellowship and camaraderie that you can facilitate, nurture and feed not only during the holidays – but everyday!


Let us know how you do! What were your favorite topics – and which ones do you think we should add here? Email us or DM us on Instagram!

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