So, the holidays were rolling around again. You know how it is. You get a bunch of people together, some know each other well, some barely at all. I was looking at my guest list for our annual get-together, and I got that familiar knot in my stomach. How do I stop it from being… well, awkward?

I’ve been to too many parties where everyone just clumps up. Same old conversations. Or worse, that polite, strained silence you could cut with a knife. Not on my watch, I decided this time. I had to actually do something. This wasn’t going to be another one of those parties if I could help it.
My Grand Plan (Sort Of)
I didn’t want anything super formal or cringey, you know? Like those corporate team-building things. Ugh. No thanks. My goal was just to get folks mingling a bit, maybe even laughing. So, I started actually jotting down some ideas. This was my “practice run” for trying to make the holiday party a bit smoother, a bit more connected.
First thing I thought was, keep it light. Keep it holiday-themed, but not too specific, so everyone could join in. I came up with a few mental prompts, things I could casually drop into conversations. Then I thought, maybe I’ll write them on little cards and just scatter them around. Yeah, cards sounded less like I was interrogating people. More casual.
Here’s what I jotted down in my little notebook, my secret weapon for the evening:
- What’s a holiday tradition you secretly love, or maybe one you could totally do without? This one always gets a few chuckles and some surprising answers, I figured.
- If you could invent a brand new holiday, what would it be and how would we celebrate it? This one can get pretty wild and creative.
- Best or worst holiday gift you ever received? Or maybe one you gave? Everyone’s got a story for this, good or bad.
- What’s a holiday movie you can watch over and over, and what’s one you absolutely can’t stand? People have strong opinions on this, trust me. It gets them talking.
- If your holidays had a theme song, what would it be this year? This one I thought was pretty fun and a bit different.
I also thought about just having some general, easy ones ready, stuff that wasn’t strictly holiday-focused but still good for getting people to open up a little:

- Anything you’re really looking forward to after the holidays are over? Sometimes people are more honest about that, gives them a laugh!
- What’s one new thing, big or small, you tried this past year that you enjoyed?
Putting it to the Test – My Little Experiment
So, the day of the party came. I had my little mental list, and I’d actually scribbled a few of these questions onto some festive-looking coasters I found last minute. Just left them on the coffee table and near the snacks. No big announcement, no pressure. Just there.
And you know what? It actually worked. At first, people were just chatting in their usual small groups. But then someone, I think it was my cousin, picked up a coaster. Read it out loud. Laughed. Someone else chimed in with their “worst gift ever” story. And just like that, the ice started to crack. Little by little, new conversations sparked up.
I didn’t push it. Just let it happen organically. Sometimes I’d use one to steer a conversation if it was dying down or if I saw someone looking a bit left out. Like, “Hey Sarah, speaking of traditions, got any weird family ones you’re willing to share?” Kept it casual, like it just popped into my head.
By the end of the night, folks who’d barely said hi to each other at the start were swapping stories and laughing. It wasn’t some miracle cure for all social awkwardness, obviously, but it definitely made things warmer, more connected. It felt more like a real gathering, not just a room full of people existing in the same space.
My takeaway from this whole thing? A little bit of prep goes a long, long way. You don’t need to be an entertainment director or force fun down people’s throats. Just having a few easy questions in your back pocket, or on some coasters, can make a big difference. It’s not about forcing interaction, it’s about making it easier for people to connect if they want to. And honestly, I was less stressed too, knowing I had a little something to fall back on if things got too quiet. So yeah, my little experiment with holiday ice breaker questions? I’m calling it a win. Will definitely be doing something similar next year. Maybe I’ll even come up with some new ones. Practice makes perfect, right?
