6 Best Conversation Starters for Your Next Holiday Party

You know that moment at a holiday party when you’re standing by the punch bowl, clutching a sweating glass, eyeing someone interesting across the room, and mentally rehearsing, “So… what do you do?”

Yeah, we’ve all been there. And we all deserve better.

Holiday parties are these magical, messy gatherings full of glittery outfits, overly ambitious hors d'oeuvres, and people you'd actually like to connect with—if only the opening lines didn’t feel so forced. The truth is, a great conversation starter isn’t just about breaking the ice—it’s about opening a door. A well-placed question or comment can turn awkward silence into meaningful connection, surface-level chit-chat into genuine curiosity. And when that happens, even a crowded room starts to feel a little more human.

The good news? You don’t have to rely on tired go-to’s like the weather or holiday travel woes. There are better, fresher ways to spark a real conversation—ones that feel thoughtful, natural, and maybe even a little fun.

1. “What’s something you discovered this year that made your life even 10% better?”

This opener is gold because it gives people room to reflect and share something meaningful—without putting them on the spot. The beauty lies in its flexibility. It could be anything: a new podcast, a habit, a skincare product, a shortcut to get their toddler to sleep, or even just an afternoon walk routine.

This question creates a space for people to share wins without sounding like they're bragging. It's future-oriented but also grounded in their personal experience, which adds texture to the conversation. Even better? It often invites reciprocity. Once they answer, they’ll probably ask you the same—which means you can bond over your mutual obsession with your new noise-canceling headphones or how you've finally cracked meal prep Sundays.

Pro Tip: Research shows that people are more engaged in conversations that allow for personal storytelling. In a 2018 study published in Psychological Science, participants who shared stories felt more connected and were rated as more likable by conversation partners.

2. “If this year had a theme song or title, what would yours be?”

Okay, this one’s playful and personal—but in the best way. Asking someone to give their year a soundtrack or book title lets them creatively reflect on what kind of chapter they’ve been living. It doesn’t require a deep dive into life’s messiness (unless they want to go there), but it opens the door to it if they do.

They might say, “Honestly, probably ‘Survivor’ by Destiny’s Child,” and laugh, or maybe they'll offer something poetic and raw. Either way, you’ve started a conversation that invites humor, introspection, and a little vulnerability.

What works here is that it doesn’t pressure someone to recap their whole year. It’s an invitation to reflect through metaphor—which helps people feel more seen and more creative.

Good follow-ups:

• “What made you pick that?”
• “Was there a turning point or big moment this year that shaped that theme?”

3. “Is there something you used to believe, but totally changed your mind about this year?”

This one is for the thinkers in the room. And don’t worry—it doesn’t have to be philosophical. They could have changed their mind about oat milk. Or decided that early morning workouts are actually their jam (shocking, but it happens).

This question works because it gently pulls people into self-awareness without putting them on defense. It’s not political or heavy, but it can go deep if the moment feels right. It tells you what someone is evolving through, which is often more interesting than what they do.

And here's where it gets fun: the more surprising or niche their answer, the better. You might find out someone finally came around to liking pineapple on pizza, or that they stopped doomscrolling before bed and started reading murder mysteries instead.

This kind of question taps into something called “cognitive flexibility”—the ability to adapt our thinking when new information shows up. It’s a marker of emotional intelligence and a great conversation tool.

4. “What’s something wildly underrated that more people should know about?”

Let’s be honest, people love sharing their hidden gems. Whether it’s an indie film no one saw, a back-alley ramen spot, or a meditation app that doesn’t talk too much—this question gives them a stage to share something they feel passionate about. Bonus: it makes you look curious and thoughtful.

The reason this one is a sleeper hit? It taps into recommendation culture without feeling transactional. You’re not asking, “Seen any good movies lately?” which often leads to blank stares. Instead, you’re asking for something that deserves attention—and people love being the one to put you onto something cool.

Follow it up with:

• “What do you love about it?”
• “How did you stumble on it?”

Also, feel free to share your own. It makes the whole exchange feel mutual rather than interview-like. Conversations are a two-way street, not an interrogation room.

5. “What are you secretly really good at that people don’t usually expect?”

This one’s playful, personal, and downright delightful. It gives people permission to share their quirks and talents—especially the ones that don’t usually come up in day-to-day life. Maybe someone can juggle. Maybe they write song parodies in their notes app. Maybe they can spot a lie from across the room. This is where you discover the fun facts people usually keep hidden.

The word “secretly” makes it feel like you’re being let in on something exclusive. That builds connection. And when someone shares something they're proud of—but don’t often get to talk about—it shifts the energy in the room from polite to electric.

You’ll often find this question makes people light up, and isn’t that kind of the point?

6. “If you had a ‘holiday do-over’ pass, which tradition would you skip—or remix?”

Now we’re getting a little spicy. Most holiday conversations are about traditions people love—which is great. But asking about the one they’d skip or reinvent often leads to hilarious, refreshing honesty. Maybe someone thinks Secret Santa is awkward. Or they’re not here for dry turkey. Or they’re starting a new tradition of solo spa days instead of big family meals—and they’re loving it.

This question gives people space to talk about boundaries, preferences, and reinvention—without judgment. And it often inspires thoughtful reflection about what traditions really matter, what we’ve outgrown, and what we’re building in their place.

You don’t have to agree on every tradition. But showing curiosity about how others are creating meaning in their lives? That’s real connection.

According to Pew Research, nearly 1 in 3 Americans say they’re modifying traditional holiday celebrations to reduce stress or increase joy—like celebrating with chosen family or skipping gift exchanges.

Today’s Eight

1. Curiosity is magnetic. The best way to be interesting is to be genuinely interested.
2. Start with the unexpected. Skip the small talk and go for questions that invite real stories.
3. Don’t ask to impress—ask to connect. Conversation isn’t performance; it’s a bridge.
4. Laughter builds trust fast. A light, quirky question can create instant ease.
5. Mutual sharing beats one-sided interviews. Be generous, not just curious.
6. Vulnerability opens doors. Honest, reflective answers set the tone for real connection.
7. Energy > perfection. It’s less about the perfect line and more about the warmth behind it.
8. Traditions can evolve—and so can the way we connect. Use parties as a chance to reimagine, not just repeat.

Connection Is the Real Holiday Sparkle

You don’t need to be the loudest, funniest, or most outgoing person in the room to have amazing conversations at holiday parties. You just need to show up with presence, a little prep, and a willingness to see (and be seen).

These six conversation starters aren’t scripts—they’re invitations. Use them as launchpads, not lifeboats. Because the most memorable moments this season won’t come from perfectly rehearsed lines, but from shared stories, laughter over something absurd, or that little spark of “me too” when someone opens up about their year.

So the next time you find yourself standing near the appetizer table wondering what to say—remember: connection doesn’t need to be loud, polished, or clever. It just needs to be real.

And if all else fails? Compliment someone’s drink. You might just end up swapping secret sangria recipes and leaving with a new friend.

Here’s to better conversations—and the kind of parties where you leave feeling a little more human.