Conversation Prompts for the Holidays
The holidays can feel like a strange mix of magic and chaos. There are moments that feel like a movie (twinkly lights, warm kitchens, quiet drives home) and moments where you’re wondering how you got roped into the group discussion about someone’s cousin’s neighbor’s dog.
It’s a season full of people, emotion, and often conversations that skim the surface because most of us are tired, overwhelmed, or unsure how to go deeper without stirring anything up.
Plunge offers another way. Whether you’re home for the week, hosting for the first time, navigating family dynamics, or spending the holidays with your partner, friends, or kids, the right questions can open up conversations that feel grounding instead of draining. This guide is here to help you use Plunge in real, gentle moments to reconnect with the people you love and maybe even enjoy yourself along the way.
Blimpin’ Holiday Prompts: Light, Warm, Easy
Blimpin’ is the playful landing zone. It’s the space for simple questions that bring laughter, nostalgia, or shared memories without touching anything too tender. Perfect for car rides, cookie baking, waiting for everyone to get ready, or when you're easing back into a room after a long travel day.
Here are new prompts to help you warm up:
What’s a holiday food you’d happily defend in a court of law?
If you could teleport to any December moment from your childhood, where would you land?
What’s the coziest tradition you wish more people did?
What’s the funniest holiday gift you’ve ever witnessed someone receive?
What’s your favorite weather to experience during Christmas?
These kinds of questions don’t ask for vulnerability. They invite playfulness and presence, which often help everyone settle before the deeper conversations begin. They’re also perfect for first-time partners meeting families, or for avoiding awkward silence when you’ve been asked the same “So how have you been?” ten times in two hours.
Surface Holiday Prompts
Surface questions are where connection starts feeling intentional. These prompts help people reflect, share stories, start to reflect on the sensory experiences and talk about what’s been meaningful without crossing into territory that requires emotional heavy lifting. They’re especially good during evening wind-down chats, after a walk, or when you’re reconnecting with someone you haven’t seen in a while.
Try these:
What’s your favorite holiday tradition?
What’s a tradition you’d love to start, even if it’s tiny?
What’s something from this year you want to leave behind?
Do you have a favorite Christmas song?
What’s something you didn’t know you needed until it happened?
These questions help you shift out of autopilot holiday scripts. They invite sincerity, but gentle enough that no one feels exposed or unprepared. They’re perfect for reconnecting with siblings or deepening conversations with friends who flew in for the week.
Depth Holiday Prompts
The holidays can bring up more feelings than we expect: grief, joy, pressure, longing, hope, exhaustion, all wrapped together. Depth prompts create space for those emotions without forcing anyone to “fix” or respond with advice. They’re best used with people you trust, in moments where you can hold space for each other.
Here are prompts that help name what’s real:
What’s something you’re carrying into this season that you wish someone understood?
Where do you feel a shift happening in your life right now?
What emotion has been sitting closest to you lately?
What’s something you’re grieving softly, even if you haven’t said it aloud?
What’s a hope you’re quietly holding for next year?
These prompts help you speak from the heart, offering a chance to feel witnessed in a season where many people feel unseen or overstimulated. Even one Depth question can change the energy of an entire gathering.
Prompts for Families
Family conversations can be beautiful, chaotic, or somewhere in between. These prompts are great around the table, during a game night, or while you’re trimming the tree and need something other than “crazy weather, huh?”.
Try these:
What’s a family story you never get tired of telling?
What’s something our family does that you hope never changes?
What’s a moment from your childhood holidays that still makes you smile?
What’s something you appreciate about this season that you didn’t notice when you were younger?
If we could create a brand-new tradition today, what could it be?
These questions help families shift into warmth and shared memory. It’s the safe middle ground between small talk and emotional overwhelm.
Long-Distance Holiday Prompts
Sometimes you can’t be in the same room. Flights are too expensive, schedules don’t line up, or life just gets in the way. Plunge makes long-distance connection feel a little less far away.
Here are prompts that work beautifully over video calls, voice notes, or text:
What’s something in your space right now that’s bringing you comfort?
What’s a tiny victory from this week you want to share with me?
What’s something you’re learning about yourself as the year ends?
What’s a tradition you’re doing on your own this year that carries meaning for you?
What’s a moment from this season you’d bring me into if you could?
These questions help fill the gaps created by distance, giving you a way to stay emotionally close even when you can’t physically show up.
How to Use Plunge During the Holidays
The holidays have a rhythm of their own. Sometimes you’re in sync with it; sometimes you’re trying to find your footing. Plunge works beautifully because it moves with you. It doesn’t demand a certain mood.
You can use Plunge in small, gentle moments. When you’re sitting in the car before going inside. When the night is quiet and everyone else has gone to bed. When the energy in the room feels scattered and you want to reconnect.
You can pass one question around before dinner or share a Depth prompt with your partner after a long, emotional day. You can use Playlists to gather your favorite holiday questions and return to them throughout the season. Or start a Guided Dive when you’re curled up on the couch with someone you love, letting the app shape the flow so you don’t have to think about what to say next.
Plunge can help you pause during a hectic day, breathe when you feel overstimulated, or deepen a conversation that feels shallow but ripe for something real. It makes room for softness, clarity, and connection, the very things most of us are secretly craving during this season.
Bring Yourself Home
The holidays don’t need perfect conversations. They need honest ones. The kind that help you feel human again. The kind that remind you why you showed up, why this season matters, why you care about the people sitting across from you.
One question. One moment of presence. One small shift. That’s all it takes.
Plunge helps you find your way there one conversation at a time.
