Cozy Conversation Starters for Winter (that Aren’t about the Holidays)
Baby, it’s cold outside (well, at least where I am) and if I ask one more person what type of fruit they would be or what color their mood is, I might not make it to the solstice.
And there can be even more than usual need to spark a conversation this time of year. Whether your phone has run out of juice on the Greyhound home or there’s a cutie you want to keep close to your hearth, having some back pocket conversation starters can help turn an awkward moment into a lasting memory.
I’m suggesting we avoid the holidays as a topic in this post because it can become tiresome this time of year, and it can bring forward topics that our counterpart may not be quite ready to share yet. This is not to suggest you should never talk about the holidays, but to give you a few ideas for if you sense that might not be the right place to go.
The Principles
The skill of good conversation is really balancing - sharing from what’s true for you, expressing curiosity about the other person/people, in light of your relationship to them and the setting. It comes more naturally to some than others, and we all have something to learn.
Remember to stay in touch with what you are feeling (you don’t have to narrate your inner world, though) and ask questions! And always follow the energy, which includes falling back into silence if it just ain’t goin’ anywhere.
the conversation starters
Funny
Tell me a silly story about getting stuck in the weather - not every conversation starter is a question, it can be a prompt! Especially if you’re in a lull, the other person probably notices too and will welcome a direct invitation to share
What’s the most hilarious celebrity gaffe this year? - follow up with question about who they mention, such as if they follow them or like them; it’s a sideways approach to getting at interests, or you can draw a connection to a time you made a funny faux pas.
Dreamy
When you’re watching a fire crackling, what do you remember? - this will give you a low stakes glimpse into their stories
What do you daydream about when it’s dark and quiet out? - this one is quick tour of their dreams, big and small
Deep
Describe for me what you see yourself doing next winter. - a good follow up is, “how did you make that happen/get there?” this will open up what they hope for, while leaving space for them to choose how vulnerable to be.
What is the condition of your heart as this year closes out? - asking about our hearts is a soft, but direct way of going deeper with someone
In closing
The follow up, building upon, and returning to questions are key in maintaining the spark of connection. It is not the end of the world if the attempt is a flop, or you make a mistake. It’s all profoundly normal!
We encourage you to practice skipping the small talk with us in a city near you :)
Folks at an actual Skip the Small Talk event