8 Conversation Questions for Holiday Parties

Are you dreading* your next holiday party because you know you’ll need to start a conversation in English? Good news — I’ve got you covered.
In the United States, the end of November through January is the ‘holiday season.” A period of time full of holiday parties with coworkers, family, neighbors and friends.
That means asking questions and having conversation in English.
In this Confident English lesson, you’ll learn:
- 8 questions to start conversations in English — perfect for holiday parties
- Which questions are best for your boss, your colleagues, or dinner at someone’s home
- My number 1 tip for easy conversations in English
- My NEW favorite conversation starter
After you watch, I want to hear from you. I’m going to ask you my new favorite question. 😉You can share your answer with me in the comment section below.
*to dread means to feel anxiety, fear, or apprehension about something
8 Conversation questions for holiday parties.
Lesson by Annemarie
8 Conversation Questions for Holiday Parties
Let’s start with the most difficult people to talk to at a work holiday party: your boss or senior managers.
You know you should talk with them but you don’t want to (and you shouldn’t) talk about work. Also, you shouldn’t share too many personal details and definitely no life drama.
Here are three questions to spark interesting English conversation:
- How did you become the [job title]?
- How did you get into [career field] initially?
- What’s the best career advice you’ve ever received?
For example, how did you become the Creative Director here? Or, how did you get into finance?
Now let’s back up for a moment. It would be very strange if you walk over to your boss, say hello, and ask one of those questions immediately.
Instead, we usually start with a little chit-chat or small talk like:
- Are you ready for the holidays?
- Any plans for the holidays?
Then, when you’re ready to transition to a more in-depth question you can use a word like ‘so.’
That means starting with hello, are you ready for the holidays. Then after a little small talk, “So I’d love to ask, how did you get into marking initially?”
(So is a great transition word. And I’ve got a whole lesson on how to use this word in English.)
Now let’s say you want to get to know your colleagues better. Or your neighbors. Here are 3 great English conversation questions:
- What podcasts are your into right now? (Similar: What are you binge-watching right now?) → Super popular question
- What do you love/hate about the holidays? (Similar: What do you love/hate at this time of year?)
- What’s the best/most interesting thing you did this year?
Those are great questions for cocktail parties or any more casual holiday event.
But what if you’re invited to a dinner party at someone’s home or a restaurant?
These are more intimate situations with in-depth conversations that should include everyone. A great question you can ask the group is:
- What’s the most helpful invention of the past 100 years? → You could also ask the opposite with ‘What’s the most destructive invention of the past 100 years.’
A similar question would be, “What’s the best life advice you’ve ever received?”
Okay, we have just one more question to go and it’s my NEW favorite question. But before I share it, I want to talk about the secret to easy conversations in English.
A good conversation means you need to have a question AND you need to participate in the conversation, right?
Here’s my number 1 tip:
Be prepared with 2 or 3 questions you would like to ask at your next holiday party AND prepare how you would answer those questions.
99% of the time, when you ask a question, you’ll get an answer and then hear, “And what about you?”
Always be ready to answer your own question.
Now, let’s get to my favorite NEW question for starting conversations.
If you’ve been following me for awhile, you know my previous favorite question was:
What’s the most interesting thing you’ve read/heard recently?
But I’ve got a new favorite conversation starter and this is the question I’ll be using at all my holiday parties this year:
- What do you wish you were doing more of in your life?
I love it because everyone will have an answer and it’s perfect for any situation — a cocktail party, a dinner party, a 1:1 conversation with a friend or colleagues. It works for everyone.
❤️ this lesson? Check out:
Now I want to hear from you and I definitely want to know your answer to my new favorite question.
As we prepare to end 2019 and start a new year, what do you wish you were doing more of in your life? Share your answer with me in the comments below. I’m excited to read them.
Have a fantastic Confident English Wednesday!
~ Annemarie
Get the Confidence to Say What You Want in English
Follow my 3-step solution to speak English with clarity, fluency, and freedom so you can say what you want with confidence.
You'll also get my Confident English lessons delivered by email every Wednesday and occasional information about available courses. You can unsubscribe any time.
More Like This
#336: English Conversations on How Much and How Many | Advanced Vocabulary
Struggling to describe amounts naturally in English? If you keep using “some” and “a lot” in conversations, you might sound repetitive or unclear. In this lesson, you’ll learn precise, natural English expressions to talk about how much and how many.
How to Say No in English Politely (Without Feeling Guilty)
Struggling to say no without guilt? Learn how to say no in English politely—at work and in social situations—without stress. Get confident, professional phrases to refuse requests clearly and kindly.
#335: How to Explain Your Opinions Clearly in English — The Best Professional Connectors
Struggling to express your opinions clearly in English? Learn how to use English connectors to improve English fluency, business English communication, and professional speaking skills.
How to Finally Speak English with Confidence — Even If You’ve Tried Everything
If you’ve been working hard but still don’t feel confident speaking, there’s a reason for it. And here’s how it can change.
How to Be Interesting in English Conversations (Even If You’re Shy)
Do you want to be interesting in English conversations? The good news is, it’s easier than you think & the secret to it might surprise you. I’ll show you how in 6 easy steps.
#334: How to Group Words and Pause for Natural-Sounding English
Struggling to speak English naturally? Discover how to group words effectively using thought groups to improve your English fluency and sound more natural. Learn how to pause and improve pronunciation to make your English speech smooth and easy to understand.
© Copyright 2014-2025 Speak Confident English | Privacy Policy | Terms & Disclaimer | Online Class Policies
Hello Annemarie, thanks again for your excellent lesson. I appreciate your patience and kindness. Wishing you good luck!
What do you wish you were doing more of in your life.
1- I wish I read more books, watched more movies, and had the opportunity to socialize more with people.
2- I wish I studied psychology to understand people better.
3- I wish I spent more time with my children than taking care of the house chores.
Happy New Year to you and your loved ones.
Happy Holidays Everyone! A special Thanks to you Annemarie, for this selfless initiative to help us get better in our day to day conversations. I must confess, I haven’t been a very consistent reader of all of your mails – that has changed now though..haha – I, however, cannot quantify how valuable every one of them has been to me, particularly, the session on “What to say when you don’t know the answer”. You are simply amazing! On your new favorite question, “what do you wish you were doing more of in your life?” My answer would be “Building and… Read more »
My best life advice I’ve received is that if it’s not nice, don’t say it.
What do you wish you were doing more of in your life?
really appreciate to every time have a interesting conversation and lesson thank you
In my life I wish have more travel around the world i’d like to see different peoples lifestyle and In actually I like live in a warm area,
Annemarie! A whole the lesson all sounds inspiring! From a style of talking (a wisdom,optimistic style ) till giving new words and expressions! I completely share! your greatitude to the two key questions(your favourite). Such as “What is the most significant advice your have heard resently ” and “What do you wish you were doing more of in your life”. I know WHY they are your favourite! And I found one more great question (for me). This is “What got you interested (or inspired) in architecture??Sounds light and deep!.. For me ,I wish I were beeing more and more in… Read more »
Hi Artemii, thank you so much for your comment. I’m thrilled to know that these questions resonated with you and that you learned a new one! 😊
I hope you’ll find ways to be more creative and have a creative mindset in 2020. What do you think will help you do that?