thanksgiving and christmas conversation starters

Make Your Holidays Merrier — 50+ Questions and Conversation Starters for Your Seasonal Gathering

The holidays look different for everybody. While we may share a winter recess from work or school, how we spend that time — and who we spend it with — richly varies between cultures, communities, families, and individuals.

While the ways we celebrate may be diverse, many of our holiday woes transcend time and place — like how to chat with estranged relatives, sidestep tricky tableside conversations, and avoid unwanted awkwardness during dinner. The ensuing anxiety can certainly be enough to turn Santa Claus into Scrooge.


If you find yourself stricken with seasonal nerves, here’s something you might be overlooking: many of those you’ll be celebrating with are probably anxious, too. This year, let’s help keep things calm and bright. Check out these 50+ questions and conversation starters guaranteed to keep the good vibes coming.

It starts with the firsts

If our lives were movies, we would all be the stars of our own feature films. Many of us thrive on our main-character energy — anchoring in our journeys to embrace a narrative arc essential to our identities. And like any good story, we love to share our autobiography with others.

By turning mealtime into an opportunity to ask about the defining moments of each other’s lives, we can show interest and appreciation for those we hold dear. The easiest way to start is by asking about one another’s “firsts” — the essential, early experiences that shaped our paths.


Of course, the ideas for inquests are unlimited. But here are a few safe places to start:

  1. Who was your first teacher?
  2. Who was your first friend?
  3. What’s one of your first memories?
  4. What’s the first place you ever traveled to?
  5. What’s the first song you remember loving?
  6. What was your first dream job?
  7. What was your first cellphone?
  8. What was your first social media account?
  9. What was your first job?
  10. What was your first car?

A few of your favorite things

“Raindrops on roses and whiskers on kittens
Bright copper kettles and warm woolen mittens
Brown paper packages tied up with strings
These are a few of my favorite things.”

While your list of favorites may sound a little different than this classic song, we all have interests and tastes that help define who we are. Yet despite this, we often don’t know all that much about the likes and dislikes of our loved ones. Grandma may have asked for that Barnes & Noble gift card this year, but can you name her favorite author?


We may know which holiday dish each loved one considers their specialty, yet still find ourselves unaware of the fundamental facts that their friends and colleagues consider essential. By simply asking your loved ones what they like, you can strengthen bonds, find unlikely common ground, and help make everyone at the table feel seen, heard, and welcomed.

Here are a few questions you can start with to learn more about your loved ones:

  1. What’s your favorite emoji?
  2. What do you think is the best fashion trend of all time?
  3. What’s the best thing that happened to you this year?
  4. What movie or TV show do you always find yourself going back to?
  5. What band or musician could you not live without?
  6. What book or author do you love the most?
  7. What quote do you live your life by?
  8. What celebrity (living or dead) are you most fascinated by?
  9. What holiday food do you most look forward to every year?
  10. What’s your favorite holiday memory?

If & Then inquiries

Hypotheticals may only exist in theory, but asking abstract questions is a tangible way to get to know a person on a deeper level. If & Then conversation-starters prompt guests to imagine what they would do under given — albeit fictitious — circumstances. By asking someone what course of action they’d take in an unbelievable situation, you can learn more about their values, dreams, goals, and even their sense of humor.


Here are a few If & Then inquiries you can ask at the dinner table:

  1. If you could have any career in the world other than your own, what would it be and why?
  2. If you could invent a new holiday, what would it be?
  3. If you could go on an all-expenses paid vacation, where would you go?
  4. If you could choose a musician to write the soundtrack to your life, who would you hire (living or dead)?
  5. If you could go back in time and tell yourself something, what would you say?
  6. If you could live a day as another person, who would you choose?
  7. If you were a piece of furniture, what would you be and why?
  8. If your life was a movie, what genre would it be and who would be the star?
  9. If you could invent something, what would it be?
  10. If you were a superhero, what would your name and powers be?

At Goodwin University, we believe in the value of your personal and professional goals. Our community forms a supportive environment dedicated to helping you develop your potential — enabling you to achieve a meaningful and fulfilling career doing what you love. Learn more about how Goodwin supports student wellness today!


Bests and worsts

No, this game isn’t a competition of winners and losers — it’s a conversation starter to explore each other’s preferences and personal experiences. When you ask your loved ones about not only the best things they’ve experienced, but the comically bad (we stress comically,) you can inspire raucous rounds of tableside reminiscing.


Here are some conversation starters that will keep you guests engaged and enthusiastic:

  1. What’s the best advice you’ve ever been given?
  2. What’s the best meal you’ve ever enjoyed?
  3. What’s the worst meal you’ve ever had?
  4. What’s the worst movie you’ve ever seen?
  5. What’s the best trip you’ve ever taken?
  6. Who was the best teacher you ever had?
  7. What’s the best flavor ice cream?
  8. What’s the best concert you’ve been to?
  9. What’s the worst thing you’ve ever stepped in by accident?
  10. What’s the best surprise you’ve ever gotten?

21st century topics

Perhaps your friends and family are more philosophical than these breezier lines of questioning allow. If you and your loved ones enjoy examining the big picture, you can go a little deeper by asking questions about some of today’s hottest topics.


You can facilitate a profound conversation by asking a few of these questions:

  1. How is AI changing the world around us?
  2. What will the world look like in twenty years?
  3. What would someone from 200 years ago be surprised by today?
  4. Are people becoming too dependent on technology?
  5. How can social media both hurt and help relationships?
  6. Why don’t people read as much as we used to?
  7. What kinds of technology do you think the next century will see?
  8. What challenges do children today face, and how do these compare to previous generations?
  9. Are people becoming more impatient as technology and society become more efficient?
  10. What would life be like if the internet ceased to exist?

Wild card questions

Sometimes, the best conversations come simply out of pocket. After all, holiday talk doesn’t need a strict theme or structure to inspire a feel-good vibe.


Try your luck with these spontaneous, easy-going conversation starters to learn and laugh while the good times roll:

  1. What animal best represents your personality?
  2. What’s the funniest thing that’s happened to you at work/school?
  3. What’s your guilty pleasure song?
  4. What’s something a lot of people don’t know about you?
  5. What’s the funniest thing you ever believed was true, only to find out you’d been mistaken?
  6. What’s something you strongly associate with your childhood?
  7. (Choose a common item). What would you have called it if you were in charge of naming it?
  8. Describe yourself in 1-3 sentences without using the letter “e”.
  9. What piece of furniture do you most strongly identify with?
  10. What’s the emoji you overuse the most?

Bonus round — reindeer games

While asking the right questions might make your gathering merrier, you can always go off script with an inclusive and engaging conversational game.


These simple activities will curate a great vibe and unforgettable occasion for everyone involved. Better still, they’re cost-free and don’t come with those pesky, easy-to-lose trinkets.

Two Truths and a Lie

A time-honored icebreaker, Two Truths and a Lie provides an easygoing opportunity to become more familiar with new friends and old acquaintances alike. The premise is as sweet and simple as apple pie (or whichever seasonal dessert might tickle your fancy).

Stop us if you’ve heard this before: your guests think up two little-known facts about themselves and one lie — leaving listeners to determine which of their three alleged truths is, in fact, a fib.


Would You Rather…

You’ve likely played Would You Rather more than a few times. While it may not go down in the books as a holiday go-to, this game has the benefit of being customizable to the tone of your gathering. Choose your adventure — the conversations you start can be wholesomely above-board, outlandishly absurd, or earnestly thought-provoking.


Not sure where to begin? Here are a few indispensable Would You Rather questions to engage your guests this holiday season:

  • Would you rather live in space or live in the ocean?
  • Would you rather permanently give up sweet or salty foods?
  • Would you rather have a free personal chef or a free on-call chauffeur?
  • Would you rather have free vacations for the rest of your life or free meals?
  • Would you rather give up music or movies/TV?

My 3 Favorite Things About You

If Would You Rather runs the risk of being a little too fiery for your family and friends, My 3 Favorite Things About You is a good-hearted alternative for bringing some warmth to the dinner table. While other questions, conversation-starters, and games serve as effective icebreakers and talking points, this one is simply about spreading the love.


Make playtime out of genuine positivity with this self-explanatory game: in turns, ask dinner guests to share their three favorite things about one another. The genius of using this as a holiday game is that it negates the anxiety hosts and guests feel at the prospect of controversy — instead, simply lifting each other’s spirits by sharing what you think makes one another special. And who isn’t looking to finish the year feeling a little uplifted?

From faculty and staff to students and graduates, the Goodwin community forms a diverse family of learners, thinkers, doers, and changemakers. This holiday season, we wish joy, safety, happiness, and health to all the individuals that make Goodwin University a special place to find your path. Learn more about joining the Goodwin community today! Call 800-889-3282 or text 860-467-1511.