10 Conversation Starters for Family Dinners During the Holidays

by | Nov 20, 2023 | Family | 27 comments

Sheila here!

This is a post from Rebecca from a few years ago, and with the holiday season approaching, I thought it would be a good idea to revisit it!

Ever wanted to make family dinners more meaningful?

And I’ve got to say, if you want meaningful conversations, you should meet my Nana.

My Nana (Sheila’s mother) loves to get people to talk.

And not small-talk or chit-chat–I mean actually talk. Like about what makes you feel true joy in your soul, or what disappointments have shaped who you are as a person. I don’t think anyone can sit down for more than an hour with my Nana and not learn something about themselves.

Last Christmas for the Gregoire side (my dad’s side of the family) we passed a basket with questions my Nana had written on little slips of paper. Nana lives with Mom and Dad, so she joined us for Dad’s side, even though she’s not on Dad’s side. And she really did transform our family traditions.

My cousins were confused and a bit hesitant at first, but it was really fun! It gave us easy conversation, we learned more about each other, and it presented natural opportunities to share funny stories from the past year.

Once we were done, the cousins who were least excited at the beginning started passing around the basket again for a second round.

As a result, we left that Christmas dinner feeling much more connected as a group. Family events are often one of the only times we gather with extended relatives in a year, but we so rarely actually talk about how we’re really doing, what’s actually going on, beyond the brief “how’s work, how are the kids” conversations.

But first, there are a few general principles that can make having real conversations as a family easier:

First, serve the food at the table instead of buffet-style in the kitchen.

This means that during the meal, everyone is sitting around the table together. You don’t have people getting up in the middle to refill their plate, you don’t have a line of people trying to get at the mashed potatoes. People all arrive at the table at the same time and leave at the same time, which makes conversation much easier.

Second, more tables with fewer people can be better than one table with everyone.

If you’ve got so many people that having a conversation with everyone at once is difficult, consider splitting up the tables. In our family, last year we had a “grown ups” table (even though everyone in our family is over 18 now except for the newest addition) and the “cousins” table, where aunt Carrie indignantly snuck into anyway, because there was no way she was going to miss out on all the fun. We’ll likely switch it up year after year so we all have a chance to sit with each other, but it made conversation so much easier since you were only talking with 6-10 other people instead of the entire family at once.

Third, it’s best to introduce the questions after everyone has served themselves but while they are still eating.

Trying to start a great conversation amidst the “pass the peas” and “where is the stuffing” often just leads to frustration. Wait for people to have their food, and then get started on the conversation! Plus, then it’s easier to ensure that only one person talks at a time since everyone else is busy eating.

Fourth, do the questions in one of two ways

Either have everyone answer the same one or two questions (you can choose them below) or put a bunch of different questions in a basket and pass the basket around. If you’re going to use the basket, here’s a handy tip: Give everyone one “out”. If they pick a question they just don’t want to answer, they’re allowed to draw another one.

So here are 10 conversation starter ideas to help you and your family not only meet up this holiday season, but really connect.

1. Share something you’re proud of from this last year

This isn’t just about the obvious victories, too–not just the promotions, the successes, or the awards. Maybe this year you finally read that book you’ve had on the back burner for forever. Maybe you spent more time with family than you did last year. Maybe you finally got that dog of yours to come back when called. No pressure to think of your most impressive accomplishment–just what you’re proud of. Let’s celebrate the little victories, too!

2. Share something you’re disappointed with in the past year

This one sounds like a bit of a downer, but it was actually one of the best questions we had, because people really opened up! And you often learn more when you share disappointments about what people are actually feeling.

3. Share something you want to achieve in the coming year

And then make plans to keep each other accountable or encourage each other in the journey! Are there a few of you who want to become more active? Create a group text where you can plan times to do an active outing together once a month and keep each other on track in between!

4. Share something new that you learned this year

I know what  my husband Connor’s answer would be! He’s so proud that he figured out how to fix a sink so that we didn’t have to call a plumber!

5. When was the last time you laughed so hard your sides hurt, and when was he last time you cried?

This is similar to the high-low questions but much more story-based. You may be surprised by what you hear–often it’s the people we least expect who have the funniest, most side-splitting stories!

6. Ask everyone to come with a book/movie/TV show recommendation

Why do they like that book so much? What makes that movie so important to them? And as a bonus, now you’ll have a list of books, movies, or TV shows to watch so that when you’re bored on a week night you’ll have lots of entertainment options that will give you something to discuss with the other members of your family–even the ones who are sometimes more difficult to connect with. If you’ve read your incredibly introverted uncle’s favorite book, that can lead to some great conversation!

7. Play “would you rather”

Would Uncle Randy rather live in a castle but never see another person for his entire life, or in a small apartment with 30 other people? Would Grandma rather live in the arctic where it’s too cold or in a desert where it’s too hot? This is an easy game for family members who aren’t as chatty since the options are presented before them and all they have to do is pick!

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8. Discuss where you saw God move this last year, or where you need prayer this year

Often we don’t ever take time to really sit down and ask ourselves where we saw God moving and so we assume that we didn’t see Him at all. But actually thinking about it and looking back can bring the perspective needed to see where He was moving all along. If your family is religious, this can be a great way to challenge each other to look for signs of God’s presence and provision over the last year and ask for some prayer for the year ahead.

9. Tell a story about someone you admire

Whether it’s a public figure, a friend, or even a character in a book, each person explains why they chose that person and what about them makes them so admirable. You can learn a lot about your family members by learning who they look up to!

If your family is comfortable with it, change this so that each person says something they admire about the person to their right, with a specific example. It can be an amazing way to encourage each other and bless the members of your family.

10. Share your high-lows for the year

Everyone around the table shares what the high- and low-points of this year were. It may sound a bit like a downer to talk about low points, but it can be quite nice to share when we are hurting and family support can be a huge benefit during struggles, too. By doing this, we learn to celebrate with each other’s victories and also help carry each other’s burdens–and that’s a perfect picture of family.


BONUS: Ask everyone to bring a photo of themselves at the same age

And share a memory from that year. Everyone brings a photo at a specific age (say age 9) and you’ll hear about the horrific camp counselors your aunt had that summer, about how your grandfather joined a band even though no one could play any real instruments, and how your little sister fell into her friend’s pool fully clothed and was too embarrassed to go back for 8 months.


What are some of your suggestions for getting families to talk around the dinner table this Thanksgiving or Christmas? Share them in the comments below! 

Written by

Sheila Wray Gregoire


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Sheila Wray Gregoire

Author at Bare Marriage

Sheila is determined to help Christians find biblical, healthy, evidence-based help for their marriages. And in doing so, she's turning the evangelical world on its head, challenging many of the toxic teachings, especially in her newest book The Great Sex Rescue. She’s an award-winning author of 8 books and a sought-after speaker. With her humorous, no-nonsense approach, Sheila works with her husband Keith and daughter Rebecca to create podcasts and courses to help couples find true intimacy. Plus she knits. All the time. ENTJ, straight 8

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  1. Ina

    I love this! We had Thanksgiving a month ago but now I kind of want to invite people over just to try these out! Your Nana sounds a lot like my mother. Random strangers will just pour out their life stories to her on the regular. I am not gifted with that… for which my introverted heart is a bit grateful.

    • Shari Smith

      I hope you get a chance to try these questions out!

  2. Chris

    I like the option to pass on a question but it also might be fun to be able to assign the question you draw to someone else. Just a thought.

    • Lisa Johns

      That sounds fun, lol!

      • S

        Its funny how some would see this as so much fun and others (me) think having someone assign me a question is enough to make me not be at the dinner table at all! I am old and wise enough now to just say no thank you firmly and without apology when I am not comfortable with a situation, but I would task everyone who thinks ice breakers like these are fun for all, to make sure everyone has a way to say no without pressure, because some people would rather not come than be pressured into sharing when they don’t want to.

        • Shari Smith

          ohhh yess! Great point. As an introvert, ice breakers can feel super challenging if I’m not given an easy way out.

        • Fiona

          Yes, I think some lighter, fun, less intrusive questions would be better. I would never expect to reveal so much at a dinner party. Nope, this would have me running for the hills and very reluctant to return.

  3. Eve Sumrall

    Cant wait to try this it sounds like you are getting more than conversations with your family

  4. S

    This sounds like an introverts nightmare, guess what we are going to ask personal questions and you can only opt out once, I think I would panic a bit at a dinner like this! I would offer the basket of questions to anyone who choses to participate and let people opt out all together if they would rather not be expected to share, and just want to be present to enjoy the company. We do buffet style because the table is just not big enough to put all the dishes on it, and you will still have conversation breaks while asked to please pass the stuffing mid meal, or hand people your dirty plate if the stuffing dish is to hot to pass is kind of yuck.

    • Lisa Johns

      Yes, allowing people to opt out is probably a necessity. But still having them there to be able to listen would be fun for them!

  5. Jo R

    If one is with family and friends, wouldn’t these topics be part and parcel of general life and conversations all year long?

    I’m going to have to agree with S as well, about the poor introverts in the crowd. The introverts probably used up a lot of their stamina and courage and people time just to show up!

    • Nessie

      Jo R- my experience has been- with friends, yes, these topics are part of life, but with our families, no, even these questions are too “personal” for most of our family members, and it isn’t due to introversion. We have many family members that are really good at sweeping… everything under the rug, lol. For others, answering anything like this is too vulnerable and/or will be used to manipulate.

      I wonder if there could be introvert and extrovert tables? Each introvert table could seat 2, and all the extroverts lump at one table. As an introvert, that’d usually be my preference though I do try to be more social for special occasions.

    • Angharad

      Introvert here, and while I can see this is a great idea for extrovert families, it would be 100% guaranteed way to make sure I never, ever gain turned up at any family gathering!

      • Greta

        Completely agree it would run off way more people than it would help. Maybe a good idea for Sheila’s family but definitely not for my family and sounds like not for a lot of other people’s families either.

        It reminds me of a scene in the movie called “Couples Retreat” from a few years ago where four couples go to a tropical island vacation but have to mix in therapy sessions with fun beach stuff. Mr. Vince Vaughn’s character’s marriage is going fine but the therapist stirs up unnecessary conflict. He’s talking to his friend played by Jason Bateman that brought all the couples on the trip and says “thanks a lot buddy for bringing me to problem island!”. 😆😆😆

        Really funny movie if anyone wants a good laugh over the holidays.

    • Shari Smith

      I think it can depend on the relationship. I don’t see my extended family very much, so we don’t typically have these kinds of conversations. Ice breakers like these could be a fun way for people to dig a little deeper!

  6. Constant thoughts

    This sounds fascinating. But, as others said, it opens up a lot of vulnerability. I can actually hear a family member responding to someone’s answer with…”Well, that’s stupid. Why would you do that?” I can actually hear the voice. And I can see the downcast face on the person who was trying to share. The thing is, the person saying harmful things doesn’t even realize what they are doing.

    It’s enlightening for me to realize this. It explains some of my anxiety.

    Maybe it would work as a list of conversation starters. And if someone wants to volunteer, that might work. I suspect members of my family may feel too vulnerable to answer. This makes me wonder about generational trauma. It gets perpetuated even when we don’t realize we are doing it.

    I would really love to have some of these conversations with my family. I would love to know what is going on. I would love to know history. I would love to connect more deeply.

  7. Nessie

    Anyone have suggestions for those who won’t be with family for holidays for various reasons? Most of our family is very toxic and we are not invited to the “family” gatherings. We’ve had to come up with alternative holidays.

    Sometimes we host others who have nowhere to go. This has been eye-opening at times as we have had people from other countries who have never experienced an American Thanksgiving (or Christmas) nor our traditions. It really helps to see how others may experience what is “normal” for us e.g. if you’re used to making casseroles, it’s interesting trying to explain them to someone who has never remotely heard of them, haha. It also helps you think about the “why” behind some traditions.

    I’ve heard of many helping at soup kitchens, etc., but occasionally they get so full of volunteers they’ve had to turn them away. So I’m curious… how do others spend holidays who aren’t with family?

    • Jo R

      We had been sort of adopted by different families at our church when we lived halfway across the country from actual family. We were regularly invited not only for the big holidays, but even for Memorial Day cookouts and whatnot.

      When we were first married, we made a conscious decision to NOT travel to family for the first twelve months for the various holidays. Why? Well, we were poor! We also didn’t have enough vacation at work to take enough time to drive halfway across the country. Also, we expected to have several kids and thought that I’d be pregnant or nursing at least once at Thanksgiving and/or Christmas, so why should I subject myself to 1000 miles of driving under those circumstances? (I loathe flying in the best of circumstances, so there was zero chance of me flying with little kids.)

      We thought that not traveling that first year would help make it a treat in those years we did travel, rather than having to hear “But you’ve always come home!” every year in perpetuity. 🙄 (We felt so strongly about this that we’ve always counseled newly engaged couples to do likewise.)

      We also planned to develop our own traditions, and “always traveling to family” was not in the least on the radar as one of those potential traditions.

    • Angharad

      Hosting others who don’t have family to go to is brilliant! If you can’t do this for any reason, I would suggest throwing the ‘rulebook’ out and starting totally new holiday traditions – the problem with hanging on to the things you traditionally do when you don’t have family to do them with any more is that they can be a constant reminder of what is missing (although I know some people do find keeping everything the same is helpful – it just doesn’t work for me!)

      Plan ahead. Think of some foods you would really love to eat and some things you would really love to do – walks, board games, day trips out – and save them all up for the holiday – instead of looking at what you wont’ have for the holiday, look at it as ‘yay! we have this time to do all the stuff we want to do and don’t get time for normally’. I think it also helps to be realistic about the alternative – it’s easy to get starry-eyed about the ‘traditional’ holiday gathering, but if your family is not like that, the reality is that you are not going to be experiencing that ‘happy family vibe’ anyway – sometimes, just reminding yourself that ‘at least we don’t have to have dinner with [insert name of toxic family member]’ can be enough to make you feel better about spending the holidays on your own! We have to host my incredibly toxic mother for just about every family holiday – I’m already dreading Christmas – and while we missed a lot about our Christmas during Covid, it was a huge relief not to have to have her with us.

      • Nessie

        I really like the idea of saving up special activities for the day to make it special!

        The years we have hosted others with no one else to spend it with were great. I simply struggle in finding those people to invite. I’m not outgoing enough to really find out who they are without feeling like I’m being nosy.

        I think the hardest part about not being with the family is the lies that are told about us to the children involved. I hear you about the relief quarantine gave!

        I’ve been working on reframing how to think about things like holidays but thanks for the reminder. 🙂

    • Shari Smith

      oh good question!!

      When I cut contact with my family, I would seek to spend holidays with friends instead. So I had a lot of friendsgiving celebrations. One of my best friend’s birthday is on Christmas Day, sometimes we’ve spent the day celebrating her instead. This Christmas, my husband and I are taking a trip.

      I think anything that can remind you that you have love, happiness, and community outside of your estranged family can be very healing and restorative.

  8. Constant thoughts

    I am finding the comments on this are fascinating. This article has been a conversation starter in more ways than one.

    For some this question game would be wonderful. For others it may not work. And others still may not have family to gather with. We all have unique circumstances. And it’s nice to be able to discuss those circumstances. It allows us to understand others a little bit better. Understanding is never a bad thing.

    Thank you for the article and thanks to everyone who commented.

    • Shari Smith

      I agree! There are always nuances and differences. Listening with empathy is a great way to understand one another.

  9. NL

    Yeah. I was thinking as I read this- WAY too much vulnerability. Not something we would be up for in our family. My mother would think it was great, but we would be guarding our answers and feeling manipulated.

  10. JoB

    My family would also not be a good match for more personal questions, but we have done simple get-to-know you better questions like “what’s your favorite color” (seems silly, but I didn’t know my brother likes green!), favorite season/month/holiday, favorite animal or plant, favorite snack. Talking about pets/animals will sometimes be a glimpse at the heart of people with very gruff or avoidant personalities. Having a little conversational structure is good…Anything to keep politics or personal grievances off the table!!! 😅

    • Nessie

      That’s a great point. Having at least some prepared structure of conversation ready, whether it gets used or not, can help to redirect if conversation goes in a more heated direction. 😀

  11. Susan Shuffield

    It surprises me and makes me sad to hear that these types of conversations are not happening on the regular with family and friends, and that so many would feel pressured or uncomfortable having them (maybe just because of the presentation?). I think as a society, we have lost the art of conversation and, with it, the associated subsurface connections with the people in our lives. We are deeply social beings, and people used to have margin in their lives to talk to people. We just don’t prioritize that anymore. To combat this, our family has slowed down life as much as possible, and sits down to dinner together around the table every night. On the whole (at dinner and throughout our day), we aim to discuss ideas and stories instead of things (like the newest iphone that someone wants) and/or gossip. I have heard that making a coffee date once a week with someone you would like be closer with is also a good idea. I hope everyone is able to find a way to better connect with those they love. We need each other. We need support and connection.


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