Why Do Thanksgiving Conversations Stay So Shallow? 40 Thanksgiving Questions That Go Deeper

Thanksgiving questions that go past small talk: 40 prompts for family and Friendsgiving, plus why deeper talk goes better than expected.

Gizella Nagyne Palinkas

10/20/20268 min read

Short answer: most Thanksgiving conversations stay shallow because we expect deeper talk to feel more awkward than it actually does — and we assume other people care less about our answers than they really do. Below are 40 Thanksgiving questions, sorted from easy openers to genuinely deep ones, so you can raise the level one step at a time instead of jumping straight in.

The 40 Thanksgiving questions (start at the top, move down when it feels right)

Easy openers — anyone can answer these

  1. What's one dish on this table you'd be sad to lose from the tradition?

  2. What was the best thing you ate this year that wasn't at a restaurant?

  3. What's a small thing that made this autumn better than you expected?

  4. If this year had a title, what would it be?

  5. What's something you learned this year that surprised you?

  6. Which Thanksgiving from the past do you remember most clearly — and why that one?

  7. What's a tradition you'd like to start, even a silly one?

  8. What's the most useful thing someone taught you without meaning to?

  9. What song, book or show got you through a hard week this year?

  10. Who in your life always makes a room easier to be in?

One step deeper — about people and memories

  1. Who taught you how to cook something — and what else did you learn from them?

  2. What's a family story you've heard so often you could tell it yourself?

  3. What's something an older relative did that you only understood later?

  4. Who would you thank today if you knew they'd actually hear it?

  5. What's a kindness from a stranger you still remember?

  6. What did you think adulthood would feel like, and how close was it?

  7. What's a place that feels like home even though you don't live there?

  8. What's a mistake you made that turned out to matter less than you feared?

  9. What do you hope people say about this year when they look back?

  10. Which friendship has changed the most since you were younger?

Deeper — gratitude, change and what matters

  1. For what in your life do you feel most grateful right now?

  2. What's something you're grateful for that you didn't choose?

  3. What changed your mind about something important this year?

  4. What's something hard you got through that nobody at this table knows about? (Answer only if you want to.)

  5. What do you wish you'd been told at the age your youngest relative is now?

  6. What does a good life look like to you these days — and has that changed?

  7. When did you last feel really proud of yourself?

  8. What's a value you got from this family that you've kept — and one you've let go?

  9. If you could ask someone who's no longer here one question, what would it be?

  10. What are you quietly hoping for next year?

Questions for Friendsgiving (chosen family, mixed groups)

  1. How did you meet the person who invited you here?

  2. What's a friendship that started in an unlikely way?

  3. What's a "found family" tradition you'd keep forever?

  4. What's something you've only felt comfortable saying among friends?

  5. Who in this room has helped you without making a big deal of it?

  6. What's the best advice you've had from someone your own age?

  7. What would your ten-years-younger self think of this table?

  8. What's a place you'd love us all to go together one day?

  9. What's one thing you'd like this group to know about you that we probably don't?

  10. What do you want to remember about tonight?

How to use them: pick one from the first block for the start of the meal, one from the second once plates are full, and only reach the deeper blocks if the table is warming up. A question jar — strips of paper anyone can draw from — takes the pressure off any one person having to "start something", which is why it works well as one of the low-effort Friendsgiving ideas that isn't about food.

Why our conversations stay shallow in the first place

Researchers Michael Kardas, Amit Kumar and Nicholas Epley ran a series of experiments on exactly this question, published by the American Psychological Association in the Journal of Personality and Social Psychology. Their central finding: people systematically underestimate how much other people care about what they share, and so overestimate how awkward a deeper conversation will be.

Several results from the paper map directly onto a Thanksgiving table:

  • The expectation gap is bigger than the real gap. In one experiment with 89 pairs of graduate students, deep conversations did feel somewhat more awkward than shallow ones — but the difference participants expected was, in the authors' words, roughly four times larger than the difference they actually experienced.

  • It happens with people we know, too. In a field experiment with 200 pairs recruited in public parks, half the pairs were strangers and half were friends, spouses, partners or family. Both groups overestimated awkwardness and underestimated how much they would enjoy the conversation. The gap was smaller with close others — but it was still there.

  • People change their minds after trying it. In another experiment, 120 participants were asked before talking which kind of conversation they expected to prefer. On average they leaned towards the shallow one. After having both, they preferred the deep one (see the chart below).

  • We like hearing, but hesitate to reveal. In a pilot study, people who imagined only listening chose more intimate questions than people who imagined having to answer them. In other words, the reluctance is mostly about disclosing, not about curiosity.

The paper also cites earlier research suggesting that fewer than half of everyday conversations are substantive — which is why the small-talk default feels so normal.


One of the "deep" prompts used across several of these experiments was a gratitude question — "For what in your life do you feel most grateful?" — which is why question 21 above is borrowed from it. Thanksgiving gives you a ready-made excuse to ask it.

Why structured questions help: the "fast friends" idea

The question-ladder format above isn't new. In 1997, psychologist Arthur Aron and colleagues published a procedure in which pairs of strangers took turns answering 36 questions that became gradually more personal. Compared with pairs who answered 36 superficial questions, the closeness-question pairs reported a greater increase in feeling close. The key design choice was escalation and reciprocity: both people share, at a similar pace, starting light.

That's the logic behind sorting the 40 questions into four blocks. You don't need to reach question 40. Moving one block deeper than usual is the whole idea.

An everyday example

Picture a table where the conversation has looped through traffic, the weather and someone's new phone. One person asks, "What's a small thing that made this autumn better than you expected?" (question 3). A cousin mentions a neighbour who started leaving soup on her step after an operation. Someone else asks who taught her to make soup in the first place (question 11) — and now the table is telling stories about a grandmother. Nobody announced a "deep conversation". It moved one step at a time.

What this does not necessarily mean

  • It doesn't mean every relative wants to go deep. The research describes average tendencies across groups, not what any specific person at your table wants. Someone changing the subject is giving you information; take it.

  • It doesn't mean shallow talk is bad. In the studies, people also underestimated how connected they'd feel after ordinary conversations. Small talk does real work.

  • It doesn't mean pushing. The paper is about willingness to go a little deeper, not about extracting disclosures. Questions 24 and 39 are marked optional for a reason.

  • It isn't a fix for difficult family dynamics. These studies looked at conversations between people without major conflict. If a particular topic reliably causes hurt at your table, the questions above aren't designed to resolve that.

Practical things to try this Thanksgiving

  1. Answer first. Because the hesitation is mostly about revealing, going first with a short, honest answer lowers the cost for everyone else.

  2. Climb one block, not four. Start with an easy opener; move deeper only if people are leaning in.

  3. Use the jar. Put questions on paper and let people draw them — it shifts the "awkwardness" from a person to the jar.

  4. Give an exit. Saying "pass is always allowed" makes people more willing to answer, not less.

  5. Follow up, don't change topic. "What happened next?" keeps a story going better than a new question.

  6. Try it with the person next to you, not the whole table. In the park experiment, the conversations were between two people.

When professional help may be appropriate

If family gatherings regularly leave you feeling dread for days beforehand, or a particular relationship feels unsafe rather than just awkward, that's worth talking through with a counsellor or therapist. That's a pattern to understand, not a verdict on anybody — and it's beyond what a list of questions can help with.

Take the quiz

Not sure whether you're a small-talk keeper or a deep-question asker? Take the 2-minute quiz: What kind of Thanksgiving talker are you? It ends with which block of questions to start from.


FAQ

What are good Thanksgiving questions to ask family? Good Thanksgiving questions are easy to answer at first and invite a story rather than a yes or no. Try "Who taught you to cook something, and what else did you learn from them?" or "What's a family story you could tell yourself?" Start light and move deeper only if the table is warming up. Research on conversation suggests people expect deeper questions to feel more awkward than they actually do, so one step past small talk is usually welcome.

Why does deep conversation feel so awkward before it starts? Experiments by Kardas, Kumar and Epley found people underestimate how much others care about what they share, so they overestimate how awkward a deeper conversation will be. In one study, the awkwardness people expected from a deep conversation was much larger than the awkwardness they actually felt. The worry is front-loaded: it is strongest before you start talking.

Do these questions work for Friendsgiving? Yes — Friendsgiving groups often mix people who don't know each other well, which is exactly the situation the research studied. Questions about how people met, found-family traditions and who has helped whom work well. A question jar is one of the simplest Friendsgiving ideas that isn't about food, because nobody has to be the one who "starts" the deep talk.

What if someone doesn't want to answer? Let them pass, and make that rule clear before you start. The research describes average tendencies, not what any one person wants, and a relaxed "pass" option tends to make people more willing to join in later. Never push for a personal disclosure.

Are the 36 questions to fall in love the same as these? No. The 36 questions come from a 1997 study by Arthur Aron and colleagues on building closeness between strangers. The questions here are original, written for a Thanksgiving table, but they borrow the same principle: start light, escalate gradually, and let everyone share at a similar pace.

How many deep questions should I ask at one meal? There's no research-based number. A practical approach is one opener, one or two questions from the second block, and at most one deeper question — and only if the mood supports it. Mind Decoded's view is that the goal is one good conversation, not working through a list.

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