Dinner Party Conversation Starters That Don’t Feel Like an Icebreaker

For those of us who love having people over but occasionally forget how to behave once they arrive.

I am an introvert who likes having people over, which occasionally feels like a fairly significant design flaw.

I genuinely love gathering people around a table. I love the food, the candles, the moment when everyone finally sits down and the evening starts to feel like an evening.

What I do not love is mingling.

Left without a specific assignment, I tend to choose one person and quietly decide that we are going to be together for the foreseeable future.

Or—and this is where hosting comes in handy—I suddenly remember that there are very pressing matters in the kitchen.

Is the oven fine?

Probably.

Do I need to check it again?

Absolutely.

Someone has to make all of this happen.

The funny thing is, I don’t think I’m particularly unusual.

Not everyone walks into a room full of people and thinks, Fantastic. Twenty conversations I could start.

Some of us need a minute. Some of us attach ourselves to the person we know best. Some become extremely interested in helping with the dishes.

And then there is the opposite problem.

We’ve all been at a dinner with one or two wonderfully funny, wonderfully enthusiastic people who, without meaning to, become the evening’s unofficial podcast hosts.

Nobody is doing anything wrong.

The room just needs a little help.

This is why I’ve changed my mind about conversation cards

There is a particular kind of party game that makes perfectly normal adults suddenly look as though they are being held against their will.

You know the kind.

Everyone is having a perfectly nice time and then someone announces:

“Okay! I thought it would be fun if we went around the table…”

No.

We were doing so well.

I don’t want to reveal my greatest fear to Susan’s new boyfriend before the salad has been cleared.

But I do think the right question at the right moment can completely change an evening.

Because good conversation starters aren’t really about preventing silence.

They’re about giving everyone a way into the conversation.

The quieter person gets an opening.

The person who has been carrying the conversation gets to listen.

The host doesn’t have to keep scanning the table thinking, Is everyone having fun? Should I ask something? Should I go check the oven again?

And every once in a while, somebody tells a story you’ve somehow never heard before.

That’s the good stuff.

Start with something everyone can answer

Early in the evening, nobody needs to explain the defining experience that shaped who they are today.

We have appetizers.

Start easy.

What is something you are weirdly particular about?

What’s a completely unnecessary purchase that you have never regretted?

What food could everyone else stop pretending is good?

What’s something you genuinely love that you’re slightly embarrassed to admit you love?

The goal isn’t profundity.

The goal is getting six different personalities into the same conversation.

Then give people something worth telling a story about

The best questions don’t produce answers.

They produce stories.

There’s a difference between:

Where did you go on your last vacation?

and:

What’s the funniest thing that’s ever gone wrong on a trip?

One gets you a destination.

The other gets you the story about the rental car, the missed ferry and somebody’s mother refusing to leave a restaurant.

Try:

What’s a small lie you told that became much harder to get out of than expected?

I happen to have a banana cream pie story for this one.

What’s the most ridiculous argument you’ve ever been completely convinced you were right about?

What’s something you were absolutely certain you’d hate—and then loved?

What’s the strangest thing you’ve ever done because you didn’t want to be rude?

Those are the questions that make people say:

“Wait. I have one.”

That’s what you’re looking for.

Funny is usually better than impressive

This is where I think hosting can get unnecessarily serious.

We put people in a beautiful room, serve them good food and then somehow decide the conversation needs to be equally sophisticated.

It doesn’t.

Sometimes the thing everyone remembers is finding out that the most polished person at the table once accidentally attended the wrong wedding for twenty minutes.

Give people permission to be funny.

What is the pettiest hill you are willing to die on?

What everyday task are you embarrassingly bad at?

If your family gave out awards, what would yours be?

What is your most irrational household rule?

What’s something you believed for an embarrassingly long time?

Nobody has to give a brilliant answer.

That’s rather the point.

Save the better questions for later

Once dinner is underway and everybody has settled in, you can go somewhere a little more interesting.

Not corporate retreat interesting.

Human interesting.

What are you looking forward to right now?

What’s something you’ve gotten better at caring less about?

What’s one ordinary thing in your life that you hope never changes?

Who makes your life more fun?

What’s something you wish we all did more often?

You don’t need ten of these.

You may only need one.

A good question has a way of disappearing once the conversation takes over.

Let it.

The card has done its job.

The host does not need another job

This may be the part I care about most.

We’ve somehow turned hosting into an enormous collection of responsibilities.

Make the food.

Clean the house.

Set the table.

Remember who doesn’t eat what.

Make the playlist.

Keep the drinks filled.

Introduce everyone.

Keep dinner moving.

Make sure people are having fun.

Rescue awkward silences.

Include the quieter guest.

And apparently remain charming and relaxed while doing all of it.

No wonder I keep finding urgent things to do in the kitchen.

A little structure doesn’t make an evening less natural.

Sometimes it makes it more natural because nobody has to work quite so hard to make the night happen.

It’s also one of the reasons we build conversation cards into The Good Evening.

Not because your friends need instructions for speaking to one another.

Because the host shouldn’t have to be responsible for the chicken and the emotional momentum of the room.

We planned that part too.

And if all else fails, you can always check the oven.

Again.