Conversation Starter Generator
“What's a rule you live by that nobody else seems to follow?”
Why ask it
Personal bylaws are wonderfully specific: never shop hungry, always return the cart, no email after nine. You get a value system in one sentence.
Some of what is in the deck
Prefer to read than to shuffle? These are the opening cards of each deck, each with its note and the set it came from.
Everyone
What's a rule you live by that nobody else seems to follow?
Why ask it
Personal bylaws are wonderfully specific: never shop hungry, always return the cart, no email after nine. You get a value system in one sentence.
What's something you were late to and now can't stop recommending?
Why ask it
Lets people be enthusiastic without pretending to be early adopters. It could be a show, a vegetable or stretching. Take the recommendation seriously and they'll light up.
What's the best thing you've eaten in the last week?
Why ask it
Recent and low-stakes, so nobody has to rank a lifetime of meals on the spot. The follow-up writes itself: where was it, and would they go back?
What's the last thing you learned to do from an online video?
Why ask it
Surfaces the practical side projects nobody mentions: fixing a faucet, cutting a mango, tying a tie at forty. Ask whether it actually worked.
What's something you're glad you did before you knew better?
Why ask it
Harder than it looks, because it asks for a risk and a verdict at once. The stories tend to be good: a move with no money, a car bought unseen, a job taken on a whim. Ask whether they'd do it again knowing what they know now.
What's an opinion about food you hold more firmly than is reasonable?
Why ask it
Low-stakes disagreement is good for a group, and nobody gets hurt arguing about raisins. Invite a rebuttal from someone else to pull the whole circle in.
What's something you own that you'd never trade for a newer one?
Why ask it
The object is a doorway to whoever gave it to them or where it has been. Ask how long they've had it, and what would have to happen for them to let it go.
What's a small thing you bought that turned out to be worth far more than it cost?
Why ask it
People enjoy evangelizing about a cheap object that fixed their mornings. Expect a vegetable peeler or a phone stand, and expect to leave with a shopping list.
Whose idea was it for you to come along today: yours or someone else's?
Why ask it
Gentler than asking what someone does for a living, and the answer shows who they know in the room. If they were talked into coming and so were you, say so. Handy at the door of any event where you know nobody.
With friends
If we'd met ten years earlier, do you think we would have been friends?
Why ask it
A playful way into how much each of you has changed. The honest answer is often no, and explaining why turns out affectionate, not insulting.
What's a favor you'd feel awkward asking me for, but wish you could?
Why ask it
Keep this for a close friend and a quiet moment. The answers tend to be small, a ride to the airport or a hard phone call, and saying them aloud removes the awkwardness.
What's one way you've changed since we met that you think I haven't noticed?
Why ask it
Long friendships run on outdated versions of each other. This updates the file, and it tells you what they've been working on privately.
On a date
What's a deal-breaker you used to have that now seems silly?
Why ask it
Lets them talk about dating without talking about exes. It shows whether their standards have been examined or merely collected.
Where do you end up at a party: the kitchen, the dance floor, or talking to the dog?
Why ask it
Sorts introvert from extrovert without using either word. Dog people will identify themselves at once, which is also worth knowing early.
What's something you're nerdy about that doesn't usually come up on a first date?
Why ask it
Gives explicit permission to go on about trains, fonts or sourdough. People relax when they stop performing and start explaining, and relaxed is what you want.
With family
Who in the family are you most like, and do you take that as a compliment?
Why ask it
Whether it's a compliment is what makes this interesting. People will often name a trait they share with a parent that they've never said out loud before.
What's a family photo you love, and what was happening just outside the frame?
Why ask it
What the camera missed is the real subject: the argument before the shutter, who was crying, who was holding the camera. Best asked with the photo on hand.
What were you scared of as a kid, and when did it stop?
Why ask it
Reassuring for any child at the table to hear an adult admit to the dark or the basement. The second half is the comforting part: it did stop.
At work
When and where do you do your best thinking?
Why ask it
Practical intelligence for anyone who schedules meetings. If half the team says early morning, you've just learned when to leave them alone.
Which item on your to-do list this week would you pick first if the order were up to you?
Why ask it
Finds the work someone likes without asking them to perform enthusiasm. If the honest answer is none of it, that's worth a private follow-up, not a public one.
If you had to switch careers next year, what's the realistic pick and what's the fantasy one?
Why ask it
Two answers keep it safe: nobody sounds like they're resigning. The fantasy pick, baker, park ranger, tells you what the current job is missing.
For couples
If we had a spare room to do anything with, what would you turn it into?
Why ask it
A small, playful way into what each of you lacks space for: a workshop, a library, a room with a door that shuts. Sketch it on a napkin if you like.
What did you do to impress me in our first months that you'd never bother with now?
Why ask it
Ironed shirts, a suspiciously tidy apartment, enthusiasm for a band they couldn't name a song by. Confessing the early performance is funny, and it doubles as a compliment to how comfortable you've both become.
What did I do this week that you noticed but didn't mention?
Why ask it
Appreciation often goes unsaid because the moment passes. This gives it a second chance. Be warned that the answer may also be the wet towel.
With kids
If you wrote a book, what would it be about and who would be the hero?
Why ask it
The hero is often the child in light disguise, with a better name and a horse. Offer to write down the first page while they dictate, and you may get a second.
If you dug up a treasure chest in the yard, what would you hope was inside?
Why ask it
Gold comes first. Asking 'and what else?' turns up better things, such as a map, a puppy or a letter from a pirate. Say what you would hope for, and whether you would share it.
If you could put up a statue of anyone or anything in the middle of town, what would it be?
Why ask it
A child's idea of who deserves a statue is worth hearing: a grandparent, the dog, the crossing guard. Ask what the plaque underneath would say.
With teens
What are you trying to get better at right now, just for yourself?
Why ask it
"Just for yourself" rules out the goals adults have set for them. Note whether the answer is a skill or a trait, since wanting to be less anxious or more organized is a different conversation from wanting a better free throw.
How is your friend group different from a year ago?
Why ask it
Friendships reshuffle a lot in these years and adults tend to find out months later. A plain factual question lets them report a drift or a falling-out without having to call it a loss. Ask who they miss.
How have you been sleeping lately?
Why ask it
Easier to answer than a question about mood, and it often carries the same news: sleep tends to slip when a teenager is worried, overloaded or on a phone late. If it has been poor for weeks, raise it with their doctor before it becomes an argument about bedtimes.
How to use a conversation starter
Choose who you are talking to, deal a card, and ask it the way you would ask anything: looking at the person, not the phone. Then stay with the answer. One follow-up question does more than three new cards.
If a card is wrong for the moment, deal another. Nobody needs to know there was a first one.
Three habits that make any starter work
- Answer it yourselfGo first if the other person hesitates. A question lands better when it comes with an answer attached.
- Follow the detailPick the most specific thing they said and ask about that. The note under each card often suggests where to go.
- Let silence do some workGive a new question a few seconds before you rescue it.
Three ways to use it
- One card at dinnerDeal a single card when everyone has sat down and let it run as long as it runs.
- Around the tableEveryone answers the same card in turn, and the person who dealt it goes last.
- In your pocketBefore a party, a date or a one-to-one, deal a few, copy the two you like and keep them for when the talk slows.
A deck for the company you are in
- EveryoneQuestions that work in any company, from a relative to someone you met an hour ago. Start here when no other deck fits.
- With friends, on a date, with family, at workFrom the same set, the questions written for that company.
- For couplesFor two people who already know each other well: everyday check-ins, memories, dreams and a few hard ones for a calm evening.
- With kids and with teensQuestions for a parent, relative or teacher to ask a child or a teenager, each with a note on what to listen for.
The sets behind it
Nothing is written on the fly. Every card comes from one of these question sets, and each set has the whole list in an order that builds.