In the first few weeks, when everything is still light
Early on, small and specific beats big and meaningful. These are the ones you can ask while the coffee is still being made.
- The barista is about to call your name. What’s your usual order, and does it change with the weather?
- Your alarm goes off at 7 tomorrow. What song would you pick to wake up to, if you could pick anything?
- Someone asks how your weekend was. What was the best hour of your last one?
- You’re showing someone your street. Which corner or shop would you point out first?
- A friend’s birthday is coming up. What’s a gift you gave that people still talk about?
- It’s Sunday evening. What small ritual makes the week feel ready to start?
- A guest opens your fridge. What’s always in there?
- The two friend groups are about to meet for the first time. What would your friends say you’re best at?
- A free Saturday opens up. What do you do with the first hour?
- You scroll through your camera roll. What’s the most recent photo you’re glad you took?
Sam: I asked Anna “What are your hobbies?” on our second date. She looked at me like I was a form. Next time I asked what she did last Saturday morning, and we talked for an hour.
Over dinner, when nobody is looking at a phone
Dinner is the easiest place for a follow-up question, because the food gives you both something to do with your hands. If you still need a place for that dinner, there’s a deck of first date ideas.
- You’re reading the menu. If any restaurant could make one dish from your childhood, what would you order?
- A friend has had a terrible week and is coming over. What do you cook for them?
- The check is on its way. What’s the best meal you’ve ever eaten, and where were you sitting?
- The dessert menu arrives. What’s the last dessert you finished a whole plate of?
- A candle flickers on the table. What’s a smell that takes you straight back to a specific place?
- Someone’s visiting from out of town. Where do you take them?
- The table next to you is celebrating loudly. What’s the best party you’ve ever been to?
- The plates are cleared but nobody wants to leave. What was your first job, and what did it teach you about people?
- Friends come up. What does a normal night out with your closest friends look like?
- Someone brings up travel. Which trip would you repeat tomorrow, exactly as it went?
Anna: On our third dinner, Sam said “So, five-year plan?” and I nearly choked. He laughed, tried again with “What did you eat as a kid on your birthday?” and I talked until the dessert melted.
On a long drive or a train ride
The window gives you something to look at, so questions feel less direct. Nobody has to hold eye contact while they think.
- A quiet stretch of highway. What was the first album you played until it wore out?
- A song comes on that you haven’t heard in years. Which trip or summer does it belong to?
- You pass a town you’ve never stopped in. What would you hope to find there?
- The sun is going down and the car is warm. What are you looking forward to in the next three months?
- You pull into a gas station. What’s your road-trip snack that nobody else approves of?
- You pass a school with kids outside. What was the best part of your school day?
- A road sign points to somewhere you’ve always meant to see. Where is it?
- The radio fades into static. If you got a month off starting tomorrow, what’s the first thing you’d do?
- You pass a field of cows. What animal would you secretly love to own?
- Traffic stops completely. What’s the longest you’ve ever waited for something, and was it worth it?
Late at night over text
These are built for one or two messages, so nobody has to write an essay at 11 p.m. (More lists like this one live in our articles.)
- It’s 11 p.m. and they say they’re still up. What are you watching or reading right now?
- They send a photo of their dinner. What do you cook when it’s just you?
- They’re under a blanket on the couch. What’s your comfort movie, the one you can watch half asleep?
- They mention a long day. What was the best part of yours?
- It’s too late to call. What song has been on repeat this week?
- They send a photo of the street outside. What’s the view from your window?
- They send a selfie with a new haircut. What’s the best haircut you ever had, and the worst?
- It’s late and tomorrow is Monday. What gets you out of bed in the morning?
- They ask what’s next. What’s the plan for this week you’re most looking forward to?
- It’s goodnight time. What’s the last thing you do before you fall asleep?
Sam: I texted Anna “Tell me about your childhood.” Four minutes of silence. Then I sent “What’s the street you grew up on like?” and got a paragraph with a dog in it.
On a walk, when you want to know how they grew up
Walking side by side makes it easy to ask about the past. Whatever you pass can start the question.
- You pass a playground. What did you do after school every day when you were eight?
- A kid wobbles by on a bike. Who taught you to ride, and where?
- You walk past a bakery. What did your family eat on Sundays?
- You pass a front yard with a swing. What did the house you grew up in look like from the street?
- A dog pulls on its leash. Did your family have a pet, and who actually looked after it?
- A school bell rings in the distance. Which teacher do you still remember by name?
- It’s a warm summer evening. Where did you spend your summers as a kid?
- Someone’s family is eating on a porch. Who in your family could make the whole table laugh?
- You pass a corner store. What’s the first thing you bought with your own money?
- Two kids are arguing over a toy. What was the typical argument at your house growing up, and who usually won?
When you want to hear what they actually care about
People can tell when you’re actually listening. These questions work best when you’ve already asked a few lighter ones and you’re curious about more than the surface.
- A friend asks what you’ve been into lately. What’s the rabbit hole you’ve gone down this month?
- Someone hands you a free year. What project would you start?
- A friend calls in a crisis. What do you do in the first ten minutes?
- You’re signing up to volunteer for one afternoon. What cause do you pick?
- A coworker is leaving the team. What would you want them to say about the way you worked?
- You lose track of time doing something. What is it?
- A big decision lands on your desk. Who do you call first, and do you want advice or just a listener?
- You’re asked to give a toast at a friend’s wedding. What do you say about them?
- Someone hands you a thousand dollars you have to spend on other people. Who gets it?
- You close your eyes at the end of a really good day. What made it good?
Anna: The best answer I’ve gotten was to “What’s the rabbit hole you’ve gone down this month?” Sam spent twenty minutes on how bridges are inspected. I’ve never seen anyone so happy about rust.
A little later, once there is some trust
Some topics land better after a few weeks. If a question feels like too much, “ask me later” is a full answer, and it goes both ways.
- You’ve spent a few weekends together and had your first small disagreement. Do you like to talk it out right away or cool off first?
- You’re planning a trip together. What do you need from a trip: movement or rest?
- They’re about to meet your closest friends. What do you hope those friends notice?
- They bring up an ex in passing. What’s one thing you took from your last relationship and are glad to keep?
- A bonus lands in your account. What did you learn about money growing up, and what do you still do because of it?
- A friend shows up with a newborn. Do you picture kids someday, and what does that picture look like?
- You’ve both been busy and haven’t talked in a day. How much space feels right to you?
- A holiday is coming up. How do you picture splitting time between families?
- You’re thinking about giving them a spare key to your place. What would that key mean to you, and when does it feel right?
- You’re a few months in. What would you like to be true of the two of you by next summer?
If you’d like a longer set to take turns with later, the couples deck has one you can open on a single phone.