With the game (or the show) on, in the breaks
One screen, two people, and a game he actually cares about. Don’t open a conversation over a live play; wait for the timeout, the replay, the commercials. A one-word answer during a break is a fine answer, and the next break is four minutes away. If you’d rather play than talk, open the conversation deck and draw a card at random: 25 of them, for nights when you can’t be bothered to think one up. Or turn it into a quiz with how well do you know me questions.
- The commercials start with the score tied. Loser does the dishes: who wins this, and by how much?
- The slow-motion replay is on for the third time. Foul or clean, and would you have made that call?
- The camera finds a fan in full face paint. What’s the most you’ve ever done to your face or clothes for a team?
- It’s halftime and the chips are half gone. Which player from the other side would you steal for your team right now?
- The coach is yelling on the sideline, red in the face. Which coach from when you were a kid yelled exactly like that?
- A rookie checks in for his first minutes. What’s the first game you remember watching, and who was on the couch with you?
- The away fans start a chant. Which rival did you grow up hating, and is it still personal?
- The next episode starts in eight seconds. Which character in this show would you trust with your house keys?
- The season ends on a cliffhanger. What happens in the first five minutes of next season?
- The credits roll over the theme song. Which character’s job would you take tomorrow if it were up for grabs?
Sam: Anna used to ask “can we talk?” in the fourth quarter. Now she waits for a break and asks something about the game. Last Sunday it was which rival I grew up hating. We talked through all of halftime.
Side by side while he’s busy with his hands
He’s cooking, fixing the bike, building a shelf, two levels deep in a game. His hands are busy and his ears are free. Be the assistant, not the investigator: ask about the thing in his hands, and the talk will drift somewhere else on its own. If he answers in three words, hand him the screwdriver and wait.
- He’s tasting the sauce off a wooden spoon. What’s missing: salt, lemon, or more time?
- He’s chopping onions faster than you can. Where did you learn to cut like that: a job or a video?
- The recipe on his phone says “season to taste.” Do you follow recipes to the letter, or go off script by step two?
- He’s on his back under the sink with a wrench. What’s the first thing you ever fixed yourself?
- The bike is upside down on the floor with the chain off. What’s the longest ride you’ve done on it, and where did you end up?
- The flat-pack instructions are open to step 14 and there’s one screw left over. Go back, or call it a bonus screw?
- He’s lost to the same boss three times in a row. What does this guy do that keeps killing you?
- He’s building a base on a new map. If we lived in this game, where would our house go?
- He’s washing the car in the driveway. What car did you want at seventeen, and what did you actually drive?
- He’s painting a wall with the radio on. What’s the right playlist for a job like this?
On a call, when the line goes quiet
On the phone there’s no picture, just a voice. He might be driving, on the subway, or eating standing up. Swap “how was your day” for a small invitation to describe what’s around him. And a quiet line is not a failed call: two people can stay on while one of them makes tea.
- You hear a turn signal clicking. What’s out the windshield right now?
- There’s chewing on the line. What’s for dinner, and did you cook it or order it?
- The call keeps cutting out as the train hits a tunnel. What’s the next stop, and who’s sitting across from you?
- A TV is on somewhere behind him. What’s playing, and are you actually watching it?
- He says he’s standing at the window. Name three things across the street.
- He’s still at the gym, music thumping behind him. What song is playing in there right now?
- A dog barks somewhere close to him. Whose dog is that, and do you know its name?
- He’s walking home and you can hear his steps. Which shop on that block would you go into if it were still open?
- The line has been quiet for a minute. What’s the last thing you looked at before I called?
Anna: Our calls used to die right after “how was your day.” Now I ask what Sam can hear. Once it was a neighbor practicing the trumpet, and we stayed on for an hour guessing the song.
Waiting around: the line, the delay, the waiting room
You have time and nothing to fill it with. Don’t reach for “so, how’s work?”; look around. Lines and waiting rooms are full of things to name, and a small game for two beats scrolling side by side.
- The board flips your flight to “Delayed.” Pick a city on that board you’d switch to right now.
- The guy ahead of you at security unpacks a whole sandwich. What’s the strangest thing you’ve ever carried on a plane?
- You’re both at the gate with nothing to do. Pick one stranger here: where are they going, and what’s in the bag?
- The vending machine in the waiting room eats your quarter. What’s the worst coffee you’ve ever had because there was nothing else?
- The pharmacy line hasn’t moved in ten minutes. If you owned this place, what’s the first thing you’d change?
- The TV in the waiting room is stuck on a cooking show. With that basket of ingredients, what would you make?
- A suitcase rolls past covered in stickers. Which places would get a sticker on yours?
- The restaurant buzzer hasn’t gone off yet. What are you ordering first when it does?
- The line for the concert wraps around the block. Which song would ruin the night if they didn’t play it?
On the way home from someone else’s party
A friend’s wedding, a birthday, dinner at his parents’, a party at your friends’ place. The ride home is the best debrief of the week, as long as it’s about what you saw and not a review of the people. “So, what did you think of my friends?” is a test, not a conversation. If it turns serious on its own, there are deep questions to ask your boyfriend for that.
- You’re walking out of the wedding with your shoes in your hand. Which line from the toasts are you still thinking about?
- The DJ played the one song that put everyone on the floor. Which song gets you dancing, no matter where you are?
- His mom sent you both home with leftovers in foil. Which dish from tonight do you want the recipe for?
- His friend’s new apartment had a fish tank the size of a couch. What’s the one big thing you’d put in a living room if money didn’t matter?
- His friend’s brother told the canoe story again. Which story of yours gets told at every party, whether you like it or not?
- The kids at the party ran the whole evening. Which one of them was basically you at seven?
- The host’s playlist was stuck in 2009. What year would your party playlist be stuck in?
- The birthday cake had a sparkler instead of candles. What’s the best birthday you’ve had as a grown-up?
- You’re on the train home from his reunion. Who did you expect to see there and didn’t?
- You’re carrying the extra chairs back to the car. What part of tonight would you want to do at our place next month?
Sam: The ride home from my cousin’s wedding used to be silent. This time Anna asked which toast I’d steal. We argued about it for forty minutes and missed our exit.
The morning after a rough night
This one isn’t about last night. No replay of the argument, no “we need to talk about us.” The point is to get back to an ordinary day: coffee, breakfast, a plan for the afternoon, small things. Keep it short and easy. (If last night was more than rough and someone feels unsafe, that’s not a talking problem. Call 911 or the National Domestic Violence Hotline at 1-800-799-7233 (or text START to 88788). If anyone is thinking about self-harm, call or text 988. Outside the US, contact your local emergency services.)
- The coffee is dripping and nobody has said much yet. One cup today, or the whole pot?
- You’re both standing at the open fridge. Eggs, or the leftover pizza?
- It’s bright out and it’s Saturday. What’s one thing you want from today that takes under an hour?
- The toaster pops. If a diner delivered right now, what breakfast are you ordering?
- The plant on the windowsill looks as tired as you do. Water it, or give it a pep talk?
- The forecast says sun until three. Walk to the bakery, or stay in?
- The dishes are still in the sink. I wash, you dry, and you pick the music?
- The neighbor’s dog starts barking at the mail carrier. Same time every day: what do you think it’s yelling?
Anna: After our worst fight, I came into the kitchen with a speech ready. Sam asked if I wanted the last bagel. I said yes. The speech could wait, and by lunch it didn’t need saying.
Watching him do his thing
Pickup soccer in the park, the gym, the climbing wall, band practice, chess, fishing, helping a friend redo a bathroom. You’re not there to learn the rules; you’re there to see him enjoy something. Ask about the move you just saw, and about how it feels to do it.
- You’re on the bleachers at his rec-league game. Which play today do you hope I caught?
- He chalks up and stares at the wall for a full minute. Which hold on that route scares you?
- The drummer counts in at band practice. Which song in the set do you actually love playing?
- He’s leaning over a chessboard in the park. Which piece do you hate losing most?
- The fishing line has been in the lake for an hour and nothing. What does a good day out here look like, even with no fish?
- He’s sliding another plate onto the bar. What number are you chasing on this lift this year?
- He’s helping a friend tile a bathroom. Which part of this job do you secretly like best?
- It’s Sunday basketball with the same six guys. Who do you pick first, and who always ends up on your team?
- He’s trying the same skate trick for the tenth time. When it finally lands, what does that feel like?
None of these need to be good questions. They need to be about something real in front of you, asked once and then left alone. For a set made for the two of you, open the boyfriend deck, and for other evenings, browse all our articles. If you’re still at the start, get to know you questions are a better fit.