70 questions to ask on a first date, from the menu to goodbye

Before you order, while the menu is still open

The first five minutes are about tonight, not about your life story. Ask about the trip here, the day, the menu in your hands. (Meet somewhere busy, and remember that “I’d rather not say” is a full answer, both ways.)

• One of you is still unwinding a scarf. How did you get here tonight, and did the route go to plan?
• The menu is open and nobody has read a word yet. What were you doing an hour ago?
• There’s a drinks list full of names nobody can pronounce. Which one are you ordering for the name alone?
• The server rattles off the specials way too fast. Which one did you actually catch?
• You both stop on the same line of the menu. Which word in that description sold it?
• The menu has one safe dish and one you can’t picture. At a new place, which one do you usually end up ordering?
• You mention you almost walked past the door. What did you notice on this street on the way in?
• Your bag is still under the chair with the whole workday in it. What’s one thing from today you’re glad is over?
• The server asks if it’s your first time here. What’s the newest place you’ve tried this month?
• You’re both still deciding. Before you walked in, what did you think this place would look like inside?

While you wait for the food and the nerves settle

This is where people reach for the big questions. Don’t. Keep it small until the food arrives. Still picking a place? Here’s a deck of places for a first date.

• The menus are taken away. Which dish did you almost order instead?
• There’s a typo on the chalkboard by the bar. What’s the best autocorrect mistake you’ve ever sent?
• The bread basket shows up before anything else. Do you dive in right away or save room like a responsible adult?
• The playlist here seems stuck in one decade. Which decade’s music do you know every word to?
• The kitchen door swings open and you get a wave of garlic. What’s the dish you cook when you want to show off a little?
• The menu says everything is house-made. What do you make from scratch that most people just buy?
• The wait is getting long and someone’s stomach growls. Do you get hangry, and what’s your first warning sign?
• There’s a huge, strange painting above your table. What’s hanging on the walls at your place right now?
• One of you is folding the napkin into smaller and smaller squares. What do you fidget with when you’re nervous?
• A plate goes by to the next table and it looks amazing. What would you order here on a second visit, now that you’ve seen it?

Sam: I asked, “So, what are you looking for?” and the server arrived right on the word “for.” Anna ordered a lemonade and studied the ceiling. When he left I said, “Forget that. What did you almost order?” She laughed: “The lemonade was a panic choice.”

Over the food, when a follow-up comes easily

The whole trick is to trade: answer the question yourself, then ask, then follow up on what they just said. The last few below start with something they already told you.

• The food lands and the first bite is way too hot. Do you wait for it to cool down, or burn your mouth every single time?
• There’s a little bowl of sauce neither of you can name. What’s the sauce you’d put on almost anything?
• You offer them a bite from your plate. Are you a sharing-plates person, or does a fork on your side make you twitch?
• You notice one of you is eating around the best part. Do you save the best bite for last or start with it?
• The dish turns out spicier than the menu warned. How much heat can you actually handle?
• The portion is enormous. Do you take the rest home, and does it ever get eaten?
• Someone at another table sends a plate back. Have you ever done that, or do you eat it and say it was great?
• One of you is clearly a slow eater. Growing up, did you have to clean your plate, or could you leave what you didn’t like?
• They name what they do for work and move on fast. What part of it do you actually like talking about?
• They say they used to live somewhere else. What did you eat there that you can’t find here?
• They mention a hobby they picked up. How did you get into it, and how long until you were any good?
• They tell a story about a disaster in their kitchen. Once you’re done laughing: what’s the last thing you made that actually came out right?

Anna: The table had this green sauce, and Sam said it tasted like his aunt’s. I asked which aunt, and that was it: twenty minutes about a woman who brings a cooler of sauce to every wedding. I didn’t need another question all night.

When a pause lands and nobody wants to check a phone

A pause isn’t a failure. Two people who met an hour ago run out of words sometimes. Use what’s in the room, or say it out loud.

• It goes quiet and you both end up watching the bartender. What’s a job you’d want to try for just one week?
• The silence is long enough that you can hear the song playing. What would you put on right now to fix this quiet?
• Both phones are face down and staying that way. What’s the app you open when you have nothing to say?
• There’s a lull and your eyes land on the umbrellas by the door. Did you check the weather before you came out, or do you figure it out as you go?
• You catch the clock on the wall over their shoulder. On a normal weeknight, what time do you start winding down?
• Nobody’s said anything for a bit. Say it: “I just went completely blank.” What were you thinking about just now?
• The server walks by with a tray of coffee. Are you a coffee-after-dinner person, or will that keep you up until two?
• You admit the pause is just nerves. What helps you relax when you meet someone new?

Sam: I told Anna, “Sorry, my brain just left the building.” She said, “Mine too, it’s somewhere near the dessert menu.” The pause was over.

On the walk after, when there is no table between you

Outside, the table and the steady eye contact are gone. Talk sideways and ask about whatever you pass.

• You step outside and nobody has a plan yet. Do you know this part of town, and what’s around the corner?
• You pass a bar with a line out the door. Which place in this city is actually worth the line?
• The streetlights come on. What time of day are you at your sharpest?
• You notice one lit window high up in a building. Do you like living up high or close to the street?
• You walk past an empty shop with a “For Rent” sign. If that space were yours for a year, what would you open there?
• Someone is practicing scales on a piano behind an open window. Did you ever play something, and how far did you get?
• There’s a mural on the side of a building. If your block got a mural, what should be on it?
• You pass a gym window with rows of treadmills. How do you like to move during the week, if at all?
• You wait at a crosswalk for the light to change. How long have you lived here, and what still surprises you about this city?
• You pass a small park with a single bench. Is there a spot in this city that feels like yours?
• A bodega is still open, lights buzzing. What’s your late-night grab on the way home?
• The walk goes quiet in a good way. Do you go on walks to think, or only to get somewhere?

When it is going well and you want one level more

If the evening is easy, you can go one step deeper. Ask in a way that lets them choose how far: a short answer is fine, and so is a long one.

• They mention needing a quiet weekend soon. When you want a whole evening alone, what does it look like?
• They mention a class they just signed up for. What’s the last thing you learned to do, and who taught you?
• You pass a poster for something happening next month. What’s one thing you want to try in the next month?
• They mention their week was rough. What’s the small thing that gets you through a hard week?
• They say they’re bad at bragging. What are you proud of that would never fit on a résumé?
• The conversation turns to the people in their life. Who’s the friend you’ve known the longest, and how did you meet?
• They talk about a change they made this year. What small habit made your weeks better?
• They tell you about a moment they surprised themselves. When did you last do something you didn’t think you’d do?

Anna: I asked Sam what he does when he wants to be alone, expecting “video games.” He said he watches planes land from the airport deck. I liked that he told me something slightly strange.

At the goodbye, on the corner, at the stop, at the door

The goodbye isn’t the moment to grade the date or ask about the next one. Keep it small and end on something good.

• You’ve reached the corner where you’ll split up. What’s the part of tonight you’ll tell a friend about first?
• You’re waiting for the rideshare and it’s still four minutes away. What didn’t we get to tonight that you wanted to ask about?
• The app says the train is two stops out. What does tomorrow morning look like for you?
• Your car shows up on the map. Do you want a “home safe” text, or is that too much for a first date?
• The bus pulls up. What are you putting on in your headphones for the ride home?
• You’re standing at the turnstile and neither of you moves. When did you stop being nervous tonight?
• Coats are on and you’re outside the door. What surprised you about tonight?
• You’re both still talking about the food. Which dish tonight won, yours or mine?
• It starts to drizzle while you wait under the awning. How do you like to end a day like this: straight to bed or one episode first?
• You’re at your stop and the night is almost done. What’s the rest of your week holding?

At the goodbye, a question can also just be a sentence: “I had a really good time.” It’s enough. Exes, money, kids and politics can wait for later, once you know each other a little.

When the first date turns into a second and a third, the get to know you questions pick up where this list ends. For something sillier, try these fun questions for couples, and once you’re a couple, the 21 questions for couples. More lists live in our articles.