Questions for Couples

Easy questions to start with

Light questions for a car ride, a coffee, or the first few dates. They're quick to answer, and most of them come with a story attached.

1. 1What's the most you've ever spent on something you used once?
2. 2Which restaurant knew your order so well you didn't have to say it?
3. 3What's a phrase you picked up from a friend and now say all the time?
4. 4What's the longest you've waited in line for something, and was it worth it?
5. 5What's the best advice you've ever gotten from a stranger?
6. 6What's the strangest job you've ever had, even if it only lasted a day?
7. 7What's a hobby you've started at least three times?
8. 8Which group chat would you never leave, even though it's been on mute for months?
9. 9What's a store you can't walk past without going in?
10. 10What's the worst weather you've ever been caught out in, and where were you going?
11. 11What's a town you passed through once that you still think about?
12. 12Who would you trust to order for you at a restaurant without asking what you want?

Date night questions

For across a table, at the bar, or on the walk home. They're meant to be answered with a drink in hand and no rush to get anywhere.

1. 13What's the best night out you've ever had that cost almost nothing?
2. 14What's a restaurant you've walked past for years and never gone into?
3. 15If tonight were a movie, what genre would it be so far?
4. 16What's the worst date you've ever been on? Names optional.
5. 17What's something on this menu you'd never order, and what's the story behind that?
6. 18If you had $20 to plan my perfect date, what would we do?
7. 19What's the last thing you read, watched or heard that you can't stop thinking about?
8. 20Who's the most interesting person you've talked to this month?
9. 21What song gets you on a dance floor no matter how tired you are?
10. 22What's a question you wish people asked you more often?
11. 23If the people at the next table were guessing our story, what would they get wrong?
12. 24What's a place in this city you love that you think I haven't seen properly yet?

Fun and silly questions for couples

For when you want to laugh more than talk. You both answer, and you're allowed to argue about whose answer is better.

1. 25What's the most dramatic you've ever been about something tiny?
2. 26Which of your friends would be the first to go in a horror movie, and how?
3. 27What's a lie you told as a kid that got completely out of hand?
4. 28What's the most embarrassing thing you've said while trying to impress someone?
5. 29What's a food combination you love that most people find disgusting?
6. 30If you came with a warning label, what would it say?
7. 31Which kitchen appliance do you have a personal grudge against?
8. 32What's the longest you've ever committed to a bit?
9. 33What's the weirdest thing a stranger has ever said to you?
10. 34What would your autobiography be called, and what's on the cover?
11. 35What's the most chaotic thing you've seen happen at a family party?
12. 36If you got a tattoo on a dare tonight, what would it be and where would it go?

Deep questions for couples

Save these for a quiet night with time to spare. Offer your own answer first if your partner hesitates, and let them stop wherever they want.

1. 37What's a belief you grew up with that you've had to work to unlearn?
2. 38What's something you're still grieving, even a little?
3. 39What part of your life feels unfinished right now?
4. 40Who has been kind to you in a way you've never been able to repay?
5. 41What's the hardest thing you've ever had to say to someone's face?
6. 42When you picture yourself at 80, what do you hope you stopped worrying about?
7. 43Is there a version of your life you still think about, the one where you said yes to something you turned down?
8. 44Which friendship has changed you the most, and how?
9. 45What's something you need but find hard to ask for?
10. 46When you're anxious, what's the story you tell yourself?
11. 47What's a fear that has quietly made a lot of your decisions?
12. 48What's gotten easier for you with age, and what's gotten harder?

Questions about the two of you

Questions about your relationship itself. They bring back good memories, and every so often they surface something one of you has been meaning to say.

1. 49What's a story about us you've told other people more than once?
2. 50What's the first moment you felt you could fully relax around me?
3. 51What's something you were nervous to tell me early on?
4. 52What's something we do now that you never pictured doing with a partner?
5. 53What's a habit of mine you've picked up without meaning to?
6. 54What's a disagreement we had that you think we handled well?
7. 55If a friend asked what we're like as a couple, what would you say in one sentence?
8. 56What made more sense about me after you met my family?
9. 57What do you think we're better at than most couples we know?
10. 58What's a plan we made that never happened and you'd still like to do?
11. 59When did you last feel like we were completely on the same team?
12. 60What's something you think I underrate about myself?

Questions about the future

Plans, homes, and the life you picture together. Ask them out of curiosity. Nobody has to commit to an answer tonight.

1. 61What's a goal you've never said out loud because it sounds too big?
2. 62What's something you'd want us to save up for, even if it took years?
3. 63Which age are you most looking forward to, and why that one?
4. 64What's a city you could see us living in for one year, just to try it?
5. 65What do you want our home to feel like when friends walk in?
6. 66How do you want to spend your 50th birthday?
7. 67What's something you want to do for the people who raised you while you still can?
8. 68If we hosted a holiday at our place one day, who's at the table and what are we eating?
9. 69What's a habit you want us to build now that future us will be grateful for?
10. 70What do you want to keep exactly the same about our life right now?
11. 71What part of getting older together are you most looking forward to?
12. 72What's a risk you'd want me to talk you into, and one you'd want me to talk you out of?

Harder conversations: money, family and conflict

Not date night material, but these are the talks that save you from surprises later. Pick one, pick a calm evening, and don't try to settle everything at once.

1. 73What's the biggest money mistake you've made, and what did it teach you?
2. 74How do you feel about debt, and is there any we haven't talked about?
3. 75What's something you'd like to spend money on that you think I'd question?
4. 76How do you feel about lending money to friends or family?
5. 77What's one thing your family does that you'd like us to do differently?
6. 78If one of our parents needed to move in with us someday, how would you want to handle it?
7. 79What does your family worry about when it comes to us, if anything?
8. 80When we disagree, what do I do that makes it harder to sort out?
9. 81After an argument, what tells you we're really okay again?
10. 82Is there anything you've stopped telling me because of how I reacted the first time?
11. 83What's an expectation you had about relationships that turned out to be wrong?
12. 84Is there a topic you feel like we keep stepping around?

Questions for long distance and over text

Short enough to send between meetings and specific enough to get a real reply. Good for long distance, a work trip, or a slow afternoon apart.

1. 85What did you eat today that I'd judge you for?
2. 86What's something small you saw today that you wished I could see too?
3. 87What should we watch at the same time this week?
4. 88What can you hear right now, if you stop and listen?
5. 89What's a conversation you overheard today?
6. 90What's something you did today that would have made me laugh if I'd been there?
7. 91What's a place near you that you'd take me first, and what would we order?
8. 92If you could mail me one thing from where you are, what would it be?
9. 93What did you dream about last night, as much as you remember?
10. 94Rank your last three meals, worst to best.
11. 95What's one part of your daily routine I'd be surprised by if I watched a whole day?
12. 96What do you want to talk about properly on our next call?