Would you rather: date night edition
A would you rather date night works best as a set round: 20 dilemmas played in order, starting easy and getting warmer, with a follow-up after each one. The round below is built for that, and three shorter sets cover planning the date, the dinner table and the end of the night.
order for each other tonight
let the server choose for us
50 dilemmas, each with a follow-up · Updated November 12, 2026
Most date-night lists are a pile of questions you scroll through at the table. This page starts with a round: 20 dilemmas in order, from easy picks to the warm ones, sized for one dinner or one drink. After that come shorter sets for planning the date, for the table and for the walk home. Every dilemma has a follow-up.
- Play the 20-dilemma round in order. It's built to get warmer as the night goes on.
- One dilemma between each course or drink keeps it from feeling like homework.
- Each of you gets one pass during the round. Use it on anything you'd rather talk about at home.
50 dilemmas
A 20-dilemma round for tonight's date
Play these in order. The first five are easy, the middle gets personal, the last five are for when you're both relaxed.
Would you rather order for each other tonight
or let the server choose for us
Talk about itWhat would you order me?
What it revealsHow much each of you trusts the other's read of your taste.
Would you rather sit side by side at dinner
or sit across from each other
Talk about itWhat does each one feel like to you?
What it revealsWhether each of you feels closer touching or looking at each other.
Would you rather have a date with a twenty dollar budget
or have a date with no budget but only one hour
Talk about itWhat would we do with it?
What it revealsWhether each of you gets more creative with a limit on money or on time.
Would you rather go back to where we had our first date
or go somewhere neither of us has been
Talk about itWhat do you remember about that first one?
What it revealsWhether each of you leans toward nostalgia or toward something new.
Would you rather dance badly in public
or sing karaoke badly in public
Talk about itWhat song would you pick?
What it revealsWhich kind of public embarrassment each of you can handle better.
Would you rather have a picnic at midnight
or have breakfast at sunrise
Talk about itWhere would we set up?
What it revealsWhether each of you is more of a night owl or an early riser on a date.
Would you rather tell me about your worst date before me
or tell me about your best date before me
Talk about itWhat happened?
What it revealsHow each of you feels about talking about the past, and which stories you tell.
Would you rather rate our last date out of ten
or rate our first date out of ten
Talk about itWhat would bump it up a point?
What it revealsWhether each of you thinks your dates are getting better or the first one set the bar.
Would you rather swap roles for the night
or act like strangers meeting for the first time
Talk about itWhat would your character be like?
What it revealsHow much each of you enjoys playing a role and seeing the other in a new way.
Would you rather hear one thing I admire about you
or hear one thing I find attractive about you
Talk about itWhich one do you want first, and why?
What it revealsWhether each of you wants to be admired or desired more tonight.
Would you rather plan our next trip tonight
or plan our next year tonight
Talk about itWhere do we start?
What it revealsWhether each of you thinks in adventures or in the bigger picture.
Would you rather tell me a story you've never told me
or ask me anything and I have to answer
Talk about itWhat would you ask?
What it revealsWhether each of you would rather open up on your own terms or answer anything.
Would you rather kiss in the car before we go in
or kiss on the walk home
Talk about itWhich one feels more like us?
What it revealsWhether each of you likes affection before the night starts or after it ends.
Would you rather learn one new thing about me tonight
or remember one old thing you'd forgotten
Talk about itWhat do you think you don't know about me yet?
What it revealsWhether each of you is more interested in discovering new things or remembering old ones.
Would you rather end the night at a bar with a view
or end it on our couch with dessert
Talk about itWhat dessert?
What it revealsWhether each of you ends a good night going out more or settling in.
Would you rather hear something I've been nervous to say
or say something you've been nervous to say
Talk about itWhat makes things like that hard to say?
What it revealsWhether each of you finds it harder to hear something hard or to say it.
Would you rather stay up talking until 3am
or fall asleep early wrapped up together
Talk about itWhen was our best late night?
What it revealsWhether each of you feels closest through long talks or quiet closeness.
Would you rather have tonight be one we talk about for years
or have it be one of a hundred cozy nights like it
Talk about itWhat makes a night stick with you?
What it revealsWhether each of you values big memorable nights or lots of easy ones.
Would you rather end tonight with a plan for our next date
or end it with one thing we want more of
Talk about itWhat do you want more of?
What it revealsWhether each of you thinks about what's next or what you need more of.
Would you rather head home now
or stay out for one more round
Talk about itWhat would make you want to stay out longer?
What it revealsWhether each of you is ready to call it a night or wants the date to keep going.
Would you rather: planning the date
Use these before the date to decide what you're doing. Whatever you both pick, you go do.
Would you rather flip a coin at every turn of the date
or each plan half of it
Talk about itWhich half would you take?
What it revealsWhether each of you enjoys chaos on a date or a bit of control.
Would you rather take a cooking class
or take a pottery class
Talk about itWhat would we make?
What it revealsWhich kind of making things each of you would rather try.
Would you rather eat a fancy dinner in jeans
or eat fast food dressed up
Talk about itWhere would we go?
What it revealsWhether each of you cares more about the food or the feeling of dressing up.
Would you rather go to an arcade
or go bowling
Talk about itWho would win, and by how much?
What it revealsHow competitive each of you gets, and at what.
Would you rather go to a museum after dark
or go to a comedy club
Talk about itWhat would we talk about after?
What it revealsWhether each of you prefers a date that's quiet and curious or loud and funny.
Would you rather keep it within walking distance
or drive an hour somewhere new
Talk about itWhat's near us we haven't tried yet?
What it revealsWhether each of you values ease or novelty more when you go out.
Would you rather redo a date that went wrong
or repeat one that went perfectly
Talk about itWhat went wrong that first time?
What it revealsWhether each of you likes fixing what went wrong or repeating what went right.
Would you rather have a themed night at home
or have a mystery reservation out
Talk about itWhat would the theme be?
What it revealsWhether each of you enjoys creating the mood or being surprised by it.
Would you rather spend the whole date outdoors
or spend the whole date indoors
Talk about itWhat would we do?
What it revealsWhether each of you feels more at home outside or in.
Would you rather go out on a Monday
or stay in on a Saturday
Talk about itWhat makes that night feel special?
What it revealsWhether each of you finds a break in routine or rest more romantic.
Would you rather: at the table
For the wait between ordering and the food. Light, quick and good for people-watching.
Would you rather only order dishes you can't pronounce
or only order dishes you've had before
Talk about itWhat's the boldest thing you'd order?
What it revealsHow adventurous each of you is when it comes to food.
Would you rather get the chef's tasting menu
or get three appetizers and call it dinner
Talk about itWhich three?
What it revealsWhether each of you prefers a planned experience or grazing and sharing.
Would you rather sit at the bar
or sit at a quiet corner table
Talk about itWhere do we talk best?
What it revealsWhether each of you enjoys a lively room or a quiet one for talking.
Would you rather have a waiter who talks too much
or have one who forgets about us
Talk about itWhat's our worst restaurant story?
What it revealsWhich kind of bad service each of you would rather put up with.
Would you rather make a toast to us
or make a toast to the year ahead
Talk about itWhat would you say in it?
What it revealsWhether each of you prefers celebrating what you have or what's coming.
Would you rather be the couple laughing too loud
or be the couple whispering in the corner
Talk about itWhich one are we usually?
What it revealsWhether each of you is a little louder or a little more private as a couple in public.
Would you rather talk about anything but work tonight
or vent about work for ten minutes and then drop it
Talk about itWhat's on your mind from this week?
What it revealsWhether each of you needs to vent first or would rather leave work at the door.
Would you rather know what the couple next to us is arguing about
or know what they're celebrating
Talk about itWhat's your guess?
What it revealsWhether each of you is more curious about other people's drama or their good news.
Would you rather order a drink you've never tried
or order the same thing as me
Talk about itWhat would you try?
What it revealsWhether each of you likes to try new things or share the same thing.
Would you rather always pay the whole bill
or always split it exactly
Talk about itHow did we end up splitting things the way we do?
What it revealsHow each of you thinks about paying, and what fairness means to you.
Would you rather: the end of the night
For the walk home and after. These get a little flirty.
Would you rather walk home the long way
or get home as fast as we can
Talk about itWhat's waiting at home?
What it revealsWhether each of you wants the night to stretch out or move to the next part.
Would you rather have a nightcap and a long talk
or put on a movie we don't really watch
Talk about itWhat would be on in the background?
What it revealsWhether each of you ends a night better with talk or with background and closeness.
Would you rather get a back rub
or get a foot rub
Talk about itWho owes who one?
What it revealsWhich kind of touch each of you finds more relaxing at the end of a night.
Would you rather show me your best dance move
or teach me one I can't do
Talk about itWhat would you teach me?
What it revealsWhether each of you prefers to show off or to learn something new.
Would you rather make out in the car like teenagers
or make out on the couch like it's our first night
Talk about itWhich version of us comes out tonight?
What it revealsWhether each of you is in the mood for playful or for something slower.
Would you rather fall asleep tangled up
or fall asleep holding hands
Talk about itHow do we usually end up?
What it revealsHow each of you likes to fall asleep next to the other.
Would you rather end with breakfast plans
or end with no plans at all tomorrow
Talk about itWhat would tomorrow look like?
What it revealsWhether each of you likes the next day planned or totally open.
Would you rather write a two-line review of tonight
or pick one photo that sums it up
Talk about itWhat's the line or the photo?
What it revealsWhether each of you remembers a night in words or in pictures.
Would you rather say what you loved about tonight
or say what we should do next time
Talk about itWhat's yours?
What it revealsWhether each of you looks back on a good night or ahead to the next one.
Would you rather stay dressed up all night
or change into comfy clothes the second we're home
Talk about itWhat's your favorite thing I wear?
What it revealsWhether each of you feels more like yourselves dressed up or dressed down.
Questions people ask
How many would you rather questions should we play on a date night?
Twenty is a good number for one dinner or one drink: enough to get past small talk without taking over the night. The round at the top of this page is 20, ordered from easy to warm. If the conversation takes off on one of them, stop the round there. You can finish it on the walk home.
Is would you rather a good date night game?
It's one of the easiest, because it needs no cards, no board and no setup, and every pick comes with a reason you can ask about. It works at a restaurant table, in the car or on the couch. Couples who've been together a while often find it surfaces things they haven't talked about in years.
Can we play would you rather at a restaurant?
Yes. Keep the phone face up between you, read one dilemma, and both pick before you say why. Play one between each course so it doesn't take over the meal. The at-the-table set on this page is written for the wait between ordering and the food, and nothing in the main round is too private for a restaurant.