The best fun questions to ask your partner are easy to answer and still tell you something new. Here are 100 original ones, sorted by mood, so you can pick five and start in under a minute: quick starters, silly what-ifs, questions about the two of you, favorites, date night ideas, would you rather, and a short optional set of flirty ones. About 40 are printed below, and the card deck at the top of the page deals from the full set. Take turns, skip anything you like, and stop while it's still fun.
I'm Oliver Drakeford, a licensed marriage and family therapist in West Hollywood. I use light questions like these to open every date night, because they make it easier to talk about more personal things later.
How do you use these questions?
- Pick five. Choose five questions that sound fun, or start with the first five in the next section. You can always ask more.
- Take turns, and both answer. Ask a question, then share your own answer instead of only listening to theirs. It turns a quiz into a conversation.
- Ask one follow-up. "What made that your favorite?" or "How did that happen?" often leads to the best story of the night.
- Skip anything you want. Either of you can pass on any question without explaining why.
- Stop while it's still fun. Five to ten questions is plenty for one sitting, and ending early makes it easier to do this again.
Quick fun questions to ask your partner (start here)
Mood: easy. Each one takes a few seconds to answer and works anywhere, from the dinner table to the car.
- What century would you live in if you could live in any time?
- What's the best meal you've eaten this year?
- If you could have any superpower for one day, what would you pick?
- What's your favorite childhood memory?
- What's the most useless talent you have?
- What's a family tradition that you love?
9 more quick questions are in the card deck at the top of the page.
Silly what-if questions to ask your partner
Mood: curious. These are for imagination and laughter, and there are no wrong answers.
- If animals could talk, which one would be the rudest?
- If we started a business together with zero experience, what would it be and who would be the boss?
- If you could swap lives with a fictional character for a week, who would it be?
- If you could only eat one meal for a month, which one would you choose?
- If you were famous for something ridiculous, what would it be?
- If you could add one new holiday to the calendar, what would we celebrate and how?
9 more silly what-if questions are in the card deck at the top of the page.
Fun questions to ask your partner about the two of you
Mood: remembering. These bring out shared stories and the inside jokes only the two of you know.
- What was your first impression of me, and how has it changed?
- What's an inside joke of ours that nobody else would understand?
- What's the funniest thing that has happened to us?
- What's a small thing I do that you'd miss if I stopped?
- When did you first realize we were really good together?
- What's something you've wanted to try together but haven't mentioned yet?
9 more questions about the two of you are in the card deck at the top of the page.
Food, music, and travel questions to ask your partner
Mood: easy. Favorites are quick to answer and often lead to a story.
- What's the vacation that you love the most?
- What's your ideal breakfast on a day with nowhere to be?
- What's the best concert, show, or live event you've ever been to?
- If you could eat at any restaurant in the world tonight, where would we go?
- What's the best snack combination you've ever invented?
- Which three songs would be on the soundtrack of your perfect Saturday?
9 more favorites questions are in the card deck at the top of the page.
Fun date night questions to ask your partner
Mood: curious. These ask for a story or a plan, and they work at the table or on the couch.
- If we had a free Saturday and no budget limit, how would you want us to spend it?
- How can we turn mundane tasks like running errands into enjoyable experiences together?
- What is something that you wish we could do more often together, realistic or not so realistic?
- What's a date we've never had that you'd like to try?
- If we had to plan a date with a ten-dollar budget, what would we do?
- What's a class or workshop we could take together just for laughs?
9 more date night questions are in the card deck at the top of the page.
Would you rather questions for couples
Mood: playful. Pick one, explain why, and then ask your partner.
- Would you rather have a personal chef or a personal driver?
- Would you rather live somewhere always warm or somewhere with four true seasons?
- Would you rather be able to pause time or rewind it by ten minutes?
- Would you rather give up coffee or give up dessert?
- Would you rather spend a month in a tiny cabin or a month on a boat?
- Would you rather always know what time it is or always know what the weather will be?
9 more would you rather questions are in the card deck at the top of the page.
Flirty questions to ask your partner (optional)
Mood: flirty, only if you both want to. These are written for adult couples who want a romantic tone, so skip this section if it isn't your style tonight.
- What's something I wear that you really like?
- When do you feel most attracted to me?
- What's a compliment you secretly love hearing?
- What's a small gesture that instantly makes you feel wanted?
6 more flirty questions are in the card deck at the top of the page.
How do you get more out of a fun question?
Follow the tangent. If the century question turns into a debate about whether you'd survive without coffee, let it.
Listen for the wish underneath. A wild answer often holds a simple want. "I'd live in Paris in the 1920s" might mean "I'd love to dress up and go out with you more."
Keep it light on purpose. If a fun question touches something tender, you can stay there or come back to it another night.
Why start date night with fun questions?
Fun questions warm up the room. Nobody wants to be handed a heavy question the moment they sit down.
They also keep curiosity alive. Couples who've been together a long time often feel they know every answer already. A playful question shows that isn't true. In one of my videos I put it this way: "All of that time spent together over the course of years gets traded in for familiarity, and familiarity kind of kills curiosity."
What if a fun question leads somewhere deeper?
A fun question can lead somewhere more personal, because a memory or a wish often has a feeling attached. In another video I said: "What really shifts a relationship into closeness and connection is sharing feelings, not just thoughts."
If a light question opens a deeper moment, follow it if you both want to, and let the evening end there. If you want to go further another night, the date night questions for married couples page has questions sorted from gentle to challenging, and either of you can pass on any of them.
FAQ
What makes a question fun rather than awkward?
A fun question has no wrong answer, it's about imagination, memories, or preferences, and either person can skip it. Awkward questions usually feel like a test.
Are fun questions useful, or just a game?
Both. They help you learn about each other in a low-pressure way, and they make deeper questions easier later.
How many questions should we ask in one sitting?
Five to ten is plenty. Stopping while you're both still enjoying it makes it more likely you'll do it again.
Can we use these on a first date?
Most of them, yes. The quick starters, silly what-ifs, favorites, and would you rather sections work for people who are still getting to know each other. The sections about the two of you and the flirty questions are written for couples who already have some history together.
Are these questions okay for any kind of couple?
Yes. The questions say "partner" and don't assume that you're married, engaged, or any particular gender. If a question doesn't fit your situation, skip it or change a word.
How often should we ask questions like this?
Once a week is a good rhythm. The Thursday email gives you a new set each week.
Ten new questions every Thursday
Closer with every question.
Deepening Date Night is a free weekly email. Each Thursday morning (about 9am ET), ten questions arrive, ready for the weekend: five for you to ask and five ask-back questions for your partner, each set going from gentle to challenging. Get the Thursday email.