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First date questions: easy, funny and fun ones to ask

The hardest part of a first date is the first ten minutes. After that, one good question usually carries the rest of the night. Here are easy, funny and fun ones to keep it flowing.

The best first date questions are easy to answer and hard to be boring with: a funny opener, a this-or-that, a story prompt, then one that earns a second date. Ask like you're curious, not interviewing, and share your own answer. Below are 36, sorted from easy to second-date-worthy.

capybara cards team · 2026-10-12 · 6 min read

Good first date questions do one job: they get the other person telling a story. Not reciting their CV, not listing their hobbies, but actually telling you something with a beginning, a middle and a "wait, really?"

That's why the best questions are small and specific. "What do you do for fun?" gets a shrug. "What did you almost order instead of that?" gets a laugh and a confession about their weakness for mozzarella sticks. Here's a list built that way, sorted by the stage of the night.

Easy first date openers

For the first ten minutes, while you're both still figuring out where to put your hands.

• What did you almost order instead of that?
• How did the rest of your day go before you got here?
• Which part of this neighbourhood do you know best?
• What did you have for breakfast, and was it a good choice?
• What's the smallest plan you have for this weekend that you're weirdly excited about?
• Are you a window seat or an aisle seat person on a bus?

More easy openers like these are in the Getting to Know deck in the app. 149 more cards are in the Getting to Know deck.

Funny first date questions

Laughing together is the fastest way past the nerves. These also make great fun date questions for couples who've been together for years.

• Has a seagull or pigeon ever stolen food straight out of your hand?
• Which haircut from your school photos should be legally destroyed?
• What's a food you pretend to like at family dinners?
• If your dog or cat could rate you as a roommate, how many stars?
• Which ringtone or alarm sound do you hate with your whole heart?
• Which snack have you eaten so much of that the shop staff know your face?

The app has a whole pile of silly ones for when you want to keep the laughs going.

This or that first date questions

Quick picks, no explaining needed. Then ask "why?" and watch a two word answer turn into a story.

• Pancakes or waffles at a diner at midnight?
• Bookshop wander or record shop wander?
• Cinema in the front row or the back row?
• Beach holiday with a paperback or city break with a step counter?
• Board games where you win or board games where you laugh?
• Sunrise hike or sunset rooftop?

There are more quick picks in the Would You Rather deck in the app. 171 more cards are in the Would You Rather deck.

Never run out of things to saycapybara cards has Getting to Know for new connections, Would You Rather for quick laughs and Hot Takes for a friendly debate. One phone, no setup, perfect for a second date game night.Get the app

• Getting to Know149 cards
• Would You Rather171 cards
• Hot Takes90 cards

Questions that pull out a story

Once you're both relaxed, go for questions that need more than one sentence.

• Which weird job did you do for one summer, and would you go back?
• What's a trip that went completely off the plan in a good way?
• What's the best thing you ever found on the street or in a charity shop?
• What's a time you laughed so hard you had to leave the room?
• Which teacher's catchphrase can you still do an impression of?

Story questions are all over the app, mixed in with the quick ones.

"Tell me about" prompts

Sometimes a prompt works better than a question. "Tell me about" sounds curious instead of quizzing, and people tend to answer it longer.

• Tell me about the last thing you got slightly obsessed with.
• Tell me about a place you go when you need to think.
• Tell me about your best friend in one sentence.
• Tell me about the most underrated snack in your cupboard.
• Tell me about a family recipe that nobody else can make right.
• Tell me about a hobby you quit but secretly miss.

The app has more prompts like these for when the conversation needs a nudge.

First date questions to ask him

A few that tend to get guys talking, mostly because they're about things he's quietly proud of.

• What's a dish you'd cook to impress someone, and has it worked?
• What's a sport you'd watch for hours, and which one sends you to sleep?
• What's your signature move at a barbecue?
• Which video game or film did you love so much you rewatched or replayed it?
• What did your friends say when you told them you were coming tonight?

More questions to ask him are waiting in the app. 149 more cards are in the Getting to Know deck.

First date questions to ask a girl

Looking for questions to ask her that aren't the usual "so what do you do"? These are light, specific and a little playful.

• What's a song you'd belt out in the shower, no shame?
• What's your perfect lazy Sunday plan from start to finish?
• Which friend would you send a photo of tonight's outfit to?
• What's your favourite little treat to buy yourself after a long week?
• What's a skill you picked up from your mum or grandma?

There are plenty more to ask her in the app, sorted by mood. 149 more cards are in the Getting to Know deck.

Second date worthy questions

These quietly plant the seed for next time. If the answer is good, you already have a plan.

• Which restaurant in town would you take me to so I see the real you?
• Is there a game you'd want to teach me sometime?
• What's a song you'd put on in the car if we drove somewhere?
• Which day trip within two hours would you pick for a lazy Sunday?
• Is there a market or festival coming up that you've been meaning to check out?
• Which dessert place would you drag a friend across town for?

If you get to a second date, a card game is a great low pressure plan. The app has 42 decks and over 7,800 questions on one phone.

First date dos and don'ts

A few rules that make every question above work better.

Do:

• Answer your own questions. Ask, listen, then share. A date is a swap, not a podcast interview.
• Follow up on the details. If they mention a dog, ask the dog's name. Specific follow ups show you're listening.
• Let silence happen. A two second pause is not a disaster. Take a sip and smile.
• Keep your phone face down. Nothing kills a story faster than a glance at a notification.

Don't:

• Don't fire off a list. Three questions in a row with no reaction feels like a form.
• Don't bring up exes. Even if it's going well. Especially if it's going well.
• Don't go heavy too soon. Money, kids, politics and family drama can wait for a later date.
• Don't fake answers. If you've never seen the show, say so. Honest beats impressive.

The real goal

The best first date questions aren't clever. They're curious. Pick two or three from this list, keep the rest in your back pocket, and let the conversation go wherever it wants. If you leave knowing one weird, specific thing about them that you didn't know before, the date did its job.