Questions to ask on a first date (and how to ask them)

This guide starts with how to ask, because that's what turns a list of questions into a conversation. Then come more than 40 first date questions, grouped by kind. You don't need to learn them: pick a handful you'd genuinely like answered, and let the rest come from what the other person says. Like everything on My Cupid Dates, the advice here is for adults 18 and over.

For the practical side (where to meet, how long to stay and how to say goodbye), see our first date tips, and read meeting safely before any first meeting.

How to ask questions without it feeling like an interview

A question only opens the door. The follow-up is where you get to know someone. Ask what they do to switch off and they might say "baking, mostly". "Nice. Any pets?" shuts the door again and leaves you hunting for the next question. "What did you make last?" keeps it open, and the second answer is usually the better one.

The rhythm goes like this:

1. Ask something open

   Questions starting with what, how or tell me about invite more than a yes or no. "Do you like cooking?" gets one word, while "What's the best thing you've ever cooked?" gets a story, possibly a disaster.

2. Listen for the bit they care about

   Notice the detail they add without being asked, or the moment they speed up. That's your next question.

3. Follow up once or twice

   "How did that happen?" and "What was that like?" work almost anywhere. Two follow-ups feel like interest; six feel like a cross-examination.

4. Share something of your own

   Offer an answer of about the same size, so nobody is left out on a limb. A small confession earns a small confession, not your life story.

5. Hand it over

   Leave a gap for them to ask you something. If the last three questions all came from you, stop asking and tell them something instead.

That last step is the easiest to forget. When one person asks everything and the other answers everything, it's an interview, however good the questions are.

Easy first date questions to get you talking

If you met on My Cupid Dates, reread their profile before you go. The interests they've listed and their short introduction are the best source of first questions there is, because they're about this person and nobody else. "Your profile says you've just taken up running. How's that going?" beats anything below.

Easy warm-ups for the first ten minutes

These are small on purpose. Nobody has to think hard, and every answer gives you something to follow.

• How's your week been? Anything good happen?
• Have you been here before?
• Are you a morning person or a night owl?
• What's the best thing you've eaten lately?
• What are you watching at the moment? Anything worth staying up for?
• Are you a planner, or more of a see-what-happens person?
• If you weren't here, what would you be doing right now?
• Tea or coffee, and how do you take it?

What they love doing, and what lights them up

People sound different talking about something they love, and how they answer these tells you as much as what they say.

• What do you love doing when nobody needs anything from you?
• What could you talk about for an hour without getting bored?
• What's something you've got into recently?
• What did you love doing when you were ten? Do you still do it?
• Is there something you're quietly good at that most people don't know about?
• What's the last thing you got properly excited about?
• What are you looking forward to at the moment?

Tell-me-about questions that bring out stories

Stories show you what someone values without you ever having to ask.

• Tell me about the best holiday you've ever had.
• How did you end up doing what you do now?
• Tell me about a time you said yes to something on a whim and were glad you did.
• Who's the funniest person in your family?
• What's the worst job you've ever had?
• Tell me about a small thing that made your day recently.
• What's the best advice anyone's ever given you?
• When did you last laugh so hard you couldn't stop?

First date questions to ask her or him

You might have searched for questions to ask a woman, or a man. None of these change with who you're dating, and that's deliberate: assuming she won't care about football or he won't care about baking is the quickest way to sound like you're reading from a list. Ask the person, not the category. If you only remember five questions, make it these:

• What's the best thing that's happened to you this year?
• What do you do to switch off?
• What's the last thing you learnt that surprised you?
• What's the story behind your profile photo?
• What's something you'd love to do but haven't done yet?

Questions that go a little deeper, or a little sillier

Once you've both settled in, you can go further either way. Ask the deeper ones lightly and leave room for a short answer.

Gentle questions about values and what they want from dating

Nobody wants "So, what are your values?" across a coffee table, so these get there sideways. If you met through daily match suggestions, the big things may already line up on paper: they take account of beliefs and values, lifestyle habits such as drinking and smoking, and the kind of relationship each of you wants. These questions show how someone actually lives those things.

• What do your friends come to you for?
• What does a good weekend look like for you?
• What's something you're working towards at the moment?
• What's something you've changed your mind about in the last few years?
• What would make someone a terrible flatmate?
• What are you proud of that doesn't come up much?
• Whose relationship do you quietly admire, and what makes it work?
• What made you decide to give online dating a go?
• What are you hoping to find on here, if you don't mind me asking?

Playful what-if questions for a laugh

There's no wrong answer to these, which is the point. They show off a sense of humour (yours too) and loosen things up if it's all got a bit polite.

• If you could be brilliant at one thing overnight, what would you pick?
• What's your most controversial food opinion?
• If you could live anywhere for a year, where would you go?
• Cosy night in or big night out? Be honest.
• Which three people, living or not, would you invite to dinner?
• What's a small thing you'll happily argue about all day?
• What's your karaoke song, or the one you'd sing if someone made you?
• What's something everyone else loves that you just don't get?

Questions to save for later, and a few to skip

Some questions aren't wrong, just early. Keep these for a second or third date, when there's more time and a bit of trust:

• Exes, in detail. A passing mention is fine. Why it ended, and whose fault it was, can wait.
• Money. Salaries, debts and what someone's flat cost can make a first date feel like a credit check.
• Health. Medical history, medication and mental health are for people to share when they choose.
• Family plans, pushed too early. Children and timelines matter, and they'll come up. Asked over the first coffee, "How many kids do you want?" can make someone feel measured for a vacancy. If it's a deal-breaker, say so in your profile introduction.

If you're already planning that next date, our second date ideas should help. A few questions are best skipped altogether:

• "Where do you see yourself in five years?" It belongs in a job interview, and nobody enjoys it there either.
• "Why are you still single?" It sounds like a compliment in your head and an accusation out loud.
• "How many other people are you talking to?" That's their business, and asking turns the date into a contest.
• Anything about their weight or body. A warm compliment is fine; an assessment isn't.
• Exactly where they live or work. It's too much, too soon.

It works both ways. If you'd rather not answer something, "I'll save that one for another time" is a complete reply, and if a question feels off, trust your instincts.

Conversation topics for when it goes quiet

Every conversation has lulls, and a pause feels far longer from the inside than it looks from across the table. If it stretches, try one of these.

Say something about where you are. An observation is easier to answer than a question, because nobody's under pressure to be interesting. "That cake is the size of a small car" gives them something to pick up or laugh at.

Go back to something they said earlier. It proves you were listening, which makes it your best move. "You said your sister talked you into a half marathon. Did you actually run it?"

Own it with an honest, light line. "I had a brilliant question lined up and it's completely gone" tends to get a laugh and takes the pressure off you both.

If you'd rather have a topic than a question, the easy ones are food, trips you've taken or want to take, whatever you're watching or reading, pets past and present, something you're learning, and the best and worst things about where you each grew up.

How to tell they're enjoying it

A few signs are fairly reliable:

• They ask you questions back, and follow up on your answers.
• Their answers get longer as you go, with detail you didn't ask for.
• They bring up something you said earlier.
• They laugh easily and lean in rather than back.
• Their phone stays put and they lose track of the time.
• They mention something you could do together, even as a joke.

Short answers, glances at the door and no questions coming back point the other way. Give it time, though: some people take twenty minutes to warm up, and a shy person can say little and still be glad to be there.

What to ask in messages, and what to save for the date

Messages before a first date are mostly for finding out if you'd like to meet, and light questions do that well: "Is that you halfway up a climbing wall in your second photo?" If you're stuck on how to start, our first message examples will help.

Save the tell-me-about questions for the date itself. Stories are better out loud, where you can see their face and follow up straight away, and if you swap everything in messages there's not much left for the coffee. Leave a thread hanging instead: "I want the full story of that camping trip when we meet." It hands you both an opener on the day.

Our guide on how long to message before meeting covers the timing. Until you meet, keep the conversation on My Cupid Dates. If someone pushes to move it to a messaging app straight away, there's no need to agree: the site shows a warning when someone tries, because it's a common scam tactic. Our safety page has more on meeting in person.

However friendly the chat, never send money or gift cards to someone you've met online, and use block and report if anyone asks.

Quick questions

How many questions should you ask on a first date?

There's no number to hit. Aim for a roughly even share of the talking, and before you change the subject, either follow up on their answer or offer a bit of your own.

Is it a good idea to bring a list of questions?

Read one beforehand by all means, then put it away. Checking your phone for the next question makes the date feel like a quiz, and three or four you remember are plenty.

What if they don't ask me anything back?

Tell them something about yourself and leave a pause, which gives them an easy way in. If they still show no curiosity after a while, that tells you something about how they'd be to spend time with.

Should I ask about things from their dating profile?

Yes, it shows you paid attention. Pick one or two things rather than quoting the whole profile back, which can feel a little like being studied.

Are good first date questions different for men and women?

No. Ask about the person in front of you, their interests and their stories, and leave assumptions about what men or women like at home.