Questions to Ask on a First Date

The best questions to ask on a first date if you're tired of talking about jobs, weather, and where someone grew up. Designed to spark laughs, real stories, and the kind of connection that makes you forget you're on a first date.

First dates can be weird.

You're sitting across from someone you've chosen to spend a few hours with, trying to work out if there's chemistry, compatibility, or at the very least a decent story to tell afterwards. And yet somehow most first dates end up sounding like a job interview.

"What do you do?", "Where are you from?", "Got any holidays booked?"

Nobody's doing anything wrong. It's just that most people don't know how to get beyond the surface.

The best first dates aren't the ones where someone says all the right things. They're the ones where you both forget you're supposed to be impressing each other because you're too busy enjoying the conversation.

That's where great questions come in.

Not interrogation questions. Not "tell me your five-year plan" questions. Questions that create laughs, stories, honesty, and those moments where you suddenly realise you're talking to a real person instead of a dating profile.

Here are some of our favourite questions to ask on a first date from across the Loosen Up, Open Up, and Level Up decks.

Loosen Up

First date questions that make things fun

The goal here isn't to find your soulmate in seven minutes. It's to relax, laugh, and get comfortable enough to be yourselves.

1. What was your first impression of me?

Brave and surprisingly revealing.

Maybe they thought you were confident. Maybe they thought you looked intimidating. Maybe they thought you'd cancel ten minutes before the date.

Either way, you're getting honesty wrapped in humour.

Why it works: creates instant chemistry and usually leads to plenty of playful follow-up questions.

2. Your go-to karaoke song is...?

Forget music taste. This is about energy.

Are they choosing something iconic? Something chaotic? Something that guarantees they'll lose their voice before the chorus finishes?

The song tells you more than their Spotify Wrapped ever could.

Why it works: fun, low-pressure, and gives people permission to be a little ridiculous.

3. The most embarrassing thing you've done in public is...?

Everyone has one.

A wave that wasn't for them. Walking confidently into the wrong room. Calling a teacher "mum" and wishing for the ground to immediately swallow you up.

The best answers come with full storytelling mode activated.

Why it works: vulnerability disguised as comedy. A winning combination.

4. How would your best friend describe you in three words?

Most people know instantly.

The interesting bit comes afterwards.

Would they agree with those three words? Which one are they most proud of? Which one annoys them?

Suddenly you've learned more than you would've from twenty minutes of standard dating questions.

Why it works: reveals how someone sees themselves and how they think others see them.

5. As a child, you were obsessed with...?

Dinosaurs. Horses. Ancient Egypt. Magic tricks. Space. Random facts about sharks.

People light up when they talk about childhood passions. It's one of the quickest ways to see someone's genuine excitement.

And occasionally you'll discover they still own seventeen books on the subject.

Why it works: nostalgia makes people comfortable, and comfort creates better conversations.

Bonus Wildcard

Reader: Close your eyes. Then ask, ‘what colour are my eyes?’ 

Open Up

First date questions for real connection

This is where things get interesting. The kind of questions that take you a little deeper and help you understand who someone actually is.

1. What was the last thing that made you cry?

Could be laughter.

Could be a film.

Could be a conversation they weren't expecting to have.

The answer isn't really about tears. It's about what moves them.

Why it works: reveals emotional depth without feeling intrusive.

2. If money didn't exist, what would you be doing?

Strip away salaries, expectations, and practicality.

What's left?

The answer often points towards the things people genuinely care about, the passions they've put on hold, or the life they're quietly trying to build.

Why it works: gets to the heart of someone's motivations surprisingly quickly, and helps you better understand what lights them up. 

3. If you could relive one day, which would it be?

People rarely choose the obvious.

Sometimes it's a wedding.

Sometimes it's a random Tuesday with someone who's no longer around.

Sometimes it's a moment they didn't realise was special until years later.

Why it works: reveals what people treasure most. 

4. Which part of me do you wish to know better?

A surprisingly confident question. You're not asking whether someone likes you. You're asking what they're curious about.

Maybe it's your sense of humour. Maybe it's your ambition. Maybe it's the story behind something you've casually mentioned and moved on from.

The answer tells you what they're paying attention to, and what they find interesting about you.

Why it works: creates genuine curiosity in both directions and turns the spotlight back on the connection itself. It shows interest, confidence, and is guaranteed to spark a better conversation than "so, where do you see yourself in five years?"

05. What did you learn from your last relationship?

Not who was right. Not who was wrong. Just what they learned.

The answer often tells you more about emotional maturity than anything else you'll ask all evening.

Why it works: shows self-awareness without turning the date into relationship therapy.

Bonus Wildcard

Swap phones and write each other a message in the notes. Only read it once you’ve left. 

Level Up

First date questions that leave you thinking

You've laughed.

You've opened up.

Now let's talk about the questions that tend to stay with people after the date ends.

01. If tomorrow was your last day, you'd regret never...?

The answer arrives surprisingly fast.

Start the business.

Write the book.

Move abroad.

Tell someone how they feel.

Most people already know. And if they don’t they’ve probably never even thought about it, which makes this question really powerful in highlighting something they’re craving, but perhaps haven’t put words to. 

Why it works: takes you down the path of priorities, dreams, and paying attention to that one thing that’s really calling them.

2. What three things do you value most in life?

A lot of people might say ‘happiness’. Sure, it’s an easy answer.

The interesting bit is what comes after.

Freedom. Family. Curiosity. Adventure. Stability. Growth.

Whatever appears on that list tells you a lot about what’s truly important to them.

Why it works: gives you a glimpse of someone's internal compass, and the things that make them feel complete. 

3. What's something you've discovered about yourself in the past year?

People change constantly.

We just rarely stop to acknowledge it.

This question creates space for someone to recognise their own growth, and to feel gratitude for it.

Why it works: positive, reflective, and often unexpectedly meaningful.

4. What do you crave more of?

Not ‘what do you want?’

What do you crave?

Adventure?

Peace?

Connection?

Confidence?

The wording changes everything.

Why it works: gets past goals and into deeper desires.

5. What are you not saying yes to in your life, and what's stopping you?

Some people know the answer before you've even finished asking. Others have never even considered it. 

Either way, once they've said it out loud, it suddenly feels not just more real, but highlights how they can start saying ‘yes’ and what that ‘yes’ will give them. 

Why it works: helps people articulate the thing they've been avoiding, and through the conversation that follows, perhaps a way to change that ‘no’ into a ‘yes’. 

Bonus Wildcard

Both players: Create your own uplifting affirmation for the week. Repeat it when you wake up, before you sleep and throughout the day. 

Check in this time next week to see the effect it has had. 

Our #1 Tip for Having a Great First Date

The secret isn't finding the perfect question.

It's caring about the answer, and asking follow-up questions. 

Most people hear an answer and immediately start preparing their own.

The best conversations happen when you're genuinely curious enough to stay with what was just said.

Imagine someone tells you they'd spend their life travelling if money didn't exist.

Most people jump straight to their own answer.

The better move?

"Where would you go first?"

"What's stopping you now?"

"What do you think you'd find there?"

Three follow-ups later you're no longer having a first-date conversation.

You're having a real conversation.

That's the difference.

The goal isn't to impress someone.

It's to discover them.

And if you're both doing that at the same time, the date usually takes care of itself.

These questions work whether you're grabbing coffee, sharing drinks, walking through a park, or sitting across from someone wondering if there's a second date on the cards.

Because great first dates aren't built on perfect answers.

They're built on genuine curiosity.

Death of Small Talk was created to help people move beyond surface-level conversation and into the kind of moments that actually matter. One question can change the entire direction of a date. Sometimes even a relationship.

You just have to ask it.

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