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First Date Questions — Free Dating Conversation Cards Online

Most first date questions are a job interview in disguise. These aren't. Start light, and if it's going well, the deeper levels are where you find out whether there's anything real here.

Play these 60 cards → 60 questions · 3 levels · free, no sign-up

Light · 20 first date questions

Easy openers. Safe for anyone.

Dating

What's been the highlight of your week?

Light · 01
Dating

Are you a planner or do you figure it out when you get there?

Light · 02
Dating

What's something you're into that most people find strange?

Light · 03
Dating

What did you do before this that you thought you'd do forever?

Light · 04
Dating

What's the best meal you've had in this city?

Light · 05
Dating

How do you actually spend a free Saturday?

Light · 06
Dating

What's a place you keep meaning to go back to?

Light · 07
Dating

What's the last thing you got genuinely obsessed with?

Light · 08
Dating

Are you close with your family, or is that a whole conversation?

Light · 09
Dating

What's something you're proud of that isn't on your CV?

Light · 10
Dating

What's your most-repeated album or artist?

Light · 11
Dating

What would you be doing right now if we hadn't met up?

Light · 12
Dating

What's a small thing that instantly improves your day?

Light · 13
Dating

Do you like where you live, or is it temporary?

Light · 14
Dating

What's a movie you'd rewatch tonight without complaining?

Light · 15
Dating

What did you believe as a teenager that you find funny now?

Light · 16
Dating

What's something you've learned recently?

Light · 17
Dating

City person, water person, or mountain person?

Light · 18
Dating

What's the best trip you've taken, and what made it good?

Light · 19
Dating

What are you looking forward to in the next few months?

Light · 20

Deeper · 20 first date questions

Personal, but not heavy.

Dating

What made you say yes to this?

Deeper · 01
Dating

What's something you're working on about yourself?

Deeper · 02
Dating

What kind of people do you end up closest to?

Deeper · 03
Dating

What's a decision that changed the direction of your life?

Deeper · 04
Dating

What do you want your life to look like in five years — honestly, not impressively?

Deeper · 05
Dating

What's something you used to want that you don't anymore?

Deeper · 06
Dating

How do you handle it when things go badly?

Deeper · 07
Dating

What's a friendship that shaped you?

Deeper · 08
Dating

What do you need from people to feel comfortable?

Deeper · 09
Dating

What's the last thing that made you rethink something?

Deeper · 10
Dating

What's a risk you're glad you took?

Deeper · 11
Dating

Where are you when you feel most like yourself?

Deeper · 12
Dating

What's something people assume about you that's wrong?

Deeper · 13
Dating

What did you learn about relationships from your parents?

Deeper · 14
Dating

What's a hard year you've had, and what got you through?

Deeper · 15
Dating

What are you not willing to compromise on?

Deeper · 16
Dating

What do you do when you like someone?

Deeper · 17
Dating

What's something you're still figuring out?

Deeper · 18
Dating

When did you last do something outside your comfort zone?

Deeper · 19
Dating

What's missing from your life at the moment?

Deeper · 20

Deepest · 20 first date questions

The ones that stay with you.

Dating

What are you actually looking for — and are you telling the truth?

Deepest · 01
Dating

What's the pattern you keep repeating in relationships?

Deepest · 02
Dating

What's something you'd want a partner to know early?

Deepest · 03
Dating

What's the loneliest period of your life been like?

Deepest · 04
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What do you think you're bad at in relationships?

Deepest · 05
Dating

What would someone who dated you say about you?

Deepest · 06
Dating

What's a fear you carry into every new thing?

Deepest · 07
Dating

What have you had to forgive yourself for?

Deepest · 08
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What do you want that you feel embarrassed to want?

Deepest · 09
Dating

What's the last time you were truly honest with someone about how you felt?

Deepest · 10
Dating

What kind of love did you grow up around?

Deepest · 11
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What would make you walk away from something good?

Deepest · 12
Dating

What are you healing from right now?

Deepest · 13
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What do you hope this turns into, if anything?

Deepest · 14
Dating

What's a version of yourself you left behind?

Deepest · 15
Dating

What do you struggle to say out loud?

Deepest · 16
Dating

When did you last feel completely understood?

Deepest · 17
Dating

What do you need more than you admit?

Deepest · 18
Dating

What would you want said about you at the end of it all?

Deepest · 19
Dating

What's the question you were hoping I wouldn't ask?

Deepest · 20

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