First Dates questions

Questions that skip the small talk and help you actually get to know someone. Here's a preview of the deck, grouped by vibe — get the free app to unlock all 137.

First Dates — Deep questions

The big questions worth sitting with.

• What three hours of your life would you choose to relive?
• What's the first thing you'd look for in a box of everything you've ever lost?
• What one thing about your future would you lock in if you could guarantee it?
• What question would you ask at the pearly gates?
• What year of your life would you live in forever if you had to pick?
• What would your younger self be most surprised by about your life now?
• What chapter title would you give this period of your life?
• When's the last time you felt completely like yourself?
• What's something you're scared to want?
• Who shaped who you are more than they probably know?

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First Dates — Real questions

Honest and grounded — drop the act.

• What is a green flag you notice about people almost immediately?
• What's a small win you've had this week that made you feel great?
• What's something you're currently learning how to do?
• What is the most meaningful advice you've ever followed?
• What are you most looking forward to in the next month?
• What's a hidden gem you've discovered recently?
• What's a question you wish people would ask you more often?
• What's something you've changed your mind about in the last year?
• How would you describe your energy today in three words?
• What do you think is the most important quality for a person to have?

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First Dates — Funny questions

Light prompts to get a real laugh going.

• Which reality TV show would you win?
• What's the most unhinged purchase you've ever made?
• What skill would you download into your brain?
• What's your warning label?
• What's a hill you'll die on that absolutely doesn't matter?
• What food have you been pretending to like your whole life?
• What's the dumbest thing you've ever cried about?
• What would your autobiography be called?
• What's your Roman Empire — the thing you think about way too much?
• What conspiracy theory do you kind of believe?

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First Dates — Flirty questions

Playful questions when sparks are flying.

• What's your idea of a perfect night in with someone you like?
• What's something that someone can do that instantly makes you more attracted to them?
• What's the most romantic thing you've ever done — or had done for you?
• What's something about you that most people find surprising in a good way?
• When's the last time someone made you genuinely nervous?
• What's a song that puts you in a mood?
• How do you know when you're really into someone?
• What's the first thing you noticed about me?
• What kind of energy do you think I give off?
• What's something you've wanted to say to me but haven't?

+ 37 more. See all 47 flirty first dates questions →

First Dates — Daring questions

No safe answers — go there.

• What would you do right now if you knew it couldn't hurt you emotionally?
• What memory would you delete if you could?
• What's your biggest dealbreaker that most people wouldn't expect?
• What's a red flag you've ignored before?
• What's the most impulsive thing you've ever done for someone?
• What's something people assume about you that's completely wrong?
• What's the most honest reason your last relationship ended?
• What's something you want to ask me but think it's too soon?
• What's something that's scared you about dating recently?
• What's a question you'd want answered before getting serious with someone?

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