What to talk about on a first date (and what to skip)

What should you talk about on a first date?

Talk about what the other person enjoys and cares about, ask questions that invite a story, and share your own answers too. The goal isn’t to assess them; it’s to find out whether you enjoy talking to each other. The best first-date conversations are curious, light and a little bit real.

Questions that work

Easy openers

• What’s been the best part of your week?
• What are you looking forward to this month?
• What’s your perfect free Saturday in the city?
• Which neighborhood would you move to tomorrow?
• What’s something you’ve gotten into recently?

A little deeper

• What are you working toward right now?
• Who’s the person you call when something good happens?
• What’s a trip that changed how you see things?
• What did you love doing as a kid that you still love?
• What’s something people are surprised to learn about you?

Fun ones

• What’s your most controversial food opinion?
• What would you be famous for, if you had to be?
• What’s the best thing you’ve eaten in New York?

What to save for later

• Detailed stories about exes.
• Your full list of deal-breakers.
• Salary, debts and heavy family or health history.

Big topics like politics or faith aren’t off limits if they matter to you — just ask with curiosity, not as a test.

How to get past small talk

Follow up. If they mention a trip, ask what surprised them about it. If they mention work, ask what they’d do if money weren’t a factor. Then share something small but real in return. That back-and-forth is what turns small talk into a conversation.

Start the date already knowing what you share

Half of first-date nerves is not knowing whether you have anything in common. On Nonna Picks, a compatibility quiz shows you both which areas you share before you meet, so the conversation starts on solid ground. For where to go, see our first-date ideas in NYC.

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