First Date Questions
For getting past the resume and into the real person, without scaring anyone off. Curious, warm, a little playful.
Here’s how I use these: let someone pick the question they want to answer, and don’t rush to fill the silence after. The lists go from light to deep on purpose, so you can stop wherever the comfort runs out. The real magic isn’t the question — it’s getting curious about the answer.
The List
- What’s something that’s been making you happy lately?
- Are you more of a homebody or always out chasing plans?
- What’s a small thing that instantly makes you trust someone?
- What were you like as a kid?
- What’s something you’re genuinely excited about in your life right now?
- What’s a hobby or interest you could talk about for hours?
- What does a perfect, low-pressure day look like to you?
- What’s the most spontaneous thing you’ve ever done?
- What kind of people do you feel most yourself around?
- What’s something you’re working on becoming better at?
- What’s a value that matters more to you than people realize?
- What made you want to come out tonight?
- What’s a deal-breaker you’ve learned about yourself?
- What does feeling connected to someone look like for you?
- What’s something you’re proud of that you don’t usually lead with?