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 Questions
Warm Up
- What is the best thing that happened to you this week?
- What do your friends always come to you for?
- What is something you could talk about for an hour without getting bored?
- What is your idea of a perfect night in?
- What is a place you have been that changed you a little?
- What is the last thing you got really excited about?
- Are you a planner or a go-with-the-flow person?
- What is your go-to coffee shop order?
- What is a skill you are trying to learn right now?
- What is the best concert or show you have ever been to?
Get Real
- What is something people usually get wrong about you at first?
- What are you most excited about in your life right now?
- Who has had the biggest influence on who you are?
- What is something you are working on becoming?
- What made you say yes to tonight?
- What is something you are proud of that you rarely talk about?
- What does a good friend look like to you?
- What is a value you will not compromise on?
- How do you spend your time when nobody needs anything from you?
- What is a small thing that instantly makes your day better?
Go Deep
- What does a good relationship look like to you?
- What is something you have learned about yourself the hard way?
- What makes you feel at home with someone?
- What are you hoping to find right now?
- What is one thing you want someone to know about you early?
- What did the people who raised you teach you about love?
- What is something that is hard for you to let people see?
- What does trust look like to you early on?
- What does feeling understood look like for you?
- What do you want this next season of your life to feel like?