Most first-date conversations are trivia rounds.

Where are you from? What do you do? Do you have siblings? Have you been here before? These questions are fine. They're also completely forgettable, and they tell you almost nothing about whether there's actually something here.

A good first-date question is specific enough to have a real answer and open enough to go somewhere unexpected. It's a question you haven't answered a hundred times before — which means you have to actually think, and so do they.

Here are questions that work.

Questions that reveal how someone thinks

1. What do you believe now that you didn't a year ago?
2. What's something you used to think was important that you no longer care about?
3. What's a question you're sitting with right now — something you don't have an answer to yet?
4. What's something you've changed your mind about recently?
5. What's something most people get wrong about the thing you do?
6. What's an idea you've been thinking about a lot lately?
7. What did you think adulthood was going to feel like — and how close was that?
8. What's something you believe that's hard to defend in polite company?

Questions that reveal what someone values

1. What's something you do every day that you'd protect against a busy week?
2. What does a good day look like for you?
3. What would you spend more time on if time wasn't a constraint?
4. What's something you can't imagine giving up?
5. What's a place that means something to you?
6. What's something you learned from the last thing that didn't work out?
7. What's something you're proud of that most people don't know about?
8. What did you want to be when you were a kid — and what happened?

Questions that are a little more honest

1. What are you nervous about in the next year?
2. What's something you're still figuring out about yourself?
3. What's a thing you're not good at that you wish you were?
4. What's the nicest thing anyone has done for you recently?
5. Who taught you the most about the kind of person you want to be?
6. What's something you know how to do that would surprise me?
7. What do you do when you're having a genuinely bad day?
8. What's something you've been putting off that you should probably just do?

A note on first-date questions

The goal isn't depth for its own sake. It's to find out if this person is interesting when they're being honest. Some people are. Some people aren't. A question like "what do you believe now that you didn't a year ago" finds that out faster than thirty minutes of résumé comparison.

You don't need to ask all of these. Pick one. If it leads somewhere, follow it. That's the whole method.

More in the app

GoDeeper has a First Dates deck with questions like these — calibrated for the early moments of something, when you're still finding out if there's actually something here.

Download GoDeeper for iPhone →

Related

• Values-aligned questions for dates 3–5 →
• GoDeeper for dating →