Alejandro Arce — home Thinking in Public
No. 47 · People

Questions for a date

Ten questions that skip the small talk. Start with: what is something you always wanted to do but never had the chance?

Line illustration: a small table for two with wine glasses and a large question mark floating between the chairs.

Small talk gets you nowhere. Weather, traffic, "so what do you do" — you can sit across from someone for an hour and learn nothing about who they are.

A good question does in two minutes what small talk can't do in an hour. It's just giving the other person a real door to walk through instead of a hallway.

Here are ten I actually use.

Ten to start with

01
What is something you always wanted to do but never had the chance?
02
What makes you feel truly alive?
03
What is one thing you wish more people understood about you?
04
If we could teleport anywhere right now, where would we go?
05
When was the last time someone truly made you feel seen?
06
What song feels like the soundtrack of your life?
07
What is something small that always makes you smile?
08
What's the most powerful compliment you have ever received?
09
What kind of moments do you wish could last forever?
10
What would you do right now if you had no fear?

Start here — any one of these beats "how was traffic"

Ask one, then actually wait for the answer. Don't queue up the next question while they're still talking. The good ones come from listening.

Going deeper

Use your judgement on these. They're for when the conversation is already flowing and there's real chemistry.

11
What's that secret side of you that most people miss but you secretly wish guys would see?
12
What makes you excited — like butterflies excited, or nervous?
13
What's a fantasy you would like to come to life but haven't yet?
14
If today were the last time we chatted, what would you share with me — an honest release?
15
What makes you feel super alive and a little exposed?
16
How do you recharge — alone, or with people?

I keep three of these lists: one for dates, one for meeting people, one for couples who've been together a while. Same idea each time — ask the real thing.

Ask the real thing.

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