What is the one question you always ask on a first date?
I have been on a fair few first dates this year, and I have noticed the ones that went somewhere all had a moment where the conversation stopped being small talk. For me that moment usually arrives when I ask: "What does a really good weekend look like for you?"
It sounds light, but the answer tells you almost everything — how someone rests, whether they need people around them, how much of their life is already full. I have learned more from that one question than from an hour of talking about jobs.
The best first dates are not interviews. They are two people finding out whether their ordinary days would fit together.
So I am curious what works for everyone else here. What is the question that reliably moves a first date past the surface for you? And has anyone got one that backfired badly?
- Bonus points if it works over coffee as well as over dinner.
- Extra bonus if it works on a video call first date.
