One Question Deeper: First Dates & New Friends

You don't need more things to talk about. You need somewhere for the conversation to go.

280 questions and 560 follow-ups for getting past small talk. A first date, a new friend, a colleague you actually want to know.

Eight sections build in order: Easy Openers, What You Like, How You Spend Your Life, The Stories Behind You, How You See the World, People & Relationships, Who You're Becoming, and Should We Do This Again?

It starts where strangers can start. What food opinion could get you thrown out of a group chat? And it earns its way forward. What is the most fun you remember having as a kid? What is something you deeply appreciate about your family, and something that is complicated?

Depth markers keep you from going too far too fast, which is the usual way these evenings go wrong.

The final section is the one nobody else writes: how to close well, and how to say you would like to do it again. What is a moment tonight where you felt most like yourself?

Every question carries two follow-ups, because the second question is where people start to feel seen. Each also carries a cue for the listener: what to watch for while the other person answers.

Both people answer. Either may pass, with no reason needed. Delivered as EPUB. No DRM.