Deep questions to ask

Questions that go past small talk: what someone believes, fears, regrets and hopes for. Every set here is written to be asked of a real person, with a note on what each question tends to open up.

27 sets · 661 questions · each with a note on whyDeal me one at random

A few to start with

What is everyone at school talking about that adults have no idea about?
This casts them as the expert and you as the person who does not know, which reverses the usual footing. You will hear about apps, in jokes and incidents that no school newsletter will ever mention.
From: Deep Questions to Ask Teens
Is there anyone you have never forgiven?
Usually a sibling, an old friend, sometimes themselves. This is often the question that finally explains a family absence nobody in your generation was ever given a reason for.
From: Hard Questions to Ask Your Parents
What were you dealing with in your twenties that I missed?
There is normally a stretch where one sister was absorbed in her own life and simply was not looking. Naming the decade rather than the difficulty makes it easy for her to answer.
From: Deep Questions to Ask Your Sister
What does a good person do that a merely nice person does not?
Splits two words people use interchangeably. Most answers involve cost: the good person does the right thing when it is inconvenient or unwelcome.
From: Deep Questions to Ask
When was money tightest, and did we know?
The second half is the part that lands. Many mothers worked to make sure their children noticed nothing, and hearing what was happening behind an ordinary year reframes it entirely.
From: Deep Questions to Ask Your Mom
What do you wish you could say to our parents now?
Siblings are the only people who can hear this without it becoming a family incident. What they name is often something they have decided never to raise, and knowing it changes how you read family gatherings.
From: Deep Questions to Ask Siblings

Every set on this topic

All topics All Personal & Relational sets