Deep questions for family, partners and friends

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 a small lie you tell me to keep the peace?

Asked with a smile, it gets a real answer, most often "I'm fine" or "I don't mind." The small ones matter because they teach you both that smooth is worth more than accurate. Own up to one of yours.

From: Deep Questions to Ask Your Boyfriend

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

Which adult outside your family made the biggest difference to you growing up?

It might be a coach, a neighbor or a friend's mother, and it is someone they are seldom asked about and glad to describe. If nobody comes to mind, ask who they wish had been around.

From: Personal 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

Is failure really a good teacher, or do people only say so once they have recovered?

Workplaces like the slogan and seldom reward the failure. Look for a mistake that taught something no amount of advice could have, and what set it apart from the mistakes that taught nothing.

From: Thought Provoking Questions