Deep questions

What it's for

Some conversations stay on the surface not because there's nothing to say, but because neither person knows where to start. A question written by somebody else takes that awkwardness away: you didn't choose it, so you aren't running an interrogation, and whoever answers doesn't have to wonder why that one in particular. It works one to one, in a couple, between old friends, in a family, and it works alone too, as a prompt for a journal.

The three rules that make the difference

Ask permission. «Do you fancy a slightly more serious question?» changes everything: it offers the chance to say no, and whoever says yes has already decided to be in it.

Answer it yourself too. A deep question asked one way only is an imbalance: whoever answered feels exposed and the other doesn't. Answering first, or straight afterwards, brings the two people back to the same level.

Don't fix it. This is the commonest mistake and the hardest to avoid: faced with a difficult answer it feels natural to give advice, and nearly always that isn't what's wanted. The silence after an answer isn't a gap to fill, it's the part where thinking happens.

When it isn't the moment

Not in a big group, where nobody wants to be the first to open up in front of twelve people: there you want the light questions of Icebreaker questions. Not with someone you've just met. Not during an argument, because a deep question in the middle of a row sounds like a trap. And these questions are not therapy: if something that comes up is bigger than a conversation, the right thing is to say so and not pretend it can be held there.

Nearby tools

To break the ice in a new group there is Icebreaker questions, and for a lighter evening Truth or dare. If you want the questions as writing prompts, the word count of what you write is done by Word counter, and for a thought a day there is Motivational quotes.