Over Christmas, I went out with the lads for a few pints on our semi-annual pub night. I’ve known these lads – men, really, not lads – for over a decade. Our partners are friends with each other, and our kids are of a similar age. Suffice to say that we know each other very well.

Once the usual catch-up banter and good-natured ribbing subsided, emboldened by a few ales, and inspired by the awesome School of Life, with my friends’ quasi-permission, I steered the conversation to a deeper place. I asked: what was the last time you cried and why? I don’t recall asking any friend this question before.

I won’t divulge their answers – nor will I share mine – but what was of greatest interest to me was that after we had shared our vulnerability on the question of crying, the conversation flowed into places it hadn’t before. At the end of the night, I think that we all came away with much more understanding of one another.

That experience showed me that taking risks to connect on a deeper level offers immense rewards, even with those you think you know well already. So, I encourage others, especially men – who in my experience rarely dig deeper – to follow suit with friends. Dig deeper! Trade life’s truths.

But I don’t recommend deploying my question on crying, unless you are with your absolute besties. Instead, opt for some softer questions, such as these from the School of Life:

“What would you like to be forgiven for?”

“What are you embarrassed to admit?”

“In what ways have your parents influenced your choice of partner?”

“What was the best evening of your life?”

“What insecurity of yours holds you back the most”?