A few years ago, a really good friend of mine was going through a divorce.

I’d been friends with him for 20 plus years, but we rarely talked about intimate stuff like that. Our friendship was mostly about joking and carrying on.

For men especially, this is common. You will have the same friends you had in childhood, and yet you still don’t talk about how you feel or what you want out of life or just how tough it is sometimes.

And so it was really uncomfortable, but I asked him about it (after much “encouragement” from my wife). I asked him how he’s doing, and we talked for the first time about things like depression and relationships struggles, and it took our friendship to a new level.

And we’ve done that a number of times since. We’ve both become become fathers and that’s a whole barrel of shit to deal with. So we’ve opened up more and more.

This experience has broken a subconscious belief I had that a long-established friendship can’t change. It can’t get better. It can’t get deeper.

What I encourage you to do, if you’ve got long-standing friendships that are still somewhat superficial, is to go and ask an uncomfortable question that would make it more intimate, or share a struggle you’d usually hide, and just watch what happens.

Beware, however, that if your friendship is not truly healthy, you will get a bad reaction. This might be a necessary wake up call.

To take your connections to a deeper level, check out my Building Rapport course