"Behind every great man is an even greater woman".

It's no lie that dudes dump their shit on women more than they should.

This guy sounds like a drag.

Woof, that sounds like a lot. I'm glad you're still chatting to him and have nudged him towards an EAP, but do you think it would be beneficial to point out his constant negative viewpoint? It's nice that you want to possibly include him, but it sounds like it'd be fairly risky from a draining your energy view.

But haaaard agree that mates need to talk to mates. I noticed when boyo would catch up with his mates it's always incredibly superficial chatter, he's got no idea how his mates are doing in life. I asked about it and he said "that's just how they've always been. They'll talk if they want to." But will they?!

the observation about taking things literally really resonated with me

I have a strong tendency toward that, it's from too long in relationships where there was no joking or fun , also a lack of self trust in figuring things out

And I just this past week noticed Miss Seagoon is the same , I joked that the chairs and loos in NZ were all too low, and in a way laughing at myself for being a but unfit, and could barely get up. A half day long lecture on fitness and strength training for seniors ensued.

I just have to tell her not to be so serious and not take me so seriously. We do laugh a lot but not enough.

How did we get this way. More importantly, how to get past this. I think awareness is best. No need to pathologise everything, it's just a habit.

This does not sound like it will end well to be honest.