Hi, this sounds like a really difficult position to be in. I'm no expert, that's for sure, but that sounds like a lot of therapy. The poor guy what a terrible age to lose his mum and what devastating effects that would have, but I just can't help thinking that 27 years, every Monday is some therapy stint?!
I mean, is it possible that someone can get stuck in grief because that was the reason that they began therapy?
Obviously the only way to help him is to be supportive & maybe ask does he want to talk (though it sounds like you did that already?) and would it be possible to suggest that he try something other than therapy now? I am all for therapy, I advocate it, but part of it is knowing when to move on and live without therapy being a 'crutch' isn't it?
I don't think I'd suggest that he 'gave up' therapy because maybe that is not a good idea and if he did, he might blame you if he didn't cope so well, but if he did try something else then he may slowly move more toward that and away from therapy??
I don't know, maybe it's me, like I say I'm no expert and there could be a million reasons why he still goes, but it is a long time & therapy as effective as it can be, they say too much of anything isn't good?
Maybe if you found a book about therapy and how it can be addictive or difficult to move away from & said you thought he might find it interesting.
If he didn't have to go so deep into his feelings every monday of his life and did something for fun that could be what helps him. We all need to have free time doing something just for fun, could it be that that is what he's missing? Sounds like a week of work, the gym, therapy & a healthy diet could be a life that's a bit too serious.
Could you start having a pub quiz on a Monday night? Lol, why not? Or find something that you and a few others can only do on a Monday night, something fun.
I could be way off the mark here, just a thought, trying to help, hope it works out okay for you, he's a friend and you care but you can only take so much snapping back! Good luck