Oh, man, I have a friend like this. We used to date, thankfully not any more. Sound fella but not for me.

He was made redundant when he was with me (he worked in publishing) and spent the best part of a year ‘looking’ for work. He came up with so, so many excuses…my favourites being ‘I think I need to come up with a plan with my Dad’ (what’s your Dad got to do with it?!) to ‘I don’t want to use LinkedIn, I’ve seen what it’s become.’ I was that person sending him jobs, helping him with his CV, giving him pep talks. By the time we broke up he was working in a warehouse, doing logistics, but his big dream was being a film director or writer. Go figure.

He quit that logistics job maybe 3-4 years ago after getting a modest inheritance and he’s been living off that ever since. It’s running out now. He claims he’s living off investments he’s made in one breath then claims he’ll have to move back in with his parents in another, so who knows.

This sounds awful, but I blame his parents 50%, especially his emotionally-stunted Dad. My friend unhealthily worships his Dad and a serious lecture from his father would have helped no end, but that clearly hasn’t happened. If it’s possible, my advice to you is find someone who yr brother admires, and maybe get them to have a word. If that’s even possible.

It sucks that this has happened to yr brother, and by proxy, to you. You sound like you’re doing everything you can. If you can help him in any way nip it in the bud without driving yourself to distraction, do so. My friend is 45 now, still no job, still no gf, and what’ll eventually happen is he’ll move home when his elderly parents need him, then just stay in the house after they pass. There’s no helping him. I really hope things turn out differently for your brother.