This is a first world problem so I feel bad even asking about it. DH and I are comfortably off. My brother, who lives in another country, isn’t. He is self-employed and his business hasn’t been doing well, even before Covid. He is a recovering alcoholic who let things slide. His wife, who kept their finances under control, finally washed her hands of him ten years ago and I can’t say I blame her. He has been with his new partner since his post-divorce rehab and she has helped him two or three times to get back on the wagon, the last time with an ultimatum. As far as I know he’s been TT for a good couple of years.
Nevertheless, his business isn’t making ends meet. Or something. It involves him making big cash layouts which he can’t always recover from his clients – the weather gets in the way, or the client goes back to England. (I don’t understand why he doesn’t get payment on account, but that’s beside the point.)
So every six months or so he asks us for a big bailout. These are always couched as loans but of course there is never anything formal (that would be unthinkable) and since his divorce we have never received a penny back, nor do we expect to.
It’s coming to a lot of money over the years. I honestly don’t know what would become of him if we didn’t help. His partner works hard, but in a low wage job. But I’m starting to feel resentful. Perhaps it’s my problem rather than his? I feel as if I’m going without things I’d like (a new car, for example) to help him out, though the things I’m going without aren’t things I actually need.
No other members of the family are aware of this. I don’t know if even his partner knows about it. DH is an absolute hero. If he resents it at all, he doesn’t show it. He just shrugs and says we do what we can, and we’d do it for any other member of the family too. And have.
But I feel my brother is taking the piss. He’s always resented the different life I’ve had ever since I did well at school, and this feels like his revenge. DH has suggested asking him man to man what steps he’s taking to put his business on a more practical footing, but that might appear overly aggressive. (DB is thin-skinned.) It’s not as if we can’t afford the subs, which look as if they will have to continue forever.
We are enabling him. I am reluctant to challenge him for risk of pushing him over the edge.
What would you do?
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Always bailing out DB – WWYD?
WagnersFourthSymphony · 18/08/2020 22:00
Parents long dead. He was the golden boy.
He is trained for this work. Too old for anything else. One of his sons helps him in the business - mercifully only on a sub-contracting basis. I suspect the current subs are to pay for the sub-contracts but it's only a hunch. His other son is in a different trade and doing well. Probably not well enough to sub his dad, though.
Yes, we have an adult son, earning a reasonable wage. He is OK - but would probably be shocked to learn of these subsidies. But generous, like his father.
I have a sister who isn't well off but frugal. She knows she can always turn to us for support but never has, probably never will. In our wills we will even it out between the siblings (and the amount will shock her dreadfully and piss off DB if he's expecting more) but that will be all rather late in the day. 
Is DB used to no consequences in life? Hmm, good question. He always feels hard done by. That it's all right for some. I've never really thought of it this way (always feeling the guilty undeserving one) but perhaps he's a bit inclined to tantrums and it's always felt like a bit of a success to keep him calm and even, and people around him happy rather than anxious. It's always been my problem, my fault. He's younger than me - there is a whole history there of how I was a selfish and neglectful older sister.
Perching We have subbed other relatives when they have needed it because we can. Especially in a low-taxed economy like ours it feels like a duty of those who are better off to look after those family members who aren't.
If we stopped paying him he might never speak to us again. Perhaps that wouldn't be a great loss in some ways - we have little in common - but I would need a long time to get my head round that. In my family, family is everything because that is all we have.
It's interesting seeing how I'm using family dynamics as an excuse. 
I wasn't really conscious of it till now.
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I feel you've adopted some sort of Lady Bountiful role with your brother that has almost a co-dependent element about it.
Just because you can afford to do something doesn't make it a good investment and I don't mean that in a financial sense but both in an emotional context and in regard to helping your brother in the long term.
Good call. No, there was never any question of it being any kind of investment or commercial loan - always just helping out a relative in temporary need. And yes, he does see me as a kind of Lady Bountiful - and resents me for it, as well he might. I don't like it either. But while you've got a LB around, you might as well make the best of it, eh?
But what else are families for? DH and I are from very different backgrounds but we both see it as a responsibility. Eg, he has offered to help his nephew banjaxed by Covid (nephew says they can cope OK for now, thank you but will bear in mind - all very grown up and straight forward). I'd be more than happy to help DN if needed.
But DB - I'm getting a bit fed up and feeling we're being taken for granted. Maybe we should just make a standing order and have done with it. Then he would accuse me of trying to humiliate him.
As for DS - no, he won't miss out. He will be generously provided for. As I said, we are comfortably off.
And no, I don't even see it as an investment in goodwill or family harmony, more as an obligation. And one I'd not mind being shot of. Not a family-minded person after all, really.
It's going to be a really difficult conversation with DB. DH has offered to do it and would do it brilliantly and tactfully but I'm not sure I have the courage to endure it even second hand.
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