Relationship How Do I Know If It's A Valid Boundary To Set?

[Friday]

After posting I realized this is crazy. Of course this isn't a valid or reasonable boundary. I can't tell him or anyone how to live their life. I have to either give him the money or not. And it must be freely given with no strings.

I didn't post originally to your Q because... Yeah. This. ^^^^ The moment I give someone money, it's theirs, to do with as they wish. ((I also don't loan money. If someone wants to pay me back? Sweet! But the moment it leaves my hands, it's theirs, as far as my head goes. I'm not willing to lose a friendship over cash. And I have, before. So if I can't stand to lose it, I don't loan it -or in my case give it. ))

HOWEVER...

That doesn't mean I also don't give people my 2 cents ;)

I THINK that might be where you're conflating issues? There are some things going on in your friends life that you want to weigh in on, while at the same time don't feel comfortable loaning cash because of those issues (totally fair) // if those issues were addressed you wouldn't hesitate to loan the cash... So the struggle is that even if he hadn't asked for money.... You'd be wanting to have this convo with him? But the ask for money makes them inescapably entwined?

Maybe that's a way to go about it, however? Regardless of how he stabilizes his life, you'd want to see some stability before loaning him the capital for business = a totally fair boundary to draw IMO.

 

[feetfirst]

So the struggle is that even if he hadn't asked for money.... You'd be wanting to have this convo with him? But the ask for money makes them inescapably entwined?

@Friday Thank you so much for your two cents; it's easily worth a dollar :P It helps to hear and be reminded of what may be going on in his head. I know asking me for financial help triggers him and makes him feel very fragile, but helping him get on benefits may possibly be worse since he/we'd have to go into depth on the forms.

You hit the nail on the head by suggesting the two issues are getting conflated. I was very slowly trying to talk with him about getting physically stabilized before the money discussion came back up. He's in a dire place, and it isn't a reflection of his moral character. He does the best he can. He wants me to be proud of him and not see him as always in a bind and needing to be saved. Knowing how beneficial stable housing and disability would be for him (and eliminate the feeling of always needing to be saved), it's just so painful for me to watch him flounder and to feel like I'm enabling it to continue if I give him more money that will only postpone really addressing the issue. I hope he won't have as stringent an objection as yours when I bring up disability.

 

[EveHarrington]

FYI disability isn't easy to get. It's not a quick fix. He will likely need something to support him until he is approved.