Have you ever had to let go of a friendship? How did you go about it?

I believe ditching him is the kindest thing you can do for him.
So he can find himself and pick himself up and not get enabled over and over into his self sabotaging cycles.
It sounds harsh I know but it's the truth.

No, it isn't cruel. Reasons aside, you are being used. "..for me to do the work for him.." tells me all I need to know, to know it is time for you to move on.

In a sense, continuing to help him is enabling him and dragging you down. He needs to sort himself out.

That wouldn't be cruel. He would have to face the truth about himself. That might lead him to seeking help.

You have come such a long way ...you don't need anyone weighing you back down...do what is best for you ...you don't need leeches ...he sounds like another drain 😕

I see it like a pre-cancerous growth or cist that has to be removed so you can maintain a healthy body. You have to cut him out or it will ruin the place where you have gotten yourself to.

I had a service buddy that was discharged under mental health issues, and he went the exact same route your friend has went. Lost his home, wife, custody rights to his children, and began to live in a rundown RV. The RV quit working and he did not have the money to fix or repair it himself and he could not move it off of the parking lot he parked on. After several days the police were called by the business owner, and he got into a fight with the police; got arrested and his RV impounded. Once sentenced in jail he went into a mental hospital, and once released he began to drift around smoking pot that led to crack cocaine. I had a few phone conversations with him and thought I should take him into my home to help him out. His older brother a veteran like us warned me not too because he was threatening to kill everyone, so I did not extend the invite into my home. A few months later when the elderly man that did take him in went to work my friend hung himself in the apartment of the elderly man.

It is a terrible rabbit hole to watch a friend sink into, but you have to protect you and your son sweetheart.

be safe, i see some red flags, with him being vindictive. i've cut ties many times for similar things, or sometimes just an instinctual bad feeling around them without knowing exactly why. usually i just told them straightforwardly that it's best to part ways. i learned it's better not to give a big explanation that makes it all about analyzing them, because they will only remember the negative after you leave and won't be able to let go. i just keep it short and sweet and make it about me and let them know i am no longer invested in the friendship, period. good luck!!! you are a beautiful person and you deserve people on your level.

Yes, I have. The friendship I had with this person was one I had never experienced. We were close and spent time together when we had the chance. But we made a fatal mistake. We decided to take it to the next level and start dating which eventually caused the relationship to fail, and our friendship to sour.

This shows that just because a guy and girl are good friends doesn't mean they are fit to be in a relationship. I learned that the hard way.

It can be such a bad feeling being around someone like that.

Sounds like he's got something stuck in his emotional craw.

I know it would feel cruel to ditch him, as you say, but under the circumstances, it would seem more cruel to yourself and your son, to not.

I am also dealing with a messy friend like that. He creates conflicts every now and than. Than call me to step in. He has caused me huge financial damages too. I am doing him a last favor this time and cutting him off from my life. I have told him in his face too

You don’t owe your friends endless compassion. Friendship is fragile and most friendships are transient things in life. Let him go and move on with your life. He will too.

He’s not even being your friend anymore, he is just trying to use you and take advantage of you. And you don’t have to tolerate that.

Sounds awful
If you're not coming away from being with someone lifted or at least nuetral they've got to go

That said I'm hopeless

I've been there and didn't sugar coat. I told them the truth and said only u can help u

And left
Never saw or heard from them again