How can I handle this depressing situation?

You have to talk with yourself first. What would you rather do without, a life of sanity, contact with your daughter. If it were my situation, I would deal with it by telling her she was my daughter while I raised her. I gave her what she needed to face life as an adult. As an adult, she has become someone I do not care to know. I would then tell her she is not welcome to visit my home at any time, and make it clear I meant it.
Like I said, you first have to decide what you want for yourself. If she wrecks your happiness, that is not a do over; you have sacrificed the time you get for living your life to someone who does not care about whether you enjoy your life.

Tell her she is not welcome. If you don’t want to be that direct, tell her you won’t be home. If she shows up, don’t answer the door. If she tries to break in, call the police. This may sound harsh, but it sounds like she needs tough love and to not be enabled by any means.

Tell them both flat out that you will notify the police immediately on the hint of them being spotted in your neighborhood. Better yet, inform them that you’ve already notified the police. Embarrassing as it might be, advise your friends and neighbors to call the police at the sighting of them This is a hardball situation, and daughter or not, nothing good is going to happen to you from any involvement with either of them——and you know it already. It must be heart wrenching for you, but anything short of your visible open hostility is a waste of time. Any shred of sympathy or compassion will be rewarded with the further looting of your belongings. I’ve been in spots like yours and can testify from hard experience that if you’re considering anything short of hard cold rejection, you might just as well save time and pile your possessions on the front lawn replete with a “help yourself” sign.

You need a crash course in how to no longer be a co-dependent, how to stop enabling them.

It’s both your daughter AND the grandson. Both of them need to be responsible for their own lives.

If either shows up unannounced, do not let either of them in your house. Do not let either of them back in your lives unless clean and sober for at least six months.

And may I suggest you contact Al-Anon right now and ask for help in how to do this. They will help you.

If I was in your situation, I would encourage the healthy daughter to come visit whenever she is able to. At the same time the troubled daughter (and her son) would be cut off completely. It sounds harsh, but as @stanleybmanly has pointed out, expressions or displays of sympathy or compassion are lost on them.

In addition, I would check with local law enforcement, discuss her penchant for causing trouble, and ask them what avenues of recourse you have. Specifically, when they show up (as they will, sooner or later), could you file a file a criminal complaint against them for trespassing, disturbing the peace, or both. It sounds harsh, however, bringing them to the attention of law enforcement is exactly what both need.

All much appreciated but depressing great answers. She acts like she cannot understand why we don’t want them here. Just phone conversations are so manipulative it boggles my mind. They make me so unhappy because I and everyone else in our family feel it so strongly that he is going to end up in prison. All his friends are at least nineteen and some much, much older. They all steal from one another right in the neighborhood. Cops circle her “house” every single time she applies for food stamps here comes CPS , seeing if the toilet flushes, asking questions, etc and she loses it and resorts to dumpster diving. She sleeps in a 1970 Winnebago , the first model made and the copper wiring has been stripped out and stolen and it has mice and I’d really hate to see it. Most things I’ve given them are either stolen, burned by some accident or rated not what they wanted. Years of this. She has a card she can use for medical and dental for her son and not one single time has she ever taken him to the dentist. It’s free so what’s the problem? The bane of my existence. And why doesn’t she get a second job? “I have a low self esteem” is the excuse. The real answer is she’s lazy and they do drug testing.

Sometimes people are broken and we can’t fix them. As much as we want to, they are just messed up and no amount of work will make them right. Just don’t let them ruin your life. Cold but true.

Here is the unvarnished truth.

Until the underlying problem is dealt with nothing will improve for any significant amount of time in terms of her or your grandson. Why do I say that?

Because the real problem is that they’re both addicts and all the “drama” which you seem so puzzled about is just the usual chaos that accompanies a life of addiction.

You can question that or wonder about what can be done but it’s basically like putting bandaids on a gunshot wound. Until they both get their asses into an inpatient rehab facility (separately) followed by at least a year or more in a sober- living house so they can learn how to live without drug dependence, NOTHING will significantly change.

If this situation has persisted for years (presumably from when he was a child) then I can’t imagine that I’m the first person to be telling you this or advising you to REGULARLY attend Al-Anon meetings (these are for loved ones of alcoholics and addicts.)

As for what to say to her, this may sound harsh, but it’s what you should have told her a long long time ago. Until she has been through rehab and sober living, you will not continue to enable her addictive and chaotic lifestyle.

I know it’s difficult, but it really is as simple as that. Addicts are users. Period. And they will continue using others in order to maintain their addictions. Perhaps after enough people refuse to continue that cycle, they may reach bottom and seek help.

But until then, other than an organized intervention, the only thing you can do is work on yourself. That’s what Al Anon is for.

I’m also going to recommend a book which has been helpful to many dealing with exactly what you describe. I would suggest you start reading it immediately. It’s been around for awhile so is cheap and easy enough to get used on Amazon.

The title is: “Codependent No More” by Melody Beattie

I wish you the best.

@Aster There is a consistency to the answers of people in this thread providing you a solution to your problems, two of which are your daughter and your grandson. But you call them depressing great answers.

Our answer are given with the intent to make your life better by you addressing your codependence. None of your actions have made life better for daughter or grandson, you can only work on yourself, and if you stop enabling, there is a glimmer of hope that the addicts in your life might get clean, but only if you quit enabling.

What difference does it make how she lives? It only matters if you let her or the grandson take advantage of you, which seems to be something you allow.

Time to make both of them deal with the consequences of their lives.

I would tell her right off the bat, “I know you’re not planning to come here. Don’t come here. Don’t plan to come here.” That way, it’s clear and she knows ahead of time. That’s it – it’s your house and you don’t need that crazyness.

^^^^^ ..and she’d bring her dog and I sure don’t need that here either! What a nightmare with our two bichons growling and having a fit and her flea bitten dog digging holes. OMG
I have got to be an enabler because enablers don’t often know they’re enabling, right? And I don’t see how I’ve done that. I’m doing a rotten job of it since they have to scrounge for a warm place to sleep and a good dumpster full of fresh food. I’ve never bought them a car . I do admit to sending them used sleeping bags they said “smelled bad.” I just found out she has been driving with a suspended license.

@Aster Some good answers given here; I suppose they can’t help but be depressing since, as you acknowledge, the entire situation is depressing.

May I ask if you’ve made a decision about what to do next?

Enabler is too polite. Think chump, then act accordingly. An aggressively hard heart is your only remedy. I’m not saying that the 2 of them are incapable of change. I’m saying that any opportunity you take to “enable” them, postpones all hope of reform. Drop the hammer for the good of all concerned.