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I think boundaries are a very interesting topic but they should be a reflection of what we are prepared to put up with or tolerate. Whatever they are, they must be lines that other people can’t cross – for any reason.
They are not necessarily always to do with ultimatums but similarly they cannot be stretched or bent.
They do not always have to be major, in fact some small ones which are easy to put in place can have a very big impact.
Like you, I had lots of supportive conversations, frequently to no avail. The times when I was allowed in usually followed a large episode of gambling (similar to your last one) and I would think, this is it, maybe this time etc etc only to find history repeated itself time and time again. I eventually realised that the response I would get just depended on where he was in his cycle, nothing to do with genuine intentions to stop.

Funny don’t you think that he listens after a heavy loss, when it crosses his mind he might have pushed you that little bit too far ? It is no game, but it is distinctly possible that he gambles also with your relaitionship.
I also believe any active CG will say anything to keep those that in some way enable the addiction to stay alive. Enablement takes so many forms other than financial ones, its often seems like a very complex subject, one which I certainly struggled with.
An example of enablement could be something like keep allowing these fruitless discussions to take place – it can keep it alive, you get manipulated, lied to and he continues to gamble feeling that he has succeeded in fobbing you off (excuse my harsh description). The point I’m getting at is if the same cycle continues, the end result will always be the same. He has a cycle and so do you, it is changing your own cycle, your own response – that gives a different outcome. Different outcomes are also not necessarily the ones we hope for.
So in theory a different response when he does exactly the same thing on his next pay day could be a very short and swift supportive comment from you like
“I am not interested in hearing about this, but do please come and tell me when you have sort help and I will be happy to support you. Also please let me know if you’d like me to manage your money for you and I will be happy to do so ” and then refuse to have the conversation any further, then carry on as normal. Provide no money, pay off no debt and don’t be fooled into paying for everything else yourself.

I am not trying to tell you what to do or what to say, that was just an example which saves you from a lot of the stress of listening to the BS and having another meaningless conversation ! It also doesn’t give a lot to argue about although I have no doubt he’ll try to pick one, don’t fall for it, it feels personal but its yet another tool of the addiction. Leave him to consider his consequences without involving you, you can turn your back on the addiction without turning your back on the person and one thing is certain, the addiction will be confused.

I realise you see cheating as a matter for another forum but I think it is not always a separate issue it can be quite connected – gambling with relaitionships or certainly securing another enabler, maybe if you speak to Velvet in a group she can give you the same insight as she once gave to me on this very subject. Don’t underestimate the power and conniving behaviour behind this addiction.

Who knows what it will take for him to come to the realisation that he wants to stop, leaving him might well at some point be a factor in his decision making process but it may not.

My concern would be more for you should you decide to stay

Keep reading, posting – try not too blow your top, its only going to put you through more upset.

Above all look after yourself