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The story you tell I know very well, but from the other side. I have recently began trying to stop this repeatable process. I really simplifies with the situation that you are in.
The main thing that gets to me is when you break down how much further the two of you could be, How much more things you could have and the holidays you could have been on. Recently I watched the strongest women in my life break down all because I wanted to bet on a stupid football match. Try and just break it down to him, when you are gambling big stakes its easy to lose value of money. In the mind of a gambler they see this as an investment and not necessary in just money but time. Boredom can almost become crippling to someone who is always entertained.
1. Let him know that gambling is not his friend and that he should HATE it.
2. Break down finances and what you could have done with all that money.
3. Talk him through how this makes you feel. (Be it in person or message).
Good luck in this process, fingers crossed for you both,
Charlie.