Even though you gamble almost every day, you should never aim to get back the money you lost before. Because if that is your target, then you will only get depressed and make your gambling a burden which will certainly not be good for your finances and life. So, even if you gamble almost every day just make it fun by playing games that you like and also with money that you can basically bear if you lose. But even so, that doesn't mean you just play randomly, because gambling is basically targeting victory, but if you have a good foundation then you won't be depressed when you lose.
Gamble every day will potentially makes him becomes addicted to gambling if he can not control his minds. And that will be more risky for him if he wants to recover his losses because that can make him spend more money easily.
He need to know that when he losses his money in gambling, he must stop gambling and not continue gambling or even trying to get his money back because that can makes him lose more. Losing in gambling is usual because gambling itself is not a place to make money. So when he can consider gambling is a place to have fun, he will not lose too much but that still under control.
He can still playing gambling every day but he must have a strong control for himself so he will not get tempts from gambling.