Losing money when gambling is already a major risk because the comparison of experiencing defeat is much greater than getting the victory. If we realize that it certainly will not hurt.
Taking steps to continue the game even though you have won is much more painful because the decision we made to continue betting did not produce any results, in the end all we get is regret, the money that we have clearly obtained cannot be owned, it is all gone, nothing is left.
OP's thinking is simple, losing gambling while using money that should be used for daily needs. Or, almost winning a lot of money, but take a risk to not to making a withdrawal until losing everything because continued betting.
In my opinion, the most painful is the first one. Because it is mentioned that using money to take risks, if the money is not free money, then he will be regret and feeling pain because that are allocated for daily needs
(for example) , but because he was taking a risk with gambling, unfortunately he loses all of his money. Almost winning and losing, this can be interpreted, even if you lose it doesn't matter, because there is a money saving for shopping or daily needs.