If you are gambling with money that is meant for entertainment, whether it is going out with friends to a bar, a movie or any other, even if you lose every last cent, it will not make you regret spending.
Yes, that's true, there's no how you will be angry at getting yourself satisfied and being fulfilled because you have already planned it out before time, but when the unfortunate occurs, that's where we make the wrong mistake on funds misappropriation for using them to gamble or have fun while they were not meant for such purpose, the objection here is not on gambling but on our wrong actions and steps towards gambling.
Before gambling, make sure that losing this money will not do you any harm. Then everything will be great.
And we must not act being foolish by thinking the gambling we are about to play is very sure for a positive outcome, when we bet and loose, we will not like the shape to where we are going to landed at, there's a way we can always avoid these through caution before taking steps or decisions towards gambling.