^
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. But if you're gambling with money that you need for something important, like paying for utilities, a gift for a child, etc., then of course you'll regret your action when you lose it.
Before gambling, make sure that losing this money will not do you any harm. Then everything will be great.
That is exactly the way gambling should be seen, when I spend my money and watch a movie and I enjoyed it, do I regret it? Of course not, instead I am happy I took the decision to watch that movie, even if I had to spend some money to do so, and when you gamble with the same intentions then there is nothing to fear as you will spend some money in exchange for the entertainment you were looking for, it is only when people deviate from those intentions that they can get in trouble and regret their decision.
If you exceed from that original intention and once greed dominates your mind, the chance that you'll lose control and lead you
to a tough situation where you will keep on asking for more.
Gamblers always have that self-will before they start to gamble, it's just the change in desire that affects your mindset when you engage
that much into gambling, being out of control lead you to addiction.
But same with you, if you treat gambling as part of your entertainment and the amount of money, you're willing to spare is for the
sole purpose of gambling, win or lose you can quit without any regret.