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The feeling will be different if it is your first time gambling and you win, and another experience if you have been gambling for a very long time and then finally get to win.
For the first person, the first winning will be met with more excitement since the person has not lost to gambling. That excitement often leads them into gambling more.
For the second person in the second situation, their excitement will depend on the amount they have won. If it is an amount of money more than they have lost, the celebration is usually bigger than when it is an amount of money not up to what they have lost to gambling.
Yes you are right, when gambling and have been losing for long even where there is winning and the winning isn't equated to what they had lost for long term it wouldn't attribute anything to them rather is just a part of what they had already lose on their gambling period. And the other case, winning is like drawing them into gambling the more because they have just tasted the sweetness of games hence, they would always think that winning in gambling is always that possible for them.