When you are going out to gamble a bit then you are going to think about winning because that is the reason why you are going but when with friends it can also be fun even if you lose.
But it is way more fun if you manage to win with gambling.
Most of the time when you gamble with your friends you will lose because you cannot concentrate as you will just bet base on your emotion, it is good in a game where strategy is not important and if you are lucky you might win but still you will not keep that money because you are still gonna enjoy that spending in other things.