I agree with you, it's not nice when you try to profit of your friends and I would even say that it's not a serious friendship. Gambling is fun and if you are just looking for some action to have a good time, I can understand that, but it shouldn't go so far that you are trying to make money of your friend. This is especially the case with skill-based games where one player has an advantage over the others. In my case I do gamble with friends sometimes, but only with very small stakes that never hurt anybody. During our poker nights we usually have a buyin of 5 USD, which keeps the game interesting and doesn't let you feel bad when you lose. The other form of gambling we have is when watching some sport matches, we like to bet on the outcome for one beer. Again, it doesn't really hurt if you have to pay for a beer of your friend and it makes the game a bit more interesting. I would always prefer to wager for some physical things, like drinks or food then betting money. Among friends’ money should never be an option as it will only lead to anger and could ruin a friendship in the worst case.