I use to do this more in the past than I do now, but I have loaned a couple of people some money. They were not friends, but just rather acquaintances from the casino. I remember I once gave this old guy $30. I didn't even know his name. This was years ago when I was young. After I did it, I kind of regretted doing it since I hardly knew him. He did pay me back. This was back in the day when min bet was $2.
Years later another person asked for a $100 and I loaned it to him. Again not a friend, just a casino acquaintance. I did get paid back, and he did ask for money again several more times which I said "no" to.
I also use to give money if someone didn't have enough for a split or double down especially if it was a good double like a 10 or 11 against a dealer 5 or 6. I would say if you lose you don't owe me anything and if you win just pay me back. I would expect payback right after the hand if they won and if they didn't pay back right away I would call them out on it. I very seldom do this now days. I figure as soon as they lose their money and leave, I will have better playing conditions. At times I do want another player at the table. However, many times I see folks step up and offer money for the double if the player doesn't have enough especially on small bet amounts so I'm not the only one.
One of the last times I offered money was when a player had a good split and a fairly large bet out. I'm not sure what the hand was, but it might have been a pair of Aces against a low card. I don't remember which casino this was at, but I offered splitting the whole win as sometimes one hand loses and one hand wins. Then the pit boss says you can't do that. You can only give him money and then he can just pay you back the money if you win. I said bullshit, I'm not going to risk money without having a chance to get something in return. I didn't give him the money and he couldn't split. I don't remember what happened then.
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