My dad is scary good at blackjack. He'd gotten kicked out of a casino once because the dealers were convinced he was cheating.
I tend to be a very unlucky person, so when I gamble, which unfortunately I do far more often than I should, I make sure I know how much I can afford to lose whether it's money or not and don't allow myself to go past that amount. As far as winnings go, I usually stop at a profit of about $10-$20USD depending on the game. If I'm feeling antsy I go until I start losing large amounts just so I can walk out with a profit.
I still have a bunch of chips I need to cash in. That's some $50 I could really use right now.
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