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Check/calling the turn is SO WEAK here.

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I am confused. If I think he has the flush and he lays me the correct odds to call, then isn't raising a mistake because the extra money will be going into the pot when I am behind after he has allowed me to make a profitable call?

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check-calling the turn is fine. he could only have the flush or air. there's no way a worse hand is calling a check-raise. where you misplayed your hand was the flop. pushing wouldve been best but i guess you couldn't push b/c of the 500 dollar state law... so you shouldve just called the raise and kept the pot small on the flop. bad re-raise to 550.