How should I handle this situation?

[Phenomenon]

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I just woke up this morning and found his note that he won $1500...and hes asking....can I stop over later today for the money? How do I handle this?

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Your response should be to ask him for an additional $500 to add to the $1500 so you can freeroll on his 2k for a night in repayment for your kindness, as you had done for him in the prior night.

At the end of the night after you are done playing, you can then repay him the $1500 if theres any left. If he doesn't go for this, then it shows he was taking advantage of your kindness, and thats not a friend, it's a predator.

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I actually love this idea, good stuff.