It all depends on the person. There are people I know that I would not lend $20 to unless it was a life or death kind of situation and expect that money to be gone. However I have a couple of other friends that I would and have lent to and borrowed from for multiple thousands of dollars for very frivolous items, including gambling and vacations.
With those friends it is more often the lendee that recalls the debt, many conversations of " here is the $300 I owe you" and the lender responding " when did I give you that?". Of course that is years and years of friendship, starting with $20 loans and building up a 'credit rating'.
Based on your comments of him living paycheck to paycheck and being an idiot with money you did make the correct choice.
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