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Trying to pull more information from people than they want to share is somewhat rude.
In the context of potentially offering to float cash to a stranger - and getting a vague response about the exact situation requiring urgent cash - I'd like to know whether the person is trustworthy. Finding a mug shot that potentially resembles the cartoon version of the person requesting the cash from their website ( [link redacted] ) I see no harm in asking whether the person in the mug shot with the same name and potentially similar physical attributes was the same person.
Personally, I'd trust somebody with $300 before I'd trust them with my codebase.
If you're planning to spot a fellow HN user some money, and you can't show them any trust, at least show a little professionalism. If you just did that for your own amusement, please don't ever do it again.
Your suggestion that this was done for amusement is incorrect. A basic name search for a person in "urgent" need of money from strangers where no friend or family is able or willing to help seems like pretty basic due diligence to me.
Additionally - I'd refuse to ever lend to anybody that was an active gambler:
"@[name redacted] Hello, do you honor bets where you have made an error with the odds? (Sports book not exchange)"
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The exact nature of my original question was trying to determine what the money was for, and that question remains unanswered.
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