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Surprisingly, actually a couple of legitimate answers there.

Unsurprisingly, a poorcel is replying to all of them with his imaginary knowledge of how upper class people operate.

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Rich people can usually smell a poor from a mile away.

I don't know why poors think they're able to fool us.

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Indeed. Which is why I think the 'become a tennis coach / golf caddy' advice is the only remotely feasible option.

It still won't work though, because he needs to demonstrate value and charisma to get some boomer to take a shine to him and tell him how the world really works, but I doubt he's capable.

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