So this is a person you've known ~1 year who you are "super close with" and see it as a "bro/friendship", yet you call him a stranger?
...
Sorry to say but it seems like you have more issues than this dude who "could be" making poor jokes or "could be" emotionally manipulating you into giving him money.
Don't give him money, sure. But don't ruin a friendship because of an assumption.
Sending money to practically a stranger
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So this is a person you've known ~1 year who you are "super close with" and see it as a "bro/friendship", yet you call him a stranger?
...
Sorry to say but it seems like you have more issues than this dude who "could be" making poor jokes or "could be" emotionally manipulating you into giving him money.
Don't give him money, sure. But don't ruin a friendship because of an assumption.