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I would be generally concerned. There are scam operations that are almost exactly like what you described. Scams nowadays aren't quick - some of them take months to set up, and the scammer talks to the victim (often a middle-aged lady) for weeks to months before they start asking for money. It's unfortunate the world is like this, but sometimes you have to be callous to other people to protect yourself. I don't know what I would do in that situation.
Also if you have highly agreeable people in your life and you’re less agreeable, you need to step in and help protect them from being manipulated.