He has more issues than Vogue I´d say, and his behavior is quite off pushing. He felt comfortable at your place during his first stay, and that has given him some confidence and trust. If you are not comfortable with any of his behaviors, simply reject his inquiry, and do everything through Airbnb. Your message shows that you are not comfortable with that, so don´t mess with your peace of mind.
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I’m definitely stealing this one! 
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In case anyone was curious, this guy disappeared as quickly as he reappeared. He sent the message about how he wanted to stay again and then never responded to any messages after that. He has burned this bridge as far as I’m concerned, but that doesn’t change my curiosity about what’s really going on with this guy. Guess I’ll never know.
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Be my guest, Emily! It´s a nice way to say that one is very problematic.