Nothing is more hillarious than when you get all your roomates together to pay the rent and one guy is like, "Oh shit, I have $0" and so you all gotta cover for him! Especially when he resigned the 9 month lease with you NOT EVEN A WEEK AGO. What a roomate!
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Has anyone ever taught him how to handle money at all, btw? Maybe that's all he needs. Once you do something dramatic to a friend like this it's pretty hard to be like how you always were (I know this from experience.) You could always pay off your debts eventually. (Unless you get bad credit then you're marked.) All these are just third party suggestions. You guys are the ones who have to live with him.
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