There is no reason for someone to borrow Christmas money this early in the year. He has plenty of opportunity to get apart-time job.
What is his possibility of working another job?
I think you should only give for necessity purposes. You should make a short list of good money management principles for him and recommend some books.
I would tell him straight up, that you think he needs personal finance education and that you will help him with knowledge, if he requests it.
I have two brothers that are unwise with money. I've been nicely giving them books and indirect advice. I wish someone had conveyed to me years ago that I could do much better with money, than I was.
Don't help him nicely on the surface, challenge him in a deeper way. I e-mailed my oldest brother and told him I was concerned with his approach to personal finance. I told him about my transformation and the good benefits that come with learning and sacrifice.
Personal finance has been such a handsoff subject between people and families. I try to break that ice the best way I can find, but staying silent leaves me with guilt.
If he rejects your attempts to help him with knowledge, he will understand why you will not give and you will have done all you really could do.
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