A Brother's Obligations: Ask Noah

NEW YORK (TheStreet) -- Q: My brother and I have always been close. As adults; I have become financially successful and he has struggled. He has often asked me to lend him money for a variety of reasons. I've always felt obligated to him and have loaned him the money.

Recently he asked me to finance a project of his as an investor. I am very wary of this plan and feel uncomfortable investing. I would like nothing more than to trust him here, and yet my discomfort reigns. Please advise me on how to proceed.

A: The financial generosity is admirable.

However, it is creating an unhealthy family dynamic and cannot continue in it's present form.

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This "unjustified" obligation toward your brother is breeding "justified" resentment. "Investment" in his projects brings with it obvious concern.

You've mentioned confidence in your current financial status. Circumstances change quickly these days. Protecting your own net worth is still a factor.

You must be fair about your role in this exchange. You have free will, and have been writing the checks. Yes, it was out of love . . . . However, it has created dependence.

An honest discussion with your brother is needed now. And you have to accept that feelings on both sides may be quite intense . . .

Will he or you feel guilty? Will he or you get angry? Will he or you be apologetic?