There are a number of social, emotional, and/or psychological issues that appear to be part of your question. For this, you may want to consider reaching out to a mental health counselor, psychologist, or other appropriate source of support in your community. As for the financial question about whether or not to lend your friend more money, eXtension has long cautioned about lending money or cosigning loans for others. It is very risky and can endanger both your finances (if debts are not repaid) and your personal relationship with the borrower. This advice especially applies in your case since you are already owed $2,000 on past loans.

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