If I recently gambled away my whole retirement, I owe over $100,000 in debt, when should I file for bankruptcy?

Bankruptcy? How about a guardianship because it seems you're incompetent to handle your own finances.

Many factors come into that question, and this site does not permit of very long discussions. You should definitely retain an experienced Bankruptcy lawyer to advise and represent you. All other things being equal, you might want to consider filing sooner rather than later. But a lawyer can review with you all the facts and factors relevant to a decision and advise you best.

Based just on the information you provided, I do not know if you should file bankruptcy. Bankruptcy is not the solution to every financial problem and bankruptcy does not eliminate every type of debt. For example, gaming markers are treated as bad checks and you can be prosecuted criminally even if you file bankruptcy. You may not be able to eliminate any recent debt you made, especially if you took on the debt at a time when you ought to have known it was impossible for you to repay this debt. Many people believe that if they cannot pay all their debts, that they must immediately go into bankruptcy. Sometimes that is not a solution at all. An ethical bankruptcy attorney will give you an honest assessment of your options.

Meet with a lawyer face-to-face. Your question has a ton of nuisances. Offer to pay the lawyer his or her hourly rate for a one hour meeting. Now is not the time to skimp. A lot of traps await the unwary!