Basically look at it this way. If you can't convince a federal judge it happened the way you say things happened, then it didn't happen the way you say it happened. If you loaned money you should have a written agreement that would be legally recognized in your county court, so that you could enforce the terms of the loan if it came to that. It's my suspicion you're posting here on hypothetical situations because you don't want to reveal what you are really doing. Makes me suspect something that may not be legal and you know it. We are not lawyers. You may find it better to seek the services of an attorney, or even a tax attorney since in many cases an attorney is bound by client-attorney privilege.
