Name three positive letters you have received by certified mail. Okay, can you name one? Neither love letters nor demands for payment called bills are sent in such a manner. There is a high probability Bob will either refuse the letter when he sees your return address or simply never pick it up from the post office. Either way, you will lose another month and accomplish nothing. We only use certified mail if the law or specific legal agreement says we must, and demands for money are not one of those times.
Regular mail works fine. Bob will receive it and will open it. Faxes and e-mail are perfectly acceptable too. If Bob is such a liar that he is going to consistently claim that he’ll the make payment after each monthly request, and has yet to do so, your problems with Bob are much larger than a simple “Please pay me!” I don’t think certified communication is going to get you anywhere and you probably just need to go ahead and take legal action against him.
If you still like the idea of certified mail and believe the addressee might sign for it, send the identical letter first class at the same time, so one way or the other Bob’s sure to get the letter. However, the single best way to insure that someone receives your demand or request is personal service. It is not just for lawyers. Simply search for “Process Servers” online or in the yellow pages. For $25.00 to $50.00 you will have an independent certification that a document was delivered to a certain person on a certain day.
The real lesson in all of this is that loans to friends or relatives are often not loans at all, but gifts; whether voluntary or involuntary. Acknowledge to yourself when you lend money to friends or relative that here is at least a 50/50 chance you will not be repaid and that is OK because the relationship is more important than money. Otherwise, do not do the loan.
If you, the lender, did not get a promissory note from your friend, that is a sign that neither of you believes it is a serious, real debt. Acknowledging gifts up front saves a lot of emotional grief for you; hurt feelings for the debtor; and irrevocably tarnished relationships for both of you. If it is truly a loan, get a signed promissory note. You have something to take to court and the debtor has physically and emotionally acknowledged it is not a gift.