Q: I recently received an unexpected, generous monetary gift from a relative, in the form of a check. The check, however, wasn’t signed. Clearly, this was an oversight. I’m now in the uncomfortable position of sending it back and asking for a signature. Do you have any suggestions on how to word this to the gift giver?
A: Unfortunately this is an awkward situation. You have to return the check with a nice note: “Dear Aunt Maud, thank you so much for thinking of me this way. I am truly touched, but am returning your check because I can’t deposit it without a signature on it. Again thank you for such a nice thought.” You aren’t applying pressure or demanding a signature with this kind of softer wording. This way Aunt Maud can be horrified by her oversight, sign the check and return it, or write you a new one and send it to you. If she doesn’t, there is nothing further you can do.