Ask Emma

Question: I had a business lunch with an older man, whom I know through friends, and who really likes me, I think. He paid for a nice lunch, and then he stopped a cab for me and gave me a $20, saying, “All you owe me is the change from this.” I’ve got ten dollars change from the cab. Should I mail him a 10-dollar bill or wait until I see him next time?
Answer: Under no circumstances should you put cash in the mail. Sending a check would be an option, but not without the consent of the second party. What you should do is send a nice Thank You card briefly letting the man know how you enjoyed the lunch and how quickly you reached your destination in the cab. After your signature, put in the P.S., “By the way, I have a ten dollar change from the cab. How would you like me to send it to you?” In this case, he’ll have an opportunity to request the check, to refuse it altogether, or to use it as a reason for another meeting with you. That is if you want to see this man again. Otherwise, just mail the check.