Usually when i ask the boss a question that brings his authority or competence into question i try to phrase it in such a way that it doesn't sound like i am questioning his sanity. First thing, if you say anything wait till you have a chance to cool off, and i do not mean that in any negative way on your part. I don't want you get fired. In your line of work you might try asking your boss how he decides who gets the prime real estate out in front and who would wind up with the table in the alley. If you need to explain it further i would not mention any names, just say that two long time customers came in a few nights ago and one was seated in the alley and the other wound up out in front. Just wait a while till you can ask the question and keep a calm mind. From your description so far, Mr. Tom was a single on a busy night and your boss decided to put just one patron at the table in the back instead of several.

BTW, Pete the rest of us are not pretty and Italian like you.