Is it ever appropriate to tell someone he or she must have been great-looking back in the day?
A) It all depends on your relationship and how exactly you frame it. B) No. Period. C) Maybe. It can be done without implying that the person looks awful today. D) The real question is why would you contemplate saying something like that? E) The problem is there is no way to avoid sounding as if you believe only 19-year-olds can be attractive. F) You can't know how someone will take that. But it's almost worth risking it on the chance the person will get a kick out of it and say, “Yeah, I would have been way out of your league.” G) Other.