I don't want to give too many details. I just wondered what your thoughts would be on this exchange.
Her: Oh I'm not sure I have anything suitable to wear.
Him: Why don't you wear that dress you wore before. You looked really good in that
Her: Dress I wore before?
Him: Yes. That black dress you wore for (some details were given but I'm not including them here). You looked really good in it.
Her: I remember! Wow, I can't believe you remembered that. It was nearly three years ago!
Him: Well, you looked really good in it.