I am sure he will

And what I thought was stupid and small at age 5 I may now look at and think that that it's a valid and understandable concern, or that perhaps she's got issues with her standards on herself, or her desire to be included, or her wish to impress someone in particular ...

With your son, naturally you're going to know him best, and probably be in the best position to make him comfortable and confident enough to confide in you about what is going on for him, which then will enable you to determine what (if anything) to do.