What a fantastic question lil, and a wonderful response from your friend.
That to me is a big part of why being older is easier. You realize that all of your insecurities, fallibility's etc. are shared in everybody else. You know that even the most seemingly-confident people are just as scared as you are. You know that even the most beautiful people think they're ugly sometimes. We are all a bunch of weirdo's :) I think it gets much easier actually."I can't say I know more than I did back then, but I have more experience not knowing it."
-that's a very good synopsis of what I've experienced. I have mentioned this to you before I think, but one time when going to a funeral of a close family friend I told my father that I didn't like the idea of going because funerals are always so awkward. I asked him "dad, does it ever get any easier, any less uncomfortable?" He replied, "when you are older you realize that everyone is uncomfortable; it's not just you."
and now I've actually met your wise dad face to face - I mean really face to face, not just google hangouts f2f.