Unless I'm talking to friends or other older guys I never bring up my age on a session (unless someone asks).
But still, I'm not bothered by people who do, not because I think it's cool or necessary, I just understand what they're going through.
It's a hard pill to swallow accepting that you're past your prime and you'll never be as good as you once were at your favorite thing in the world. Especially since skating inevitably becomes such a big part of your life and personality.
The whole "old guy doing my best" comes in because people don't want to say "I just suck at skateboarding and that's all there is to it", especially when they were once much, much better than they are now.
I love it when people can successfully age gracefully, but I have empathy for people who struggle to do so.
It's not always easy for me either.