When Will I Stop Shaving My Legs?

I first shaved my legs secretly in the bathroom in the 8th grade. It became a weekly requirement in 9th grade until today. Sure, I have my moments or weeks (especially in winter) when I neglect shaving but if a skirt or shorts are involved, I'm always going to shave.
I went to see a play with my mom a few weeks ago. She wore a cute summer dress and didn't shave. I know my mother so I knew it wasn't something she forgot. She's 50-something and she could care less about hair on her legs.
My question is, at what point do you stop caring about the people staring at the hair on your legs?
Is it different for person to person? Or as you get older, do you start to focus more on what makes you comfortable and less about what people are thinking?
Because in reality, I don't shave because it makes me comfortable, I shave because of the fear of someone noticing the fur.