Local festival LD contact

Hi I’m a 14 year old boy, and I have a internship at a local venue(400 cap) I know an LD who does the lights for the biggest show in the city. I have worked with him once and he was really impressed with my skills om MA3. But since I have only worked with his friend (I’m at the console and he is calling color). Should I ask him if I could shadow him at the festival, would you guys be comfortable with a 14 year old shadowing you? And When should ask it?