There's a friend I want to get closer to, him and his group. But I'm so anxious

I wonder: what if he thinks I'm annoying? He's a busy guy, like me. We have so much in common, same humor, same extracurricular (orchestra), and our overall beliefs and values align well. He's a really cool dude, and I see him with his friend group, and I think that they all are so cool

Here's the thing, though. I message him a good amount, probably a convo every other day or so on average. But I always start them, and while he vibes along really well, I just wonder if I annoy him by texting first? And the thing is, while I talk to his other friend group, I don't have their contact info so it's mainly him and I'm scared they'll think "who is this rando trying to talk with us." I just think they all are so nice and we'd get along well, but Im so worried, idk how to get myself closer to their group but I want to try.

I'm scared, but I want to ask if I can sit with him and his friend group at lunch, maybe message him? The thing is I'm an outgoing person, I can talk to almost anyone, I know a lot of people.. but I still get so anxious when it comes to people I admire.

Should I ask him? How do I message him asking??? How do I not be awkward

I'm outgoing, yet so awkward at the same time. I hate this feeling.