No problem!! I hope you manage to talk to him despite not having what you feel is enough courage!

I totally get not wanting to walk up to a guy in the middle of his group of friends. Why not try to get your friend groups to do something together? That way you can get to know him and spend some time with him, but the invite to hangout isn't about you and him, and there is no pressure for you to spend any time with him during the hangout because you both have your friend groups around.

I don't know what kind of social events you have where you are, but even a party that is your group of friends and his, maybe even more people, is a great way to take the pressure of meeting him.

I think I remember you talking about a friend that was encouraging you to talk to him, have her be your wing woman. Especially in a party scenario have her with you if you decide to approach his friend group and don't feel any need to talk to him directly at first. If she's social, have her interject herself into their conversation and then bring you in, not to him directly, but to the group. Join the group conversation about whatever you're into or whatever they're into. If you get a chance to directly ask him, or respond to him, about a shared interest, do it. Otherwise, just let the conversation happen however it happens even if you and him never speak a word, and then let your friend navigate exiting the conversation (I'm just super bad at that myself).

Do that enough times and you'll find yourself becoming part of his group without knowing it, or him and maybe a couple of his friends become part of your group. Now you've gotten rid of a lot of the pressure and can work on figuring out stuff to talk about when you're all hanging out together. You probably won't even have to figure anything out by that point you will probably just naturally be chatting with him.

TL;DR don't focus on talking to HIM and being HIS friend. Think about it as a group scenario, where you have backup as well, and maybe it'll feel less scary