First off, tell your friends you'll handle it from here, thank you very much, and get them to stop passing messages back and forth. That's grade school behavior.
Second, invite him out for soda or coffee or whatever you prefer to drink that isn't alcohol. Just, come and let's get a coffee.
That sort of thing. This is not the time to confess deep feelings. Put that on the back burner for the time being. Instead, have a conversation. Not about dating or feelings. But about what you like to talk about, whether it's music, school, the news, the weather, or something else. Try not to make it about anything gossipy (because that's mean).
When it ends, tell him you had a good time (but only if you did) and ask him, "How's about we get together soon and make it a real date? Say, next weekend?"
And see what he says. If he says yes or no, then you have your answer. If he hems and haws, then give him a week to figure it all out but move on if he can't make up his mind and/or tell you either way, for that is also a no; it's just a more passive-aggressive one. And of course if he doesn't agree to go for coffee in the first place, then that's another no.
This is 2016. You can do this.
Be the initiator and you will not regret it. You will know, plus you will build confidence. Being the initiator in this area will help you in other areas of your life as well.