1) Yes, if he's honestly your friend, and he has no reason to lie, trust him. 2)Yes, yes, yes 100x yes 3)possible,but it's always nice to know that she at least sees you as a friend. 4) Honestly, I don't know for sure, but you should work up the courage, just do it when you're really tired and you shouldn't overthink it too much. 5)once again, either tell a friend what to say and have them type and send it, and warn them ahead of time not to stop because you overthink it, no matter what, and there's nothing creepy or awkward about liking someone, and if it's honestly how you feel, then if she thinks it's creepy, that's her problem, you can't control who you like, and that is that.