Well my friend, you are in a tight spot indeed.. Look, I have been in the position of asking someone out that your friend likes and asking someone out that is very close to you and you don't really want to risk awkwardness..
Let me tell ya!
DON'T SWEAT THE FRIEND! The best thing to do is just tell him straight up whats going on, if he doesn't like it and acts like an ass over it nothing you can do. Don't try and live for other people, you gotta fight for yourself..
Now for the girl, and this is the damnably tricky part.
Look, if you really like this girl then not telling her is just going to lead you to depression and will cause awkwardness because you will have other things on your mind. If you tell her how you feel, and she doesn't say yes its the same deal, but you will both get over it quickly. But if you really feel like she was dropping hints then odds are she was. Just make a move.. And honestly, don't sweat being bad with words; EVERY GUY IS! We where all stuck when we where asking our first girl out. Its hard, awkward, and it takes a lot of balls.. But hey, if you are already willing to post it out on the internet it shows you have them already! So go get her!