I taught middle school, and braces were really not the big deal they were when I grew up. It seems everybody has them, and the kids really get into picking different colors for the bands each time. All kids feel self-concious in general in middle school - it's just the stage they are in. Remind him of what he is good at and that all the other kids feel insecure too. He doesn't have to have a BFF in order to have good classmate friendships. Some boys really are just floaters - fit in with many groups, but not really personally connected to anyone. It took my oldest son until 11th and 12th grade to really develop some strong friendships, and he is a kids who is friendly to everyone.