All the personal messages I send are stuck in my outbox with a red icon next to em, the dont show up in my sent messages. does this meen people arent getting the stuff im sending?

Here is the way Personal Messages work. I type a message to you and press send. It is then placed in your "OUTBOX." It will remain there until the person you sent it to goes to their Private Messages and clicks to open it. At that point when it is opened it will show in your SENT items.

So you've sent them but people haven't read them yet.