windows live mail not leaving my outbox

I use Windows Live Mail, none of the others seem to be talking about windows live mail. What happens is my emails are just sitting in an outbox instead of going off my computer. I think this happened when I tried to send a pdf from the file itself rather than as an attachment and I think I may have messed up the email paths that they take because I answered yes to a question I probably should have investigated more. Is anyone else experiencing this? I have no idea what to do or where to start.

<Moved from Bing>