How to be more outgoing and talk to that guy.. :) ?

[Jessica]

I hate being shy. :/ Next year is my senior year and I want to make the best of it. I don't really have any friends other than 3 and 2 of them are graduating this year. I want to be more outgoing and happier with my life, but I have been shy my whole entire life. I can never think of things to talk about to new people and I really want to have a date my junior and senior prom, at least my senior prom though. I have this huge crush on this guy, we've hooked up when I was drinking one night just makeout nothing more, but I don't know how to approach him :/ We talked in July then after that he got a girlfriend, but his talked to me on facebook not that long ago, him and his girlfriend broke up but they are still friends.. he actually said something to me today defending me sorta against an asshol* i just don' t know how to approach him again. :/