Dude!!!!! Im liking your frame of mind!!! PLEase Reread your last 3 posts whenever you feel down about or are over thinking your situation. Apply that Mindset and you will have success.... Guaranteed!...
I agree with what you said:
"New me is going to be "I don't really give a fark, let's have fun we are young" Then if something happens it happens. I am just going to pretend like I am a player and in turn maybe I will become one. Usually I am embarrassed, shy, or scared to use the techniques I know such as push pull and etc. fark it; what's the worst that could happen. Especially with her. I am already in the friend zone the only thing worse that could happen is her not wanting to talk at all which is her loss. "....
This is perfect!!!
Also, I think its better if you bring your two buddies, or one buddy. This way you will have some social proof and can always have your buddies dhv you and attract a crowd which you can work off of. As well as provide a ride and allow you to drink without worrying about driving. Also, I agree on NOT taking the train in Chicago. Ive been on that thing when I was there and it was definitely not the safest situation. So, take your buddy/buddies. Just have a good time yourself and don't worry so much about HER, and she will follow your lead.
Your gonna be fine bro.. Good luck and just have fun!! also, don't worry so much about your living situation or money situation. Take her home to your parents house and do it there. Cover her mouth with your hand. It will probably turn her on. If it bothers you it will bother her. If you don't give a fuck, you can live in a dumpster and she'll be fine with it..... Cheers