Ok, this last week has been very up and down. One night I went out to have a few drinks a local bar with some friends. I make eye contact with this HB 8 and she is obviously looking my way, so instead of getting right up and talk to her, I tell myself maybe she wasn't looking my way blah blah. I ask friends about approaching and all that bullshut, and she loses interst and I let her leave. Blew it.
The next night I went out, saw a girl look at me as I walked in like I owned the place. After a few shots I went and said fuck it and and approached her and her fat friend. Little small talk, didn't seem to go anywhere, so I excused my self. Less then 1 min. later they come to where I was standing and I # close. Well got a little drunk that night and made a dumb phone call to her.
Tonight while I'm at work the HB 8 comes in sits in my section(I'm a server). She was with a dude so of course I think it's her man. As I was serving them we were flirting and I was eye fucking the shit out of here.
I still thinks it's her man so I never asked for her #.
As there walking out she gives me another look, everyone standing around working with me see's and is yelling at me to go chase her down for her #. Then a girl I work with tells me that was her brother. The girl is in the parking lot and actually does a slow circle and is looking at me in the Restauraunt. All my employee's yelling go get her, I freeze up from all the pressure. Lost the HB. If I would of known about it not being her brother damn right I would of got her # in the store, but chasing her out seemed desperate and needy, then again I probally would of # closed.
Sometimes I talk myself out of approaches by lloking at the negatives of the approach. I know I have some skill but I also know I have many flaws with approaching.
Any advice to what I'm doing right and wrong would be greatly appreciated.

Sounds like you already have a pretty good handle on what your strengths and weaknesses are. You should have treated those two as a set though, and talked to them. You would have found out that he was her brother that way. Learn from it. Don't be afraid to talk. That's what it boils down to. She's obviously VERY interested in you. Which is good. You are right though, that would have been needy and desperate if you had ran after her. But, she'll probably be back in again. Next time, talk to her and get her number.

Also, lay off the drinking when sarging.

And, don't worry about what the people are thinking of you when you sarge. They aren't thinking about what you did or said when they go to bed at night, so don't worry about their opinions when you want to open them.