U2387, it sounds almost like you resent this girl a bit for having fortitude and courage that you didn't, in putting herself out there, and if I'm reading that right (admittedly, I might not be), that's really not fair to her. When you say this:
it sounds like you're punishing her for your lack of balls in the past, and that's...not nice.
That said, I do understand just not feeling it with someone (although I question if that's fully the case, or if it's some misguided punishment, as I said above). Coupled with this is the potential awkwardness and complications you might experience at work due to working with her (bad) and her relative being your boss (worse).
If you're *really* not feeling it with her, I think the kindest thing you could do is to spare her feelings by bowing out gracefully. If you think an "I'm just not that into you" is too harsh, tell her thanks, but you're interested in someone else at the moment.
No, you are not being harsh at all.
I need brutal honesty from people. Its not like I have a lot of experience here, and you correctly pointed out the line where I said myself that my attitude on this is unhealthy and burdened with a significant amount of regret.
I don't want to punish her for my lack of balls, and maybe if my attitude leads to that kind of feeling, it is secondary to 2 things: First, I just can't see myself with her. She is way out there in a lot of her views on things and though she is cute, I do not feel too strong of a physical attraction toward her. Second, as you mentioned, I work with her and her brother in law is one step down from the owner of the company in terms of level of authority over me.
I know I will see her again, go on a date, or a get together or what have you. I would like to do that and then just bow out gracefully. I think that may be a viable option because she is going back to school in a few weeks and I am trying to figure out what to do with the rest of my life- career wise and relationship wise. I just don't want to start anything now and wind up hurting her, as I think she is a unique, intelligent and caring person. I am 23 and she is 19, we are at different points in life and will soon be pretty far apart geographically as well.
At this point, I would like to try and see what is out there for me in terms of meeting girls and working through the interactions from the start to build up a potential relationship. I have (some, and its relative of course to others) new found confidence and I want to try and put that to work and build up slowly with these things.
Just as you suggest:
I'd tell you to call the girl you met at the concerts, and I'm sorry if this comes across as being harsh, but judging from the tone of your post and particularly the part I quoted above, I think you probably have a little work to do before you date or pursue a relationship with anyone. I think part of you probably recognizes this, hence your admission that your attitude is "unhealthy."
With her talk about not wanting to f up again and always telling me about her ex and other "creepy guys," I see this girl as ready to jump into a relationship right now, which I certainly am not.
I honestly do not want to hurt her and I certainly do not resent her for being forward. I actually quite admire that in someone, especially being a 19 yr old girl with a 23 yr old she is attracted to. I strive to someday be more like that myself.
As you correctly observe, I am not ready for a relationship now. Meeting people, flirting, getting numbers, dates, sure, but not a serious relationship.
The high heels-wearing, facebook messaging, pizza dive girl of my imagination is very secure, and she'd shrug her shoulders and go "eh, whatev," and move on to someone without issues.
But yeah, you're probably right.
That would be true if she wore them on her own. She told me in the facebook message that she wore them because an older, more traditional woman we work with suggested it and her friend raided her closet of everything else the night before.
She is not a girl who I ever expected to see in heels, and she said as much.
It was a bit strange, especially when I had flip flops on ! I thought it would be a group gathering, or a casual get together and not a date, so I just got out of the shower and put on my usual not at work summer shoes.
Its not like they are old navy plastic, they are the more substantial brown ones you see a lot of guys wearing, and I had a polo and nice shorts on not gym shorts, but still.....
. . . confidence and 'niceness' can exist in the same persona and is incredibly attractive . . . just sayin' 
Then she takes the check, wont let me see it, gives it to the waitress w/her card. I protest, and she says " I asked you, I'll pay." I responded "I got next time, then." She says "you have to ask then." I was shocked but said nothing. Manipulative much? I didn't even know it was our 1st date, and she has a cooked up in the middle of the night scheme to get a 2nd date??????????
Did you notice how all of the women just totally brushed by that comment?
