UPDATE:
Went over for dinner a few days back after work. Tension was 'off' in the air, as if she didn't know how to handle our situation. She was waiting for me to make the move. I didn't and we just conversed and ate.
I was a little disappointed that in our entire time hanging out that time she didn't bring up her work (journey/introspection) at all. Made me realize that I need to let go of wanting to help her. If she wants it she will go for it. "You can take a horse to the river, but you can't force it to drink".
We did have an interesting conversation on chivalry and paying for dates...
We chatted about how women get a bunch of free things and taken care of, but the guys always get emptied out. Chatted about modern day etiquette for dates, and how it is so skewed in the favor of the women. Then delved into whats the reason for guys having to pay, and how come women paying for men is seen as a "douchebag" move on the guys part. I conversation went a little like this...
Her: Guys should have to pay for the dates.
Dude: How come?
Her: It's the correct thing to do.
Dude: Why? I would pay for my gf, but not for a person I don't know.
Her: Ya, I would pay for my bf sometimes too, but you should court a girl.
Dude: Women are at a place in society where they don't need men's financial help, so paying for a women is almost like your actually paying for something else.
Her: Not really, your just showing a friendly gesture that you like her.
Dude: Why would a guy have to pay to be nice. There's other ways to be nice. Why should guys pay?
Her: For good head.
Dude:
Uhh
Her: No, but its the right thing.
Then I go off into saying that it sounds like its not too far from prostitution and men are practically paying for sex.
In the end, the conversation moved onto a different subject, but I was happy this came out.
To hear the words actually come from a female, made it that much more potent.
Reality doesn't lie.