I'm new here but have lurked a bit and had a topic I wished to discuss, or more so a problem I needed help with.
I've only really been into game for a couple weeks but I've approached many sets and women, one problem I see myself having is "Overplaying my hand"
By this, I mean that I perhaps think I'm doing better than what I really am. For example:

Last week, in a bar smoking area.
Talking to a girl I used to see when i was like 13 (we made fun of how strange it was after seeing each other after so long)
She came over to me and asked "So XYZ, how's life been treating you?"
To this I looked her dead in the eye and said "Fuck off XYZ, after all this time you want to come over and start small talk like a normal person?" Of course I did this in a humorous tone with a smile on my face.
I then took this as an excuse to, as i literally put it to her, "elevate small talk to medium talk."
She laughed again and when asked what do I mean by such I said "What is you're biggest fear in life."
She was taken aback I think by the straight up approach of something that would usually be given a more serious manner or perhaps by the strangeness of the interaction in general.
Chit-chat continued for a long time, we were together for a portion of the night. At one point I was even able to tell her I knew she had a boyfriend by the fact she had no earrings and nailpolish so she obviously wasn't looking to pull.

Blah blah blah, the point is, I had her in the palm of my hand (or so I think) and it was at that point I decided to leave and tell her I had to go meet my friends again.

To be honest, I'm not sure why I done this.
Perhaps I thought I'd let her chase me and I was being too on the offensive.
Perhaps I thought that her having a boyfriend kept her off-limits (as moral as I am, this doesn't overly bother me, I'm not using mind control and she is her own person to make her own decisions.)
Or, perhaps on some level I was afraid of succeeding? I don't know, I was just wondering if any of you guys had any words of wisdom for me to enlighten this dark situation!

Patch