Backround: I co-host pickup basketball events in my area. One particular female signed up to play and played on my team. After the 1st game (there are 3), she felt discouraged (felt that she was holding the team back), and I convinced her to stay. She stayed and scored a few shots. In fact she did fantastic. She gave me a hug at the end of it. (on the actual date she told her man how I encouraged her to stay and how she scored)

2nd time, she showed she was on my team; we had good conversation (shared a few likes, i.e. theatres, dancing) and we had good rapport. At the end of the game we exchanged numbers and I set up a day to meet that week that she agreed upon. In fact she recommended drinks.

A day and a half later I texted her the spot to meet and the time.

Here are the details of that date night:

I met her 6:30ish at the bar, I arrived there first; she came a few minutes later.
Some chit-chat about the ambience, etc. ordered sangria, chit chat some more.
Give her some Dhv stories about my life (i.e. me hiking thru the Andes Mountains, etc.)
I did some kino with her: play some thumb wrestling with her; I read her palm to guess her age and I guess right then give her a high 5 (She’s twenty-eight) all with the intention of building more comfort.
There were no lulls in the conversation at all. We even shared drinks…(I would say we were there more than an hour). At the beginning I casually told her I’d get the 1st round as she walked the most to the location. When it was time to pay the bill she paid for all of the drinks and said I’ll get the next round.

While walking to the 2nd bar we were still chatting. I kept in mind that I had to kiss her at the very least at the 2nd bar.
At the 2nd venue we ordered more rounds and I found out more of what I sensed about her persona-that she is insecure.
e.g. She told me her longest relationship was 5 years and her boyfriend was gay and really hasn’t had a steady relationship (one relationship lasted 5 months). And she was iffy if she was going to her high school reunion this past Saturday.

As our conversation progressed there was light touching from the both of us.
On one occasion I gave her that look (I want to kiss you look). I get a sly response from her of “Why are you looking at me like that?” In retrospect, I should have gone for it right then and their, but instead there was a distraction from the bar and it prompted her to go the bathroom…Big mistake on my part for not making a move asap. 

She comes back and the conversation keeps flowing. The subject of dating comes up.
She asked me do I date. I reply “Of course. I date quality girls.” I ask her in kind
What qualities do you have? (Too much of a big hoop to ask) She couldn’t answer. In her words “I’m not sure how to answer that.” It seemed like she didn’t know what to say…

I asked her what she thought of me. She described me as confident & cocky. And several times, throughout the conversation, she kept saying I was interesting. In addition, she said I was deep and profound. There was a point that she said that she’s not used to compliments.

She wanted to hang out but when I whipped out the phone to pick a date she wasn’t sure when she’d be available next week. In my book she wasn’t ready to commit just yet or just didn’t want to seem easy. At the 2nd venue we were their for about 2 hours…

On our walk to the station I gave her the first kiss on the mouth (albeit a light kiss)...she asked me to behave…so I kept on talking like it was nothing...etc...chit chat…Their was still a comfort between us as our shoulders were rubbing together on purpose.

On a side note I noticed she doesn’t like the cops and she told me that she’s dated 2 which I suspect ended badly for her.
At the station I kissed her on the cheeks and mouth and gave her a hug-no biggie. She said he had to go as her train was coming and I replied playfully that I had to go sarcastically.

Ok guys, my aim is not to focus on this one exclusively as there are so many beauties in my fine city. What I want with this one is to keep her around by reminding her every now and then that I’m a “cocky and confident” guy that uplifted her spirits. So by Day 3 I want to seal the deal with her or make out with her hardcore. I ask myself this question though, how do I keep the momentum going with a not too confident 28 year old girl (i.e. In thinking back of day 2 I may have come across as too confident for her to handle)?
In addition, we work in the same city but she lives in another part of town; so commute is an hour for both of us.


What I have done since then:
1. That same night I shot her a text asking her if she got home ok? <No response>
2. Two days after that I left her a vm saying that I’m about to leave to go out but wanted to give me a call. <no response>
3. Yesterday I shot her some texts to let her know what I’m doing this weekend. I have a cooking class with a few friends this Saturday night. Her response was “never done it but sounds cool.”

If nothing happens this week..no biggie.

Considering I know her schedule somewhat this week, (she doesn’t know what she’s doing this week what do you guys suggest?

Thoughts?