How do I kill the bunny?

I need to get back in the game. I haven't been on a date since December. It's not the ideal time but I'm not going to let a little thing like being jobless keep me from trying to attract women. I mean, honestly, is gainful employment really that high on most women's list of requirements?

I went to get my haircut today at a little place a block from my apartment. Normally I don't talk to the people that cut my hair. I want them to focus on the task at hand. This girl was kinda cute and she was chatty so I talked her up. We had a couple of laughs and she asked me if I had been to any of the bars in the area. I chose not to mention the Hooters down the street where I spent Valentines Day. She allowed as to how she liked to go to the R.T. O'Sullivan's in the same strip mall. She apparently knows one of the bartenders. I took this as a good sign. She insisted I get a wash after the cut and it seemed to take a really long time. Admittedly, I could be way off here but it seemed like she spent an inordinate amount of time caressing the back of my neck below the hairline and my earlobes. My earlobes are a hot spot for me, but I won't get into that. Point is I felt like I was being flirted with. I told her I really liked the cut, tipped her generously, and told her I'd be back for my next haircut. I found it interesting that I started judging her almost immediately. She mentioned that she was married at 19 and has since divorced. She's also a hair stylist which does not impress me and she lives with her sister in AJ. I thought, "She's probably got a kid she's not mentioning."
I've never been one to date for the sake of dating. I know that one person is always more into it than the other and I feel guilty if I'm the one that is not emotionally invested. I think it might be good for me to see if she wants to have a drink just because she might be fun to drink with.

I have also had my eye on my niece and nephew's basketball coach. She is an attractive young lady that is a first grade teacher at the elementary school that my sister teaches at and her kids attend. After one of their games my sister said jokingly, "You want me to hook you up with Coach Monica?" I think I caught her off gaurd when I relpied, "Yes, I do." In a true elementary school move my darling sister mentioned to Coach Monica that I had asked about her. Apparently Coach responded favorably. I finally got an introduction tonight when I attended a school music recital. She caught me looking once and gave a shy smile. I thought it was cute the way her students obviously adore her. I like that she volunteers her time to teach basketball to 5-7 year olds. Also, tonight was the first time I got within conversation distance and noticed that she has beautiful light blue eyes.

My sister told me that I "should really ask her out". I don't think that my sister would say this if she didn't think Coach would be agreeable. I would like to ask her out but I usually like to have at least one conversation under my belt first and each time I've seen her there have been no less than 7 of my family members in the room. I am a little uncomfortable dropping some game when my parents, grandparents, sister, brother in-law, niece, and nephew are bearing witness. Stage frieght I guess. I'm not sure how I'm gonna pull this off, but I can't wait too long or she'll assume I'm not interested and start dating someone else.

In any case, I can't imagine how me writing about my misadventures in dating could be anything but entertaining. So, I'll keep you posted.