Without all the extra background info, I'm trying to familiarize myself with not being nervous talking to women. Everywhere I go now I try to make conversation over anything, small things and just have fun with it. I wanna be able to make it a natural habit to converse with anyone easily. I'm not only doing this with girls but anybody in general to allow myself to get a casual conversation going so it'll be easier when I talk to girls. I'm the type of person that doesn't like small talk.

Anyways I've been talking with more girls and teasing them, making them laugh. Not anything ground breaking but it's a good start for me. Today I saw this girl at the grocery store and she was attractive, the person I would totally like to see myself with. However I didn't think much of it and just went to do what I went there to do. So as I proceeded to the checkout lane she was behind me but she dropped her item right behind me all around my feet... At that moment I just thought to myself laughing in my head how convenient is this, maybe she's more nervous being around me. Now to think of it I should've said something like, "Did I make you nervous?"

Anyways the computer was malfunctioning and we had to move so I teased her that she's bad luck. We began to talk just about anything just making fun of her and the cashier joined in joking around saying I'll buy her groceries and why didn't I give her my Christmas list. It was almost as if he was playing cupid. I would've loved to ask for her number but I just couldn't get myself to do it. I've read about people just talking to anybody to help allow themselves to get comfortable and when the right one comes along it'll be easier. So should I continue to just casually making conversations with strangers and wait until I'm actually comfortable asking for a number or next time should I just go for it and not even think about it. I still cannot find myself to do the 5 second rule where I just walk up to someone to talk, I don't feel like I'm prepared for that type of conversations yet. I just wanna know if my thought process is helping or hurting me?

I almost think of all my encounters as opportunities for the future since next time I see her again I can continue to talk to her and i'll have a better chance of getting a number than just asking the first time.