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I feel so social awkward lately

So there is this girl who comes in to the grocery store like everyother day at lest and she is very cute in sort of a dorky way, which is something that I think is adorable beyond belief, but she never has come over to the coffee shop, untill like last week, and it as cute cause she just had this wonderful personality that seemed to just shine, but I am like way to shy to flirt or anything with her. So then there was another day I was working and she came over again and I had the type of milk she likes memorized (most of my customers are regulars, so I memories drinks alot) and she thought that was kind of impressive and stuff. I am like man I wish I wasnt so shy.

Yesterday I was with my mom at World Market, and this mystery girl happens to work there and she totally reconized me and everything and came up to me and was like that drink was amazing and I sort of just froze up lol. It's weird it's like life is maybe saying well your 3 years of being alone all the time are finally up. But you need to make a move.

I get self concious though I am like what would I say, oh I live at home, dont have a car, and have gender idenetity issues, nice to meet you? Or do I wait till I settle those things .

I have just been out of the loop for a while, and even back hen I had other relationships it was always the girl making the moves. So when it comes to befriending the random people on the street into friends I am a bit lost