The Only Prescription...

Sometimes, during my day to day activities, I’m prone to develop crushes on particular women who I’ll encounter on a fairly frequent basis. A few years back, there was a nice and attractive woman who worked as a cashier at my regular grocery store. She will forever be known as the “Sweet Sweet Checker Girl.” She was so pretty and friendly and fun. She made easy conversation and seemed very genuine. After months of her ringing up my groceries and seeing my bad habits and such, I managed to learn a little about her as well. I learned that I really liked her. Eventually, I managed the nerve to ask her out, while she scanned some treats I was buying to bring in to work the next day, for which I asked her advice. I made this move after asking a few close friends what they thought I should do and how I should go about asking her out. I never feel good about asking someone out. I feel like I’m committing some sort of crime. This feeling clearly shows that I have issues, but that can be addressed some other time. At any rate, most of the offerings I get from my male friends essentially amounts to things Trent would say in the movie “Swingers.” There is always a specific strategy and game plan and a message to let me know how “money” I am no matter the result. On the other hand, without fail, the message from my female friends is to “just be yourself.”
On the one hand, I sometimes sigh in the face of the message I get about me being “so money,” but I do find the game plan part of the hints to be helpful. However, the “just be yourself” advice simply confuses me. If I am to “be myself,” then clearly I would never have a shot. Just being myself has led me nowhere in my twenty some odd years of being someone who wouldn’t mind having a relationship. Also, for anyone that knows me – or has known me – when have I not been myself? The answer could be the few times I’ve duped some woman to hang out with me. Once the “being myself” part comes around, those relationships seem to deteriorate in some strange friendly way. They always peter out quietly. I am clearly better at being a good mate (as in friend, buddy, etc.), than I am at being an actual mate. Case in point, the Sweet Sweet Checker Girl turned me down when I asked her out. She had just found herself engaged the weekend prior (I have incredible timing). Oddly enough though, she thought so much of me that she continuously updated me on the wedding plans and eventually she showed me pictures of her wedding. Before she finally quit her job at the grocery store, she gave me a hug and said that she would miss our conversations.
Well, I’m at it again. I have developed another similar relationship. I am hoping to ask my latest hopeful flame out this week to a show ("flame out"...interesting). I made an effort to flirt and get to know her on a personal level recently. I found out that we may have similar music tastes and that she loves going to see it live. This gives me a game plan and allows me to “be myself” in an area that I am most comfortable in. Additionally, she works tangentially in the medical field, which could also help. During my very involved medical history I have found that I exude some sort of strange confidence in hospitals, clinics and doctors offices. Will this mean I am “so money”? It remains to be seen, but it always feels unlikely.