I need social help with women!!!?

I seem to have a problem...a social problem. All of my life I have somewhat had this problem but over the years it has become more and more noticeable to me. Physically I would say I am around an 8, not being y this is just the reaction I usually get from girls, I often get "the look" when I am out and about doing errands and what not. But its my personality, I really don't understand.to give an example if I am at a party I often times will slip into this observation mode, I will just sit and observe other poeple, the conversations in the air. I will point out peoples errors in my head and then after a few minuets snap back to reality and realize how stupid I probably look. I am just an observant person, always studying peoples personalities trying to pinpoint why they act the way they do, i don't know i guess peoples emotions just fascinate me. Yet I am the epitome of the kind of poeple I dont like and make fun of. the socially awkward people, the people who try to hard to impress others, the tools. I am always worried about making friends and people liking me, I usually have to get to know a guy and the stuff he likes and his type of humor, once I know this about somebody I become there friend, this seems sort of fake to me, as if i am studying them so I can act the way they would want someone to act,sounds messed up I know. Also I will meet a guy who has a funny personality that my other friends like and I see this and get his personality stuck in my mind(not the guy..I ure you I am not gay) and start to try and act like he does, I don't want to do this...it makes me feel like I have no real personality.I want to develop my own unique self but I honestly am afraid people will not like who I really am under it all.back to the reason this is such a problem with me, I never seem to do good with women, not lately anyway. I guess I have just been rejected so much, cheated on or just messed with by a girl, I feel like there is something wrong with my personality, I mean there must be, why else would this always happen. What I hate most is that girls are always so interested in me when they first meet me, I don't mean to sound arrogant but I must be attractive because this ALWAYS happens to me. A girl will meet me and be interested/excited,they will tell me they think I am really cute/hot or whatever. but then it is like once they get to know me they realize I am boring?I try very hard I will admit,I know trying to hard only makes the situation worse. Usually what I will do is try and be funny, or act cool. eventually I mess up, I say a joke that is inappropriate or I will come off as an ***, but yet this is what people say girls like, the guy. But that never works for me. I cant be to nice because then I am just the nice guy and I become the friend who they don't see as a boyfriend(has happened to me a few times). Hearing this is painful, I feel like I just.. am not date-able. What gets me is that I have a plethora of "interesting-ness" about myself, I love music and listen to so many different kinds. I play guitar. I love art and draw extremely well, people are always amazed by my art.I love movies and know sooo much about directors and actors, I love literature and nature and just life in general i find it to be so beautiful. I almost feel like I am TO down to earth(if there is such a thing), social conversations are an act and I feel like I need to be acting when I talk, I know this is strange but I just think so deep into things that it ruins the whole situation. I could be on a date with a girl and I will always come to a point of not knowing what to say, then anxiety kicks in and it becomes worse, now I can't think of ANYTHING to say..then there is awkward silence and to me that is when a girl decides your not her type, when you can't think of anything to say to each other, i hate this because I feel like I have ruined it when if I just new how to come up with interesting conversation or be myself I could have a much better love life. I have been in a realtionship for a year before with a very cute girl so I am not a freak, I am social, its not like i am just a recluse. I have a lot of friends who I don't really feel socially awkward around, they all like me and like to hangout with me.I have friends who are girls, cute girls. it just seems that when it come to flirting with girls i don't know what i am doing. Or when i am alone I try so hard to generate interesting conversation, what would you typically talk to a guy/girl about who you are dating while you are alone? I know there is a lot of going on in this question but any advice, even criticism is acceptable so please, give me your feedback!