Hard time making a connection and trying to getting 'the lady'?

Well I have a hard time making conversation in general with people. I always feel like a "fish out of water," especially with women. The reason why I say that is I have a very hard time trying to converse with women, and making a connection. Even though in my heart I really want to get the specific girl I am attracted to. Like for example my friends are always pushing me to go speak to different girls (I know why they're doing it, because I need to get better). The same time I just don't know how to really speak to women and create a connection. I have several dates, but nothing has really made it past three/four dates (except for 1 that we were dating for about 3 months). I tend to be the homebody, and like to really keep to myself (aka loner), I rather stay home and go watch a movie. I have gone to bars and so forth with a few friends. Despite being a self-proclaimed, yet other folks say that I am very outgoing. Not to mention that I am short 5'9'' and about 201lbs, so I tend to be short and chubby, not to mention not sure of what to do due to my past and current failures. It is very difficult, because despite my trying I guess the girls see that (since I have been told a few times that I was "trying to hard", with a particular girl I was talking too). In a way I guess I am tired of being single and at 31 years old I am not getting any younger and want to start a family when I get out of grad school. So I am looking for advice, because I want to be able to outshine the other guys. I am tired of seeing the other guys taking the girls I am interested in (which has happened to me super recently), on top of having to be around two girls that I am attracted to and been rejected by (well actually by one, but the other is her best friend and I can't ask out the friend now, since they are best friends. On top of that I am not even sure I she is even attracted to me). I am always a nervous wreck, because like I said I am tired of being single.
Hard time making a connection and trying to getting 'the lady'?
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