Cernan,
Listen, I'm 250lbs and have been like that for too long over the last several years. It's unhealthy and I'm struggling with a diet regime. But it hasn't stopped me from finding love with a woman despite how much I hated being overweight.
In your case i see that it's a problem with self-confidence and the terrible fear of rejection- at work, in a bar, at a party. How much of that is a function of the mores of the society we live in? The 'gotta be thin' look all over the media makes it seem imperative and it's not at all.
Maybe you're seeing women like that too? maybe you're seeing only the "lush" women and wanting to "score" with them as "chicks" when what you might be doing is talking straight-up to any woman, lush or not, as tho' you were there for a conversation and not looking for a quick sexual snack. What's wrong with just being yourself when you meet a woman or start a conversation with her? Danielle is so right... it doesn't work to approach every meeting with a woman by seeing her as a potential 'score'... how about just a frequent, non-threatening, "Hi!" in the office for a while and then moving on to appreciation of her plant-life or the photos on her desk - staying away from overtly personal matters which are not appropriate in the office anyway? What about asking about what you may have heard about her - is she a dancer? An outdoorsy type? A movie-lover? A shoe fanatic like Imelda Marcos?
Here's the rub and it bears saying over and over again - there will be rejections along the way... that's nothing to fear... it just is that way... so she is a rude woman and turns her back or sidles away from you... happens to all of us one time or more. So, you just met a woman who is lacking in social skills, that's all. You don't have a sign on your forehead saying I'm looking to get laid tonight, right? Keep it neutral in chat until the smiles are natural and she's asking you questions.
You don't have a problem starting a chat with some guys in the bar, do you? Do it the same way with a woman. You're talking to a human - people are receptive or grumpy or inarticulate or so verbally effusive that you won't want to stay there too long... it's all kinds... there's no formula, Cernan.
If you really want to go for 'classes' on being social go to a dance class, join a drama group, do what you're doing in here - say what is in your heart and damn the torpedoes.
Hey, I like you because you're honest. A lot of other people will appreciate you just for that quality you already have...use that skill and look for honesty coming back at you.