Good question. I can understand your discouragement. I guess that you may need to refine your social skills a bit. For example, if you feel awkward, it could be you come off that way. Sometimes we have to "fake it till we make it" by acting more confident than we feel. It's also possible you need a man make-over. You'd be surprised how much a good haircut, cool clothing, and good shoes will make you feel.
Whatever you do, don't ever give up asking women out. There is someone out there for you. If you have to slow it down for a time while you learn how to be more comfortable in your own skin, then so be it.
You might want to take a karate class, or something along those lines, to help give you the boost of confidence you need. Whatever you do, stand with your shoulders back and go tackle this thing. You can do it!