Don't know why I feel this way when thinking about talking/or talking to a woman?

Whenever I think about approaching to a woman or I am starting to them, I start this feeling of inadequacy. This due to not know the in and out of talking to women, and not necessarily being where I want to be. I have a great career, but currently trying to pay off student loans (still live with the folks). Then try to save up to a good point to get a house eventually. I am also thinking of ways to also make passive income. It's just there is this inherent issue that I have which I don't know why, where I see a woman and tell myself she won't like me. I don't have all the qualities they want in a guy (even though a lot of the women I talk to are in the same boat of trying to figure out life. Some on the other hand seem to have everything figured out which does make me feel some type of way). I just don't know how to figure this out and conquer this feeling.
Don't know why I feel this way when thinking about talking/or talking to a woman?
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