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I know my problem is that I care too much about what girls think and I have low self esteem.
Indeed I agree this is your problem, good that you at least realize this.
Thats awesome that you dont have much of a problem with AA. If you see yourself as boring then you clearly seem to think you have a boring life. Is your life that boring??
To help you talk about yourself, sit down with pen and paper and write down some cool stories/memories that you would tell your close friends (read up on DHV storesi if you dont know what they are, but mainly they shold be stories from your life that you ENJOY telling which convey your personality and your past).
Then the other side of the coin is to be genuinely interested in what SHE has to say, if you develop this curious mindset you will be naturally inquisitive and threads of conversation will spawn naturally.
If you see yourself as a boring guy, you will be boring and have no chance mate. Dig deep and find the you that's interesting, confident, adventurous, flirty, cocky, smooth, charming, sexual. (you have experienced all of these at some point in your life, try and remember those times and recall how it feels).
It really is all in your head.