Why did he seem to like the idea that I don't have much confidence?

I honestly think that he smirked because he thinks u don't have confidence in yourself when u do it's just u don't see yourself as others do and u question it so he thinks u don't have confidence.. I think you should just tell him straight up that he should go move on to someone else because guys can be very persuasive ! Believe me .. Dont think of yourself as not confident and go enjoy life ... If you do think ur not confident go change that .. That's what I did and now I got all these guys after me ... Good luck :)