HBB, you need to sleep with a prostitute (or at least get a blowjob) to get some confidence, and stop overanalyzing someone saying "hi". You can use that brainpower which you obviously have to get plenty of women, but first you need to get un-frustrated by experiencing sex. She would have been a girlfriend or friend if you just had sex 1 time previously so you weren't being a frustrated weirdo. Also you need to stop telling yourself something's wrong with you. It's far better to be massively overconfident and ignore any flaws than to be underconfident to the point of submission to any woman like this...