I definitely will not let it turn into a sense of entitlement. Its more of a feeling like "Ok I've failed enough times that I can see some of the places that I have messed up before. And besides, statistically speaking I should have some form of success soon." I think the events in the organic food store show that its not impossible for me to interact with women on a more than friendly level.
Sense you bringing up martial arts in relation to women there is something that I learned that may help you. You say that you are afraid to let people see your weakness. A smart worrier knows that by intentionally leaving one weakens open , he can provoke the enemy to attack it. Knowing how the enemy will attack the worrier can then counter and thus achieve victory. This works with women to. A man can some times show a small vulnerability to a women to make her feel closer to him. A man with no vulnerabilities is perfect, an nobody likes a perfect person, they just make others jealous. Its the character flaws that make people interesting. We don't love Bat Man because he is perfect, we love him because he is damaged but still keeps going no mater what.