This is the problem of most of us, we prefer to be excited with the truth but does not want to take the risk of acting. From your story I visualize men and women wondering

what if I go for the $500 and he doesn't give me, what if he is just using it for illustration ,people will see me cheap if I go for it, I will be laughed if I go for it and he deny me*

This kind of inner thought has being our barriers to why we don't take action ,they set us in a comfort zone where you are limited in life. And the only way out of it is experience the fear and take action anyway