There must be a fault in your system somewhere. In order to break the cycle you must figure out what's going wrong and fix it. Give us an example of what a conversation between you and a woman that your trying to pick up. Also Im getting the feeling that you feel awkward when you approch. That...
If I ask someone out than naturally I should pay, but if she asks me out than she should pay. I honestly don't believe paying for a date that you asked her on is supplcating. As long as its cheap.
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