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Comments:
I would absolutely not ask her to pay for anything at this point. It'll come across as immature at best, and game-playing at worst. Wait for her to offer again, and when she does, accept it instead of turning her down.
Nice Minnie skirt*
Substitute Indian for blonde or short or thin and you get the picture.
a) will be my main issue to tackle with him. Yes he has female friends. But will he put me first?
That's like saying "a woman who is willing to risk the wrath of her date by showing up with hairy legs sounds like a woman who is confident and secure in herself"... c'mon now . I don't think anyone should pay for someone else (OR shave their legs) if they don't want to, but trying to extrapolate personal choices/preferences into personality generalizations is pretty pointless. Lots of doormats go Dutch and lots of men with strong boundaries pay for their dates/partner because they want to. In fact, the very definition of boundaries is that you get to choose them.
She stayed an hour later at work yesterday just talking to co-workers.