Dealing with WAW Part 2

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pilot I say do it only if you don't care what her response is, meaning that if she says no then you are good either way. You have come a long way, don't loose your ground...maybe suggest to her at the pool if she would like a drink, then as the day goes by casually say "man im hungry, how about you?" then if you make it that far order drinks at dinner, that way she wont feel like you asked her out on a date, it will look like it just happened.