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This is very interesting actually. My advice is not needed sadly as I am not legal drinking age in the states. I don't know if I would do it though, it's like dating one of your best friends girlfriends best friends...that sounds so confusing but I hope you get what I'm going for...it may end up awkward no matter how it works out.
I would suggest getting to know her better apart from work though if that is an option.
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