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Let's say it works out for a while, you have a fun time no problems with your boss- then things start to peter out and you call it quits. Unless one of you quits things will always be awkward or worse. And if she hates you afterward- you better be prepared to quit.
It's always tempting though. If someone can figure a way to solve the "should I date" a co-worker problem... let everyone know.
Please.
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"Remember, it takes two to lie. One to lie and one to listen." -Homer
Unless you are the freakin Highlander, what is the point in learning how to fight with a sword?
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