Not to hijack this or anything, but what I think is interesting about my situation is that, when it comes down to dating co-workers, I always seemed to know better at first. In each of the four or five times I've been through this I didn't ask the woman out, she asked me out, usually a few times. Then I guess I was flattered, or whatever, because I gave in every time. I'm usually a pretty smart guy. Not always.
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