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You lose either way if you do. If he's not interested in you, then you'd make things awkward between you at work. Since he knows you have a crush on your married boss, his funny look may have been wondering whether you might have a crush on him as well, if that's why you are so close with him, or if it's really just friendly behavior that you're engaging in with him.
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So you really need to understand this and view this from a different perspective, she didn't sleep with these men and be with these men because she thought how great it is to have sex and play the field...she did this because she wanted someone to settle down with her for who she was and she didn't want them to run away so she gave them everything she had. She didn't think about the next guy or the future like guys do, we look at the whole picture and build our self-confidence of how many women we've been with, or we could be with, or who we can sleep with...whether she's hot and desirable or difficult, stuff like that is what makes us feel "manly".