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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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Therefore, if you are a good/down to earth (drug/alcohol free) woman with a sweet caring attitude, you will likely not meet a good man until ....never, because as opposed to girls who come to their senses in their late 20s, guys will always dig the hot mess (so many men cheat or leave the old used up hag of a wife for a younger model) because men value youth & beauty over anything else.