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  • Why is it awful? You don't work together anymore if I read it right. You are a grown adult. He is a grown adult. There is nothing here but a normal relationship - albeit one that is a bit unusual in that he USED TO BE your supervisor. Would you refuse to consider going out with a person you USED to work with? You are making way too much out of what your boss used to do for a living, and too little about whether or not you actually like him. Bluntly, you are making a mountain out of a molehill. If you like him, go out with him. Certainly you won't lack for things in common to talk about.

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