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eharmony Relationship Advice» Dating» Dating your boss – the pros and cons. Dating your boss – the pros and cons. with other work colleagues – even if you think that the other people you work with are your friends if your start dating the boss you could find yourself the subject of gossip. Your co-workers may be ok at the. On the first day, my boss, Justin (not his real name), came up to me to say hi while I was setting up my voicemail. As we worked on the second bottle, we started talking about what dating is. Aug 25, · My boss really wants me to date one of her sons. She says she really likes me and we would be cute together. Problem is her son is really hot and I'm more of the girl next sowereadthisbook.com: Resolved.
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