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Never. Not unless you plan leaving your job for a better advancement.
It is an absolutely horrible, stupid, downright idiotic idea to date the person who is in charge of your income and can severely effect your work environment. There are movies about this type of thing going all the way wrong and becoming a situation of financial and emotional abuse.
Not only that, but your coworkers will never give you credit where it's due because you're screwing the boss.1THIS IS NOT RELEVANT ANYMORE