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A boss is an authority symbol and generally pinpoints the subject of the dream as being related to a waking life work or career issue. The relationship with your boss in the dream may reflect literal aspects of your working relationship or may symbolize your feelings about your boss, job or company. An inappropriate romantic relationship with your boss in your dream may reflect your attraction to qualities that your boss has or may reveal a more literal romantic interest. If an old boss appears in your dreams, it may represent your sense that the current dynamic with a superior at work is similar, or it may reflect your preference for that former relationship.