Love, Inc.

Q:
My boss is a very attractive middle-age divorcee whom I’ve had a crush on ever since I stepped into her office, and I think she’s attracted to me, too. We spend hours talking and she flirts with me all the time. Should I make a move and ask her out?

A:
Have you ever heard the expression “Don’t shit where you eat?” As crude as that maxim is, it pretty much describes what getting involved with a boss entails. Many companies have policies against interoffice romance – particularly those involving a power differential between employees, because these relationships may become exploitative. Moreover, if the affair develops into a relationship, do you really want your girlfriend to be your boss? Just make sure your intentions are genuine. Power can be intoxicating, and your attraction for this woman may be based on her position rather than true interest. If this is just a crush, it’s not worth risking your livelihood for. However, if you are truly interested in your boss for more than a roll in the hay, you may decide that our career and your job are worth risking. So figure out if she’s crushing back by making a mild sexual innuendo to gauge her response. (Raised eyebrow? Bad. Half smile? Proceed.) Men often misinterpret female friendliness as a sign of sexual interest, and the last thing you want to do is create and awkward situation with someone who’s responsible for your paycheck. Good luck!

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Victoria Zdrok's combination of beauty and intelligence has earned her the label as "sexpert" in many media outlets. She writes a monthly column on love, sex, and dating for Penthouse Magazine entitled "Ask Dr. Z," and a column on sexuality and the law for Penthouse Forum. She is a frequent contributor to several publications and has her own SIRIUS Satellite Radio specialty show, The Sex Connection, on Howard 101. You can find out more about Dr. Z at www.sexysexpert.com