posted and copyrighted January 31, 2005

Dear Nina and Rita,

I am currently getting very close with my superior but I know he has a girlfriend and is maintaining a long distance relationship with her for about four years now. The problem is he always flirts with me through messages and asks me out all the time and always insists on paying when we go out. Although he has never made any advances on me, he has always been very suggestive in his messages to me. Sometimes he treats me like a friend and sometimes he flirts with me shamelessly but every time I ask about his girlfriend he will conveniently change the topic unless I insist he answers my questions, which I rarely do. I don’t know what to make of this. I am stuck in between treating him like a close friend or something more than that. I feel bad about flirting with him, although we both enjoy it, but I do not want to hurt his girlfriend in any way. I am 20 years old. Please tell me what to do and whether I am doing something wrong.

Signed,
Almost The Other Woman

Dear Almost The Other Woman,

If you are a 20-year-old who likes to play with power, flirting with your boss is gonna be like heroin for you. It’s almost as thrilling and addictive as flirting with your professor, or flirting with the 42nd president of the United States. Flirting is neither right nor wrong. Flirting makes us feel good about ourselves, and everyone needs a little attention sometimes, especially your superior, who gets laid once a month because his girlfriend lives halfway across the country.

Deep inside, everyone has a flirt-ometer, which gauges whether they feel good or bad about a flirtatious encounter. Your flirt-ometer readout is a blurry mixture of good and bad feelings. The good feelings are the result of feeling sexy, desirable, and clever. And what about the bad feelings? A few possibilities. Perhaps you are putting yourself in his girlfriend’s shoes, and don’t like to imagine your boyfriend flirting with another woman. Or, maybe you feel uncomfortable about the power dynamic with your boss. If you suspect that you’d lose your job if you don’t flirt with him, then you’ve got a nice sexual harassment case on your hands. Another possible reason for your discomfort is that you are repressing your desire to sleep with your boss because you can’t bear to think of yourself as the kind of woman who would lead a man to cheat on his girlfriend. Or, maybe you feel nervous about the risk of ruining your work environment if things go sour.

To figure out your feelings, you need to ask yourself what you want from your boss. You don’t need to wait until he makes a pass at you. It’s fine to say, "I’ve wondered whether you are looking to be friends or more than friends. I’ve done some thinking about this myself, and I decided that I want to be friends." He’ll be so impressed with your leadership and initiative that he’ll give you a promotion and a raise.

If you decide to stick with the status quo, your flirtatious lunches will continue to satisfy your mutual needs for playful stimulation until one of you loses interest or changes jobs. If you decide that you want to have an affair, your boss may rebuff you at first, but don’t worry: one night he will get drunk and call you. If he really wanted to be "just friends," he wouldn’t send you suggestive emails, and he wouldn’t evade your questions about his girlfriend. After all, "friends" can have candid discussions about their relationships.

You’re only twenty, and this means that when the affair gets messy, and it will, you can write it off as a youthful mistake. Sometimes we have to do stupid, dangerous things in order to figure out who we are. Sometimes we have to do foolish things in order to learn a lesson or two about life. However, before you seduce him, you need to weigh at least two possible consequences.

First, you claim to be concerned about hurting his girlfriend. Unless they have an open relationship, there’s no way you can have an affair without hurting his girlfriend. So you need to figure out how you feel about being that kind of person. It’s not equivalent to invading a sovereign nation and killing thousands of innocent civilians, but it’s definitely more hurtful than harmless flirting.

Second, you need to weigh how important this job is to you. Regardless of what happens between him and his girlfriend, an interoffice affair can have consequences for your work environment. People in your office will gossip, and you may find yourself in an awkward situation if the affair ends badly. Some youthful mistakes have a way of ruining your professional reputation. On the other hand, if you play your cards right, you can use your boss as a stepping stone to success and power. Nina never dates her coworkers, except that one guy. Rita always dates her coworkers and that’s why she loves the sex industry.

All our love and more,
Nina and Rita