Bedding the Boss

The Letterman scandal raises questions about the wisdom of sleeping with your supervisor. Tracy Quan on what women want—and how the rules of the game have changed.

John Paul Filo, CBS / Landov

What kind of woman sleeps with her boss? In the ’90s, she was cast as a victim, in the ’60s as a predator.

David Letterman's televised account of a blackmailing attempt concerning his sex life has raised inevitable questions about whether he abused his power in the workplace.

Letterman is, however, atypical. Most women don’t work for the king of late night comedy, and most sex-with-the-boss (we hope) is unlikely to attract the attention of Gawker or TMZ.

Common sense tells us that lots of women are attracted to father figures and mentors. Banning such a relationship doesn't just put the brakes on male desire. It’s also an attempt to suppress some healthy female impulses.

Wherever it may happen—whether in media, banking, or a more down-to-earth industry—a man having sex with younger female colleagues is characterized as a lecher or a domineering ogre.

Once upon a pre-feminist time, it was more common to vilify the woman. In the ’60s, she was an ambitious vamp out to destroy her boss's marriage, and the early modern workplace was seen as a hunting ground for capturing a husband—anybody’s husband. As middle-class women became more careerist, this phantom vamp used her carnal savvy to “sleep her way to the top.”

Whether you're the masculine monster in this story or the feminine schemer, you're a dehumanized cartoon.

Still, in the pantheon of stereotypes, culprits are more colorful. Feminist tropes about sexual harassment can make working women seem like ciphers. If you think back to the stories told about Clarence Thomas, he had the best lines and a far more memorable personality than his offended victim.

After making a transition from prostitution to publishing, I find the idea of bedding a boss shocking. I would be horrified if someone I work for came on to me today, but I wasn’t perturbed when it happened in the sex industry. My only experience with sleeping with the boss occurred in my teens. A madam asked me to be part of a three-way with her boyfriend.

Paul Shaffer on being Letterman’s comic foilLloyd Grove: Is This Dave’s Blackmailer?It was more like found money than coercion, but it would have been awkward to say no. Since she was my only professional contact in the New York industry, I was dependent on her for business and never considered refusing. We had our session before, not after, dinner - a nice touch on her part—and she was an eminently civilized sex partner. A few days later, I compared notes with a male escort who, I was amused to learn—resented having sex with our boss. I really didn’t mind.

Mainstream feminists may regard Stephanie Birkitt, believed to be one of Letterman’s office affairs, and other women in her situation as victims of a power imbalance. This is the official ideology in many a workplace where sex between senior and junior staff is verboten. But common sense tells us that lots of women are attracted to father figures and mentors. Banning such a relationship doesn't just put the brakes on male desire. It’s also an attempt to suppress some healthy female impulses.

It may, in fact, be harder to police female behavior in the workplace, harder to tell women to keep their hands off a man and easier to tell men what they may or may not do—because women and men express attraction and desire in different ways.

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If sex between a male boss and his female staff is purely the result of masculine appetite, it’s more easily prevented. The average male likes to know how the system works, what’s available and what’s not. Women are less obvious. We like to break rules, even when we don’t own up to it. We also don’t love being told whom we should be attracted to.

A dominant theme running through pop feminism, affecting so many areas of our culture, is that a woman should mate with an equal—a man who is more like a brother than a father. For many women, peer love sounds okay in theory but spells bed death in practice.

The architects of contemporary regulations do not have women’s sexual happiness in mind when they transform the father figure or his female protégé into forbidden fruit. What they have in mind is avoiding lawsuits when things go wrong—which they sometimes do. But rules which prohibit intimacy between older men and younger women will always be broken because the camaraderie of a guy who does the same job you do for the same pay is not every woman’s erotic cuppa.

Helen Gurley Brown, who invented Cosmopolitan magazine, had some interesting advice for the working women of her era: since you sleep with everyone else, why exclude the boss? From that perspective, lying down with your supervisor doesn’t seem like a bad idea, but things have changed quite a bit since the Cosmo founder’s heyday. White-collar jobs were more plentiful. Many of the women she spoke to through her books and columns had jobs that don’t exist anymore. They operated under different rules.

Helen blithely told young women that, if things got sticky with the office lech, the graceful thing to do was scoot—find another job. Her advice sounds outrageous to our 21st century ears. At the time, it wasn’t so unreasonable. If you worked in a large urban center as a receptionist or a secretary and you slept with your boss (or turned him down), things might get uncomfortable—but there was a good chance you would find a similar job elsewhere. The process of vetting a possible employee was less rigorous, and a woman who followed this advice could feel self-sufficient rather than aggrieved.

White-collar female aspirations have changed. There’s more at stake if a junior banker with an MBA sleeps with her boss: before even getting the gig, she begins to invest heavily in her career. If sleeping with a managing director turns out to be a mistake, she won’t just be walking away from a job. The more women invest in their careers, the fewer romantic chances they can afford to take. You need not be a right-wing troglodyte to see this as a regrettable consequence of progress.

On the other hand, you don’t have to be a feminist to find sex with the boss problematic. In a recession, with New York unemployment in double digits, sex with the boss could be murky. A woman might feel genuinely threatened by a flirtatious senior figure. Now that so many of her friends are unemployed, she wonders about the consequences of turning him down. Even if she actively wants him, how easy is it to enforce safe sex? Does she feel pressured to have sex without a condom, engage in things she doesn’t like, or fake an orgasm to bolster the boss’s ego? If you get into bed and find that you’re sexually incompatible with your boss, an extra layer of diplomacy is called for.

In other words, sex with the boss might not live up to a woman’s fantasies—and it may be more tactful, more self-preserving, to enjoy a controlled flirtation.

Sex with the boss can also be seen as the kissing cousin of date rape. One woman’s ill-advised adventure not worth repeating is another woman’s terrible violation. The same truth applies to sex with a superior. As the relationship continues, a woman may find that sleeping with her boss robs him of authority and makes him rather vulnerable—not only to subtle forms of blackmail, but to outright requests for special treatment or a well-deserved promotion with extras. Other women in the same situation feel compromised and embarrassed.

If you’re a woman who marries her boss, you’re less likely to be seen—by yourself or by others—as a victim of the power imbalance, but marriage is not everybody’s goal. Even if you just want to be a friend—um, employee with benefits—some feminists are determined to see every favor you receive as a form of injustice. Is this really progress?

Tracy Quan's latest novel is Diary of a Jetsetting Call Girl, set in Provence and praised in The Nation as a "deft account of occupational rigors and anxieties before the crash." Tracy's debut, Diary of a Manhattan Call Girl, and the sequel, Diary of a Married Call Girl, are international bestsellers. A regular columnist for The Guardian, she has written for many publications including Cosmopolitan, The Financial Times, and The New York Times.