PSA: Beware the Allure of the Sexy Boss

You may think that hot middle-manager is attainable -- and maybe she is -- but you've got to think big picture when it comes to workplace relationships.

Have you seen that episode of The Office where Jan and Michael Scott have that dinner party? There’s something that makes me really uneasy about that. The problem with sitcoms without laugh tracks is that you never know whether to laugh or cringe.  For those who haven’t seen it, here’s a brief background. (I’d warn you about spoilers ahead, but if you haven’t already watched The Office by now, it’s unlikely that you ever will.)

Michael Scott is the regional manager of the Dunder Mifflin branch in Scranton (classic middle management) and Jan Levitt is his cold, no-nonsense superior, completely unaffected by his incessant goofiness.  We first meet Jan during the pilot episode, where she awkwardly overhears some lewd banter about her between Michael and his chum. Anyway, long story short, the seasons proceed with Jan continually meeting Michael’s buffoonery with icy disapproval and detached professionalism. Until one night, after Michael unwittingly negotiates a lucrative business deal over an Awesome Blossom, she throws herself at him, beginning a scandalous tryst that flies in the face of corporate policy.

Jan—a clearly troubled woman who underwent a divorce (because her husband didn’t share her desire to have children) and currently harbors a drinking problem and self-esteem issues (see: impetuous boob job)—becomes even more troubled during her romantic entanglement with Michael. Like some kind of gender-swapped Delilah, he seems to sap away her dignity and strength. As soon as she enters into a relationship with him, the power structure is inverted. She loses her job (because of the relationship) and descends into a manic, yet tragically deficient parody of domesticity. During the dinner party, she is humiliated as signs of her sexual kinks, her ambiguous relationship with her former assistant, her failing candle business and her overall inability to keep it together outside of a corporate environment are put on display before her former underlings. The night ends when the Scranton police join the party on a domestic disturbance call to find Jan, dripping in denial and Michael awash in obliviousness.

So it's just a TV show

I know it’s wrong to psychoanalyze a supposedly lighthearted comedy. But I can’t help it. The most disturbing assessment I’ve heard about The Office was something along the lines of “It’s funny because it’s true. It’s just like at my workplace!” With that in mind, there’s something almost sadistic going on here. It’s almost as if the creators of The Office are appealing to this primal urge inside men to sexually conquer their overbearing female bosses. We’re asked to delight in Jan’s downfall which, to me, feels a little bit unhealthy.

This whole Michael-Jan relationship originally inspired me to write a how-to article entitled “How to Woo Your Female Superior” as a field guide on how to court your boss in a classy manner. But the deeper I delved into this subject, the more apparent it became that the first and last step of this tutorial should be “don’t.” And if you need more convincing than the cautionary tale aired on TBS, then read on.

Full disclosure: I don’t work in an office and I don’t have a boss. I’m aware of the fact that this may limit my experience on this issue. So I turned to some experts to find out:

  1. Why men sometimes find their female bosses so attractive
  2. Why it might be a bad idea to pursue a relationship with them
  3. What’s the best way to go about doing so, if you simply must.

I talked to experts on relationships, careers, sexual harassment and even psychology and here’s what I discovered:

Corporate Sex Appeal

The sexual conquest of the authoritative woman has long been the subject of male fantasy. From The Graduate to “Hot for Teacher,” there’s something undeniably macho about scoring on someone who is out of your league in almost every way. But what’s up with that?

“Hello, mommy issues!”

That’s the initial assessment that I got from Brooke Miller, a relationship therapist who you may know from her regular Soapbox Therapy columns here at Primer. Brooke’s not a Freudian psychologist, but she still had a thing or two to say about the Oedipal complex, which clearly factors into this whole mess.

She explains that as a child, your mother is literally your first love. Of course, this doesn’t mean that little boys want to have sex with their mothers (they are little boys—they don’t want to have sex with anyone). It just means that they want their mothers to love them best. The classical allusion comes in as the young boy competes with his father for the love and attention of his mother. Losing this battle (as most children inevitably do) leads to resentment towards the father and bittersweet ambiguity towards the mother.

office relationships by the numbers

So, what does this have to do with sexy bosses? It turns out that until you reach a certain level of maturity, the distinction between emotional love and sexual love is poor or nonexistent. So if you don’t get that love and fulfillment that you sought as a child, it just might follow you into adulthood—and it just might get conflated with sexual desire for motherly figures.  (My two cents: the need for emotional/sexual fulfillment likely further gets muddled given the confusion and trauma that typically unfolds during those first, often ill-fated teenaged sexual encounters—but I’m no psychologist.)

This becomes more complicated—and potentially more scintillating—when you introduce a love/hate element. Not to bring another sitcom into the mix, but Buster’s relationship with his mother in Arrested Development is an excellent (though over-the-top) illustration of confused sexual desire and child-like rebellion against a parent. Inflect this into a relationship with your boss, and it gets a little bit simpler—you hate your boss because of her overbearing authority, but on the other hand, you still long for her approval (and perhaps affection).

That may not be the case for every guy who’s got the hots for that stone cold fox from corporate. But the takeaway is this: your attraction to a female superior may have more to do with what she represents than who she is. You’re harboring desire for a woman who holds a certain meaning. That can be traced to mommy issues, rejection by the head cheerleader in high school or a salacious lust for the taboo.

There are other factors, too, of course. Maybe you just dig a brainy lady with a confident step and a powerful pinstripe pencil skirt. If so, pursuing a woman higher up on the chain of authority is a safe way to court a woman who may be smarter and more successful than you without feeling emasculated. Then there’s the issue of environment: stress and suspense, narrowly averted crises, constant external threats and the other high octane ups and downs of the corporate environment can synthesize feelings of solidarity. In fact, the rapture following Michael’s clutch win at Chili’s was what spurred Jan’s first sexual advance (not real life, I know, but close enough). That was pointed out by Dr. Lunell Haught, a certified management consultant, who advised that attraction that blooms in the adrenaline-filled workplace might not be so magnetic in the cold light of day.

It’s also important to look at the situation from your boss’s perspective. Why is she attracted to you? Is it because of who you are, or what a man in your position means to her? Is she working out mommy/son issues in reverse (I think that’s called a Jocasta complex)?  Or is she simply a busy working woman who never sees a man outside the office and she’s just using you to scratch that itch?

Like most sexual fantasies, the allure of the hot boss can easily be dissipated upon consummation. This is a two-way street. For example, there’s the classic male fantasy where he coaxes a conservative, straight-laced woman to let her hair down and allow him to satisfy her repressed primal urges. Or the converse, where a girl wrangles an unfettered bad boy and reaches past his tough outer shell to stroke his heart of gold. The problem with fantasies such as these as driving forces for either relationships or  flings is that once you peek behind the curtain, the magic and mystery disappears.  Then, shame or regret quickly fill the void.

The takeaway is this: your attraction to your boss and her attraction to you are likely built not upon compatibility, but on deep-seated issues or wild fantasies. You don’t have to watch much TV or read a lot of Sophocles to know that that’s a recipe for disaster.

Abandon Hope All Ye Who Enter Here

“But,” you might say, “I know the score. I’m just looking for some salty copier room action. I don’t care if she likes me or not—I ain’t gonna marry her.”

Okay, fair enough. But if you think you can get in and get out with your career, your dignity and your friendships intact, guess again. The office relationship is already littered with occupational landmines, but when you dally with the higher-ups, it’s ten times worse.

An office romance puts all of the following at risk:

  • Your job. If the corporate policy doesn’t get you, the fallout from the inevitable end of the fling will. If you break it off, you may face retribution. Or, if/when the cat gets out of the bag about even a one-time hookup, she may overcompensate to avoid accusations of nepotism and nerf your rise in the ranks. Also, as the relationship fizzles or ends in misadventure, the awkwardness could haunt unbearably until one of you quits. And since we know that she has a better job than you, I bet it’ll be you that folds.
  • Your camaraderie. That is with your fellow coworkers. Sure, you may get a high five or two when you first break the news, but as the novelty wears off, you’ll begin looking like an outsider. You’ll be resented for perceived preferential treatment or promotions, even if you truly deserve them. And your friends may feel hesitant to speak freely in your midst, for fear that their venting might make it into your next pillow talk session. Nothing brings coworkers closer together than griping about The Man (even if he is a hot, sexy female man) and by shtupping her regularly, you’re excluding yourself from that conversation.
  • Your heart. Not trying to get mushy here, but in virtually every sustained affair and even in some fleeting rendezvous, feelings develop. Even with a “pre-coital agreement” (either spoken or unspoken), breaking it off could be rough for either one of you. And remember what I said about issues being a shaky foundation for a relationship? Yeah, it’s not good news.

That’s by no means an exhaustive list, but you get the idea. Whenever you launch a sexual crusade of your female superior, the stakes are all or nothing. And the cards are heavily stacked against you.

dating your boss

If You Just Can’t Help Yourself…

As I write this, I realize that the type of guy who might fancy a lady boss in the first place is exactly the kind of guy who’s going to get even more fired up upon learning that it’s an extremely high risk venture. So, like the sex ed teacher who reluctantly teaches his students how to put on a rubber, I’ve got some advice for you.

The number one thing to remember: “No means no.” Persistence is cute when Ben Stiller does it on the big screen, but in the office it’s not just unseemly, it’s actionable. That’s right, I’m talking about sexual harassment. For this tricky subject, I consulted Asher Adelman of eBossWatch. His company keeps an eye on workplace skeeziness with their listing of America’s Worst Bosses and their National Sexual Harassment Registry. His advice:

Having a fling with your boss is risky business. First of all, unless your boss is giving you clear messages that she’s interested in you romantically, any flirting can potentially be interpreted as “unwanted advances” and even sexual harassment, which will probably spell the end of your job. The difference between flirting and “unwanted advances” in the workplace is that only your first attempt will be considered flirting. Unless the woman reciprocates and flirts back, your subsequent approaches could be considered “unwanted advances.” On the job, you should definitely take “no” for an answer.

Even worse, sexual harassment could lead to a lawsuit. And the thing about lawsuits is that they don’t even have to have merit to become a career-ending PR nightmare. Let’s say your boss gets jumpy about getting found out and throws you under the bus. It’s your word against hers, and it’s going to be a rough day in court.

Aside from that, the only other pointer I can give you is to use what you know to your advantage. Consider why she might like you and play to that. Consider the situations that might bring you closer together. At any rate, you aren’t going to be able to woo her like you would a girl at the bar. Adapt your game to the workplace. Depending on your work ethic, you might run for the door the next time they ask for volunteers to pull an all-nighter on a project that’s nail-bitingly close to the deadline. But don’t—pulling off a miracle is one of the best corporate aphrodisiacs. Stay professional when the situation calls for it and be subtle and classy when you have the opportunity. Patience is the game here, and it’ll work in your favor—you see this woman every weekday, 52 weeks a year, so take your time. At best, it’ll build tension. But you’ll also have time to assess whether you’re reading the signs correctly and, if not, your restraint can possibly avert a disaster.


I set out researching this article trying to figure out the right way and the wrong way to court a female superior. Much of the advice I received seemed to indicate that there are a million wrong ways to do it, a handful of risky, but possibly okay ways to do it and no perfect avenue for romancing your boss. There’s lots to lose when it comes to pursuing a female higher up—but then again, there are high stakes for just about every relationship. Just make sure you know the score before you place your bets.  I’ll leave you with a last bit of wisdom from Brooke Miller:

There is nothing necessarily wrong with it—it depends on the situation. Everyone has baggage, the best relationships are when everyone’s baggage matches up and works well together. But, be mindful of your career—there is no such thing as a flawless, perfect, drama free relationship. Don’t be delusional and think that your situation is different. Sorry about your mommy issues, I know you want to feel like a big boy…but you’re not an exception to the rule.

Header photo credit: ©
AC Burke

AC currently lives in New Jersey.