Sleeping Up: Why I Had an Affair With My Female Boss

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Photo: Tim Macpherson/cultura/Corbis

In those first few weeks after moving to Chicago, when part of me already knew I was going to end up sleeping with my married boss, I tried to distract myself by walking around the city. I didn't have a car, or a license, or even an idea, really, of why I'd moved there, except for a job. So I walked across a lot of bridges and ended up in a lot of bars. Every booth was filled with another season's hopeful fans, the waitresses saying: "Don't count on it, but what're you having?"

I’d spent the past few years in New York at an office with a Jaegermeister slushy machine, a bumper pool table, and a rug that was woven to resemble the editor’s face. But in Chicago, my office was staffed by adults who had mortgages and commutes, children and failed marriages. The accounts director was dating the manager of a sports team. The sales rep, I’d heard, had lost a spouse to a mysterious accident. And my boss, she had an estranged husband and had been working there for over a decade. I guess you could say it was like starting to watch Friends in the fifth season: You don’t know the characters, but they all have backstories, and they’ve all slept together. And one of them used to have a monkey. But of course, it was more complicated than that.

We first got together one Sunday at a wildly mediocre Irish bar after five Bloody Marys. We’d been Gchatting about work, as we usually did, though it had always been hard to tell where the work stopped and the flirting began. I said I was bored. She said, "You’re welcome to come down and have a drink with me." I walked the few blocks, excited, wary. I think we both knew what was going to happen. After the fifth drink, she said that this could get us in trouble. "Yeah," I said. And that was it. We walked the two blocks back to her apartment, in silence, through the parking garage, and up to her place.

Here's how it worked: during conference calls, I'd put my hands down her shirt. We'd go back to her office, down the hall, lock the door, and put the phone on mute. What if somebody knocked? Nobody ever knocked. In the office, she wore tight skirts and tall heels and would stomp around, from office to elevator, with her head bowed monastically over her Blackberry. She was a thin woman, predaciously fit, and her heels always made a clomping sound, a Jimmy Choo herd of one. She got manicures every week, and that seemed somehow exotic. She wore suits. She was smart. Whenever I saw her blonde hair, I thought: lightning. She was my first adult, 40 to my 32.

Most nights we’d go back to her place, an apartment across the street from the office. She rented a one-bedroom, furnished, so it was decorated in that means-nothing way. It could have been a dentist’s office. Her dog was too big for the space. It whined when the bedroom door was shut, and watched us when it wasn’t. Sometimes we’d go out to dinner where we wouldn’t be seen. Sometimes she’d cook at home, and that was nice. Sometimes we’d growl under the covers and ask each other those things new lovers do, like could anybody else be quite as good at this as us?

I remember exactly when we first started saying "I love you" — in bed, after a work party maybe three weeks after this whole thing started, with her husband texting and asking where she was — but I still can't tell you whether either of us meant it. It seemed like we backed into it, like two people in a movie backing into each other, each holding a flashlight, afraid of something else in the dark. Maybe we needed to say it, to make the whole liaison worth the risk. I don't know. But we said it. Then she had to go home to the man she married. "Don't worry," she said. "We haven't had sex in two years." "Oh," I said. Well. In that case.

They'd married years before. Bought a house in a wealthy subdivision, one of those places with a vaguely Victorian name where housewives have earnest conversations about wainscotting. She sewed the curtains and hung them. She installed a toilet by herself. There was a backyard for the dog. But then came the troubles, and then they sold the house, and then he took a job in another city, and she moved into that apartment, alone. He came back to visit twice a month.

What had happened between them? What rancid thing? I didn't ask questions because I didn't want to know the answers. When you're a grown-up, and you sleep with your boss, you're checking off a fantasy. You are turning the tables of your employment. You are possessing the thing that possesses you. But what kind of man sleeps up? I'd heard of women sleeping with their bosses, and it always seemed to be about access to power. Was that what I wanted? To fuck my way into management? Or was I just sleeping with her because I could? It seemed cowardly. It seemed like self-sabotage. It was disrespectful and fun, in the way kids gleefully throwing rocks at cars is fun. But that's the thing: When you're a grown-up, you're also expected to have the courage of your mistakes. To know the price of things. If you throw rocks at cars, you will pay for it. One of those cars will stop. Someone large and looming will open the door and get out.

Here was my (biggest) mistake: I told a woman I loved her, then I tried to keep her hidden. I wanted her enough to take her, but not enough to let everybody know. I thought if they knew, I'd be fired. Or if I weren't fired, then reviled. Oh, that kid, they'd say, he dragged his personal life into the office and made us all look at it, like a cat dropping off a mole. Looking back, this was all just a way to protect myself. Sleeping with her prevented her from being my boss, which I enjoyed, but if people knew I was sleeping with her, they would think I didn't deserve my job, or my reputation for doing good work. At the same time, I loved her, or thought I did. But that's the thing: In that situation, you can't really know. There's no fixed perspective. You don't know, at work or in bed, whether you're making love to your boss or your lover. In the attempt to maintain control, you have no control at all.

So I wouldn't let her kiss me good-bye, or hello, or leave the office with me. We couldn’t go to office parties together. Couldn’t stand too close. Couldn't tell any of my friends. When my parents called and asked who I was dating, I said, after a pause, nobody at all.

The first time it ended, after a few months, was at a restaurant. We were with co-workers and I got up to leave. She asked me not to go. Then she asked louder. And then we were on the sidewalk, clutching, scratching, arguing, for everyone to see. "I’ll never be enough for you," she said, her way of saying that me keeping us secret had been keeping her ashamed.

It’s a strange thing, for something so secret to end in such a public way. It’s a relief, in part — an unburdening. But it also makes you sad you tucked someone away for so long, and because of course everybody we worked with had always known. Like when you ran away as a kid and your parents knew where you were hiding the entire time.

A week later, she moved away — same company, up to corporate. She'd been planning the move since before she met me. I felt abandoned, and relieved, and really just bewildered — like, what the fuck do I do in the Midwest now? They shut the door to her old office. For a time, we stayed together over the phone, and then we didn't, and then we did again. I visited her. It became one of those on-again, off-again relationships. The distance let us keep pretending, I guess, that we had something real. We made an uncomfortable knot, like a root growing through a fence. 

The last time it ended, this time for good, we were at my apartment, years later, in New York. She told me how she missed those times in her office, those conference calls. "I wish we could go back there," I said. And isn't that a perverse strangeness, to want to return to that secret and hidden place, to begin again, to make it right this time? Even if that place is shabbier than you remember, and that romance the romance of a withering time.