My Mad Men: When Your Boss Is Your Lover

Between my marriages I dated two bosses -- two mad men -- back to back. They weren't the "mad" of Madison Avenue. They were mad as in angry and sometimes even crazy.
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Many of us who grew up in the era of Mad Men can look back at similar office experiences.

After watching the first episode of Season Three, I reflected back on two of my own past office situations. Between my marriages, as a rather clueless new single, I dated two bosses -- two mad men -- back to back. They weren't the "mad" of Madison Avenue. They were mad as in angry and sometimes even crazy.

At the time I was unprepared for and unaware of the consequences of office relationships. Oh, boy.

Boss #1

When I was 42 and newly separated from my husband, the only man I had ever dated, I became editor at a travel publication. It was a small office, with the publisher's desk in the middle of it all. I was delighted to get this writing position and eager to please. Because my soon-to-be ex could care for my sons, I was able to travel extensively for the first time in years. And my first assignment was writing about Hong Kong and Japan.

I was in my Tokyo hotel room when got a call from the publisher. "I'm in the lobby. Come down."

I couldn't believe it. The very hotel I was in. How did he know? "What a coincidence," I squealed into the phone.

What an idiot I was. He had been traveling in the Philippines, and had detoured his trip just to overnight where I was staying. He was the powerful boss, I was the new female employee in a job that many others wanted. And he intended to seduce me.

He was 15 years older and full of himself, and I didn't want to be with him, but I loved and needed my position. There in the Tokyo hotel overlooking Mt. Fuji I was dismayed and confused, but I rationalized that he was divorced and that we would just have a one-night-stand and it would be over by the time I got back to the states. I just knew he had the power, and as a single mom I especially needed this job, which among other joys allowed me to be home in the early afternoon. Like Joan, the super secretary-supervisor who was raped on the floor by her fiance in Mad Men, I kept quiet and went along to get ahead.

When I returned from Japan, I remember the phrase the boss used when he saw me: "Welcome home with bells on." That was pretty dumb, but he obviously wanted to continue from where we left off. Again, I was stunned, obviously involved in this conflicted scenario deeper than I realized -- and I had no idea how to get out of it. I might as well have been 16 for all the dating experience I had.

The relationship lasted three years.

He was a tough boss and despite the opportunities to travel the world, many times I tried to break up, because I never really loved him. But always I knew that if I broke it off, I'd lose the editorship.

"Don't worry, I'd never fire you," he assured me when I dangled the idea of ending it. So I finally did. And of course he fired me immediately.

"You're too expensive. I didn't fire you. I just can't afford you."

Right. I didn't know about legal ramifications. "Sexual harassment" was not in my lexicon back then, nor in the public consciousness. I just knew I lost the position.

Boss #2

Soon after, I met E from an ad in New York Magazine. E's ad took up a whole column at the beginning of the personals section, and it described a man who was cultured, erotic, witty and overeducated. The only small problem was that I lived in New York and he ran a company in Washington, DC. But I answered the ad anyway, never thinking I'd ever get a date with him.

He met me on a Sunday morning in Manhattan. We had breakfast at the Carlyle hotel and chatted for hours on a Central Park bench in budding March warmth. Like my previous boss he was also 15 years older, with silver hair and a decisive manner. When he kissed me goodbye by the fountain in front of the Plaza hotel I was hooked.

He flew from D.C. to New York the following Tuesday, for a surprise date with me. I was smitten by his bravado, and eager to be in another relationship. I could not then imagine myself a solo -- I still bought into the idea of being whole only in a couple.

I eventually fell in love with E. -- his power and energy. And a year-and-a-half later when my younger son went off to college, I rented out my house in New York and moved to Washington.

And then he, alas, became my boss, too. I worked for his company and sat in an office two doors down the hall, and lived with him on and off for five years, and we intended to get married. But the divorce that was supposed to come through right after I met him was endless. ( I'll probably write about that crazy ordeal later.)

E's wife had worked in his company, and although I had nothing to do with ending his marriage, I was shunned by many of the workers as "the boss's girlfriend." It was awkward and stressful. Like Peggy in Mad Men, I needed to perform 110 percent to show that I was worthy of my "director of communications" position.

E became increasingly uncomfortable with the situation. He kept poking his head in my office, checking up on me to see if I was working hard enough. My two roles in his life collided at odd times; 24/7 with an ambitious businessman left little time for romance. When the combination soured and the relationship was ending, he became roaring mad and hypercritical, and I was terminated abruptly once again by a lover-boss.

I moved back to my house in New York, older and scads wiser, and ready for some independence. I readjusted, and started writing travel books, enjoying singledom for the first time in my life.

I had learned the hard way from those two relationships, and never mixed business and love again. And five years later I met my non-bossy second husband.

I'd had enough of mad men.

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