Secretary Hulton Archive/Keystone
By Amy Phillips Penn

VINTAGE GOSSIP is alive and well in the elegant hands of Amy Phillips Penn, former society columnist for the New York Post.  Every Thursday, Amy pens her posts with that same touch of class, making the legends and lore of a bygone era as relevant today as they were when Jackie O was queen of New York.


Why it is that whenever a man takes you to lunch around here,
you’re the dessert?” — 
Peggy Olsen, Secretary (for now), Mad Men


Sometimes I wonder why I bothered going to a competitive college.

Diploma aside, I went straight on to secretarial school (Betty Owens) so that I could type my way into my dream job. I had never owned a typewriter, and didn’t know an electric from a manual — or even cared.

Then there was carbon paper; ugly messy, bluish-black paper that was inserted between sheets of spotless, white paper to make “easy” copies. The pressure was on. There was no room for even one mistake unless you chose to retype the entire page.

Then slowly, typing progressed one miracle at a time: from Wite Out, to the magic “x” key on the electric typewriter that erased an imperfection-gone-malapropism and substituted an instant, manicured correction.

After my secretarial course, I went to Conde Nast to take a typing test, a requisite for a magazine job. Tests make me nauseous. I was sealed into a closet with a grown-up highchair and a monstrous manual typewriter. My task was to type fifty words a minute with a minimum of mistakes. Somehow, it happened.

I was elated. My dream of working at an exciting magazine was looming large, or so I thought. I hoped for a job at Vogue, which never happened. My peacock feathers would never fan in couture.

I phoned Condé Nast to see when I could start. A woman with an affected “I work at Vogue and you don’t” voice returned my call.

“We must wait for the perfect match, the ripe occasion to blend you into the soul mate of jobs. Think of yourself as a tree waiting to blossom into an exquisite partnership.”

Vogue editors were rumored to make around two hundred dollars a week.

Were secretaries granted a few subway tokens and throwaways from last year’s season?

How were you supposed to survive and be well dressed at the same time?

Not content to wait for a nonexistent job to ripen at Condé Nast, I signed on with GQ (then owned by Esquire). My name was soon on the masthead, with a title that included the word “editor.”

I did my share of typing, shopped the men’s fashion market, worked at fashion shootings (which meant getting up at some obscene hour of the morning) ironing, and dealing with a lot of attitude.

The movement for secretaries was gaining strength. We were now called “assistants,” a term which was not easily adopted. “Secretary” was ingrained in our vocabulary, as was the image of the efficient, savvy, well dressed gate keeper.

Enter secretaries with benefits.

It happens all the time. They’re all just between marriages, you know that.
He’ll probably make her a copywriter. He’s not going to wanna be married to his secretary
— Joan Harris, Mad Men


The secretaries who marry their bosses rarely remain secretaries for long: Bergdorf’s and Chanel, their new imprint that no tiny “x” can erase. An air of power and achievement defy anyone asking them for coffee in a superior way.

Rumors of secretaries having affairs with their bosses make office headlines faster than any typewriter can spell them out, as do innuendos of paternity identity.

Start with your keyboard; you never know what kind of future it will spell out for you.


“Millionaires are marrying their secretaries because they are so busy making money
they haven’t time to see other girls.” — Doris Lilly


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