Here Are The Perfect Secretary’s Day Gifts For 11 Of Mad Men’s Finest Secretaries

Entertainment Features
04.23.14 11 Comments

Today is Administrative Professionals’ Day, or what used to be called Secretary’s Day. It’s the day of the year in which we honor and celebrate the men and women who put up with their asshole boss’ bullsh*t all year long. An administrative assistant handles correspondence, files paperwork, swallows a lot of pride, takes a lot of crap, acts as a sounding board, hides secrets, purchases gifts, and acts as the unlucky recipient of their employer’s insecurities. And for that, they get flowers or a gift card once a year, which is supposed to make up for 364 other days of bullsh*t.

That’s why, bosses should be more thoughtful about their Secretary’s Day gifts and provide their secretaries with something meaningful and substantive. In the case of Mad Men, I’ve taken the liberty below of finding the perfect gift for eleven secretaries who have worked at Sterling Cooper & Partners over the last six plus seasons.

Allison — Allison was Don Draper’s secretary in the third season, a woman who served Don faithfully. That is, until Don had too much to drink and impulsively slept with her after a Christmas Party, only to turn around and ignore her and avoid the topic of that night until Allison finally broke down a few weeks later and quit. When she asked Don for a recommendation letter, Don suggested that she write it and that he’d sign his name, which so enraged Allison that she threw a brass cigarette holder into a glass frame and shattered it.

The Perfect Secretary’s Day Present — A glowing and thoughtful recommendation letter, written and typed by Don Draper himself and hand delivered to Allison along with a separate hand-written apology, which is the least he can do after treating Allison the way he did.

Hildy — Poor Hildy was Pete’s secretary, but she was in love with Harry Crane and after too much to drink one night, she got flirty with Harry and they ended up sleeping together, nearly ruining Harry’s marriage. In the end, though, Hildy lied to Harry and said that it meant nothing, sucked it up, and congratulated Harry when his wife gave birth to their first child because she had some pride.

The Perfect Secretary’s Day Gift — A hug and an apology from Harry, who instead of trying to pretend himself that it meant nothing, should’ve at least admitted to Hildy that he had feelings for her but that he was wrong to act on them because he was married and soon to be a father. Some flowers, an extra week of vacation, and an all expenses trip to an exotic location might be nice, too.

Lois Sadler — Sadler is the incompetent secretary who Don took off his desk for embarrassing him, who had a crush on Sal Romano, and who was driving the riding lawn mower that ran over the British executive’s foot.

The Perfect Secretary’s Day Gift — A year’s worth of therapy sessions to overcome the trauma of seeing a man’s foot mangled in a riding lawn mower, shot out and splattered on her co-workers. Also, maybe some driving lessons.



Scarlett — Scarlett was Harry’s secretary, who Joan fired for falsifying her time card, but who Harry hired back in a fit of anger at Joan.

The Perfect Secretary’s Day Gift — The afternoon off, so she doesn’t have to falsify her time cards to go out and get lit with her friends.

Ida Blankenship — Bert Cooper’s long-time secretary who was eventually assigned to Don so that Don would stop sleeping with the secretaries. She died, suddenly and unexpectedly at her desk in season four.

The Perfect Secretary’s Day Gift — A nice casket, made with mahogany with a fine lining, plated fittings and brass decorations. Something that befits 40 years of loyal service, and a sexually depraved affair with Roger back in her younger days.

Peggy Olson — Peggy began the series as the “new girl,” Don Draper’s secretary. She’s now the Creative Director of Sterling Cooper & Partners.

The Perfect Secretary’s Day Gift — Long stem roses meant for her, and not her secretary, preferably from Stan Rizzo.

Megan Draper (née Calvet) — Megan began as a member of the typing pool, was promoted to receptionist, and eventually became Don Draper’s secretary, which led to their marriage.

The Perfect Secretary’s Day Gift — A divorce. Let her start fresh and find someone who loves her and treats her well, because that’s never going to be Don Draper.

Dawn Chambers — The first African-American hired by SCDP, she became Don’s secretary before eventually replacing Joan as Head of Personnel.

The Perfect Secretary’s Day Gift — A raise, a car service to and from the office, and some damn respect around the office from someone other than Joan.

John Hooker — Hooker was Lane Pryce’s secretary, although he insisted he was more than that, and thus requested that he be referred to as Mr. Hooker instead of John. Instead, his co-workers referred to him as Moneypenny.

The Perfect Secretary’s Day Gift — A pair of testicles.

Jane Sterling (née Siegel) — Jane was Roger’s secretary, who he ended up having an affair with and eventually marrying, before divorcing after they realized their marriage was failed during a LSD trip.

The Perfect Secretary’s Day Gift — More LSD, and an increase in alimony payments.

Shirley — Shirley was Peggy’s secretary until she inadvertently embarrassed Peggy, at which point she was reassigned to Lou Avery’s desk.

The Perfect Secretary’s Day Gift — When the time comes, the satisfaction of letting Lou Avery know that he’s been fired just so she can wipe that smug look off his stupid f**king face.

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