What Would Don Draper Do?

Questions for Don? email: whatwoulddondraperdo@gmail.com
author here

Aug 19, 2009 12:10am

111. Dear Don Draper, I have just about no confidence when it comes to approaching women and talking to them?

I’m not beholden to the Q&A format here, but this is a statement capped with a question mark. A mark that underlines your problem.

Slow down and practice privately. Start with the ‘question’ above: when you can conduct your correspondence with clarity of thought, translate. Don’t approach women. Just have something to say when something should be said—and only then. You can consider this something carefully, but don’t compose. A simple idea will do. With failure—honest failure—the lesson alters vision and vision becomes instinct, a means of navigating your way through any conversation.

My own vision has blurred lately. Betts says I need reading glasses.

Oct 22, 2008 10:40pm


It’s nice to think that everything is a part of you and you of it. But you’re alone. And people don’t change. 

Oct 22, 2008 10:39pm

109. Dear Don Draper, How do you find peace in your daily life?

Peace is a connection, an experience of something real. While satisfying, a connection with your job, spouse or finances is not always reliable. I find the easiest way to connect or find peace is visceral. For me, it’s touch. For you, maybe a song, a taste, a view. I like to give my weight over to crashing waves, lie on the grass in the park or put on a fresh-pressed shirt and feel renewed, reminded of what it’s like to feel the world around me and not just manage it.

Oct 16, 2008 11:20am


Ignore applause.

Oct 16, 2008 11:17am

107. Dear Don Draper, I’m single and looking to hook up with the type of girl that goes out on Halloween dressed as Mystique from the first X-Men movie or another costume that only requires body paint. What should I be for Halloween?

I can’t really picture what you’re looking for, but I’m sure it explains why you’re single. Also: I’m opposed to wearing costumes for Halloween or any other occaision. If forced, I’ll wear a tux and simple masquerade mask and stand near the bar.

Oct 14, 2008 8:48am


Go with her to Palm Springs. Never deny yourself something you want.

Oct 14, 2008 8:25am

105. Dear Don Draper, My wife and I have separated. How do you select a hotel for a temporary stay?

No matter the length of your stay - an hour, a night, a month - choose a hotel as if you don’t plan on leaving. The value of rest and comfort only increases when you’re away from home.

Oct 6, 2008 3:38pm


Root for the Yankees. Bring your son.

Sep 30, 2008 9:14pm


Know the elevator attendant by name.

Sep 30, 2008 9:10pm

102. Dear Don Draper, What’s the best way to order a steak?

God I must have forgotten. Lately it’s been nothing but hearts of palm salads and whatever’s left on Bobby’s plate. Alka-Seltzer for breakfast. Occasionally I’m hungover enough to cast aside my climbing blood pressure and send my secretary out for coffee and a bearclaw. Then I think about what life was like before I met consequence and wonder if I should’ve passed on the introduction.

Sep 29, 2008 9:33am


Smile, straighten your cuffs and punch him in the face.

Sep 16, 2008 3:45pm


Write your idea down on whatever’s at hand; a receipt, a cocktail napkin, a Yahtzee score card. Never delay.

Sep 16, 2008 3:37pm

99. Dear Don Draper, I’m 24 and have a job that pays well but does not interest me. It’s also been made clear that there’s no chance for promotion. How and when should I make my exit?

You have the luxury of being young and well-paid. Take your time and sight your landing. Build up the necessary experience and savings to make the jump and, more importantly, fit in. Know that a position with the opportunity for advancement comes with a new atmosphere. Competition breeds deception, risk and cronyism. You could succeed or find that you’ve failed or no longer succeed, that you’re all alone with nothing beneath you, like a spent rocket that owes its trajectory to inertia. Some men prefer security. For me, it wasn’t a hard choice.

Sep 14, 2008 10:48am


Buy that new car without taking it for a test drive.

Sep 9, 2008 11:06pm

97. Dear Don Draper, Where do I go to meet a woman like Betty?

You can’t just go somewhere to meet women like Betts. You prepare yourself every day: work hard, keep clean and stay in good shape. She’ll come along. If you happen to see her first, you’ll be ready to make your move. And a move, in women like Betty’s case, is a kind word or gesture and always honest. Betty knows what she wants. Sincerity is only the start. Hope to God you fit the rest or she feels like a gamble.

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