111. Dear Don Draper, I have just about no...
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...
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.
109. Dear Don Draper, How do you find peace in...
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,...
107. Dear Don Draper, I'm single and looking to...
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.
Go with her to Palm Springs. Never deny yourself something you want.
105. Dear Don Draper, My wife and I have...
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.
Root for the Yankees. Bring your son.
Know the elevator attendant by name.
102. Dear Don Draper, What's the best way to order...
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...
Smile, straighten your cuffs and punch him in the face.
Write your idea down on whatever’s at hand; a receipt, a cocktail napkin, a Yahtzee score card. Never delay.
99. Dear Don Draper, I'm 24 and have a job that...
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...
Buy that new car without taking it for a test drive.
97. Dear Don Draper, Where do I go to meet a woman...
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...
Know your assets and aphorisms well: when one is in Indian country, one needs a man who knows Indians.
95. Dear Don Draper, I'm going to finish college...
Enlist. Or pick the books and movies you like best and apply at the companies who produce them. If you have no experience, offer to work as an intern. Either way, keep your head down and work as hard as you can.
Throw that beer can any old place.
Don’t let her leave the house dressed like that.
Tell her to stop talking. If she won’t, tie her to the bed and leave.
91. Dear Don Draper, Do you have any views on men...
Yes, the same ones I have of men wearing brassieres.
90. Dear Don Draper, My college sweetheart is the...
When everything must be on her terms. Particularly if she’s in her early twenties. You’re too young to know if she’s the best you’ll ever meet. Once you leave campus, your eyes will be cursed with a better woman every day.
Always move forward.
88. Dear Don Draper, How do you feel about "Gossip...
I don’t feel a thing, but I don’t mind watching. Voiceover narration is a difficult device to pull off. When it fails, it’s grating. And while an annoying gossip columnist makes sense, it’s not interesting. There’s no twist there. Just irritation. I’ll admit bias: I take my reputation seriously. I find it difficult to connect with the fantasy of being a public figure.
Judge a secretary by her ability to keep things off your desk.
Skip out on fireworks with your family to call your girlfriend. Then head home for a glass of milk.
85. Dear Don Draper, I'm considering a long...
I like the idea of entering into any relationship with an assumed distance. A comfortable remove is a wise position. ‘Long’ sounds too far for comfort.
If you’re in a jam, call Peggy.
83. Dear Don Draper, What would you do if a...
This reminds me of yesterday: Salvatore mentioned something oddly loaded about a twat or a bird. I told him to get the door on his way out. It makes sense that I know my way around a tumbl(e)r, but this “social networking” sounds exhausting. You’re asking too much. All networks support free advertising, but that doesn’t mean they’ve lost interest in quality control.
82. Dear Don Draper, What do you look for in an...
The easiest way out. If it’s a musical, the nearest.
Say it’s an old football injury.
80. Dear Don Draper, How long until I acknowledge...
You’ll have to call for ice before too long. Ask her by name.
Tell her not to confuse this.
When you try to forget something, you have to forget everything.
77. Dear Don Draper, I'm a housewife and find my...
By chance, are you almost no help with his job? Emptiness is a good thing. For relief. Find the depressing part(s) of your day. If it’s the time you spend with your husband, then yes, leave him. If it’s the children, leave them. If it’s just the repetition, the routine of homemaking, hire help and get out of the house. Fill those empty parts of your day with something new: a...
If she says she wants you on the beach, drive her there.
You know what they want you to do. Do it. Do whatever they say. Get out of there and move forward. It never happened. It will shock you how much it never happened.
74. Dear Don Draper, My kid didn't know how to...
Never hit your children. You think loss, some pain or a bruise will teach him to mix drinks? To learn right from wrong? That’s not the way it works. He’s a kid. My father beat the hell out of me. All it did was make me fantasize about the day I could murder him. Level with the kid. When he’s treated with honesty and respect he’ll aspire to be honest and respectable.
Ask her to cancel her plans and stay in bed.
72. Dear Don Draper, I’ve been feeling a bit tired...
If you feel a burn-out coming on, take the big-money offer from a competing firm, lazily work it for a year or two and retire. Buy a boat and go wherever you can take it. Maybe you’ll catch the bug again by the time the non-compete expires. Maybe not. For me, the tired, burned-out feeling is just boredom. Sleep with a new woman - hell, try your wife.
Shove her back and hate yourself for it.
70. Dear Don Draper, Let's say Sterling Cooper was...
Let’s not - please leave Sterling Cooper out of this. Also, my reputation would not be at stake if I took this account. Rather, this account would be the stake driven through my reputation. “Famously Hot” makes me feel nothing. Fire your team and look for a job at a firm with accounts that don’t cater to bored conventioneers. Grab some barbecue in the Midlands on your way...
Dance with her in the living room.
Start Sunday with a couple Bloody Marys.
67. Dear Don Draper, How do you wear a pocket...
If I wear one at all, I use white cotton or linen squares and fold them in what’s called a Presidential fold: halved twice at right angles into quarters. And don’t be a dandy - it’s meant to be used.
66. Dear Don Draper, My friends have been...
Most changes to my drink order - which are seldom - are due to locale, not season. If I’m in an establishment with a specialty, like, say, an oyster bar or island shack, I’ll make an exception. Otherwise I stick to rye.
65. Dear Don Draper, I'm a young, beautiful and...
First you have other things to consider - the principal being your father’s money. Does your partner love that? Or your youth, beauty and intelligence? All, some or just one of these reasons is enough for most people, but a true marriage is built on a greater (some say the greatest) thing: a mutual understanding. If you’d like to see a sham destroyed, wait until you see yourself - your...
Remind the discouraged that we all work for someone.
63. Dear Don Draper, I'm a 25-year-old male and...
In most cases, I wouldn’t recommend that a virgin see a party girl, but you’re the textbook exception. Get your money’s worth. Let her show you how. Ask questions if necessary. Afterward, stop trying - never even try to “let” sex happen. Don’t just act like sleeping with your girl is the farthest thing from your mind, actually push it out. And wait until she...
Tell your secretary not to cover for you - just manage expectations.