Don Draper: Ladies’ Man in Crisis

by GK on August 17, 2010 · 7 comments

I’m about to do something I never thought I’d have to do: give Don Draper advice on women.

If you’ve watched “Mad Men,” you’ve watched one of the most fascinating characters ever to grace a TV screen. On one hand, Don Draper is an inherently unhappy man who is honest with almost no one, including himself — yet what guy hasn’t wanted to be like him?

A season ago, Don was being lured into his own hotel room by this stewardess. What happened?

Sure, Draper might be living a lie, but through the first three seasons it was one glorious lie. His air of mystery confuses us, but when combined with his status and looks, it makes women come to him — no easy feat in the early ’60s.

But our favorite womanizer hasn’t been closing the deal through the first four episodes of Season Four. He’s making the kind of clumsy passes  that a college freshman would scoff at, he’s getting slapped around by a prostitute, and he’s drunkenly passing out on his couch every night. What happened to The Draper’s mojo?

Here’s my take on Don’s personal problems, which are not too different from what your average guy coming off a breakup might go through (watch out for spoilers):

This is what it boils down to: Don’s had an identity crisis throughout the series, but it’s much worse now. His wife stayed with him despite his infidelities, but once she learned he used to be Dick Whitman — just a poor, uneducated farmboy — she dropped him cold. In a brief moment of honesty in Episode 3 of this season, Don conceded, “I could tell, the minute she saw who I really was, she’d never want to look at me again. Which is why I never told her.”

Ouch. We may not all live under hidden aliases, but I would say we hide certain parts of us from those we care about or desire. Having our deepest insecurities aggravated by a heartbreaking rejection would hurt any man’s swagger.

And swagger is what Don is sorely lacking right now. The abandonment of Dick Whitman has bled into his Don Draper persona, which was once indestructible. Women once looked at his suit and his bravado and saw an elusive prize to be wooed. Now, he’s just another aging, drunk, divorced guy.

In the season opener, we see Don on a first date for the first time, and just like any dinner date, it looks awkward (although she clearly wants to see him again).

At least he looks dignified in that encounter (despite his failed attempt at getting into her room). But with the women who have followed, he’s been a clutz. His attempts at seduction have amounted to little more than lame come-ons like “You’re so beautiful … and young,” and the only girl who has fallen for it has been his secretary — secretaries, by the way, would have been beneath him a season ago.

Contrast that with the above clip from Season 3, where Don is on top of his game and effortlessly seduces a feisty teacher. This wasn’t a sudden move, either. Don had taken time getting to know her and building up the sexual tension. Then, when he saw his chance, he took it without apology. (And guys, consider this a great verbal and non-verbal demonstration of how to hold your ground with a woman.)

Don’s air of mystery has been punctured like a piñata, and perhaps because he’s suddenly so available, women are making themselves less so:

  • When he offers to walk his date up to her room, she says, “No. I know that trick.”
  • The blonde psychologist in the second episode manages to reject Don’s dinner invitation and sum him up glibly: “Don’t worry, you’ll be married again in a year … I’m sorry, no one wants to think they’re a type.”
  • The 21-year-old in Los Angeles has him pegged from the beginning and shoots him down in the car. She also delivers this gem about dating: “Nobody knows what’s wrong with themselves … and everyone else can see it right away.”

So yeah, these are dark times for our hero. But a comeback is not far away if Don gets his act together. Here are some free tips for him:

Pick an identity and own it: Whether that identity is Don, Dick or some new guy.  Though he’s vocal about his distaste for self-analysis, he is going to have to know himself better — because women are catching on to him quickly. He may not like being labeled a divorcee, but that is how women are going to prejudge him from now on.  

Get your sensitivity back: For all of Don’s alpha-male conquests, and there are many, a key weapon in his lady-killing arsenal has been his sensitivity to women. He spent an entire episode in Season 1 trying to figure out what women want, he was the only person in the office to notice Peggy’s new haircut in Season 2, and when he got caught cheating, he saved his marriage to Betty (albeit briefly) by writing her this tear-jerker of a line: “I understand why you want to go on without me, and I know you won’t be alone for long. But without you, I’ll be alone forever.”

This season, Don has been almost universally clueless to how women think.  I’d say we were all meant to be appalled by Don’s callousness with his secretary after their hookup, and it culminated with her smashing up his office and walking out. And this time, Don didn’t even have the heart to finish his apology letter.

Regain the Draper Mystique: The best part of Don’s seductions is that he isn’t always the one doing the seducing. In Season 2 alone, Bobbie Barrett and that hot jet-setter in L.A. played the cat to Don’s mouse. Even his wife would stare at him while he slept and whisper, “Who’s in there?”

Now, Don’s idea of being a challenge is giving a girl he just met the reach-around. He’s still a star in the advertising world, and he still dresses like a million bucks — it’s time to act like that again.

Lay off the booze: Maybe it’s just getting older, but the mid-day Scotch sessions are taking a toll on him. Even his self-destructing secretary derided him as a drunk when she quit.

Consider being more than a player: This could make the show a lot less exciting, but it might be the best thing for Don. As down as he is right now, in a way he’s been liberated. He’s out of a frigid marriage to a woman who couldn’t understand him, and he can go one of two directions: continue to bed multiple women in a fun-yet-superficial way, or take the opportunity to find something he’s never found: a meaningful connection with a woman who loves Don/Dick for who he really is.

Could that woman be the very blonde who predicted he’ll be married again, and with whom he has shared office tension this season? Could be, but regardless, I want the old Don back.


1 Telematic Dan! August 17, 2010 at 12:28 pm

Nice article, Greg.

Did you notice in this last episode how shaky he was when he took the belt of whiskey after Allison ran out? It was easy to miss because the attention was on Peggy’s head peeking over the office wall, but he definitely NEEDED that drink. We haven’t seen that level of weakness from him before.

I’m seeing a lot of mentions online that people are worried that Don has become boring and the character may have nowhere to go. He’s become a parody of himself, or at the least, boring. But I’m confident it’s just a period in which the writers want to establish he’s hitting bottom and he’ll be back on some more interesting plotlines soon. It would indeed be very interesting to see him interested in one woman that challenges him, like Rachel Menken or Bobbie Barrett.

I’ve always thought they’d bring back Rachel at some point. She was the only one who really got him.

And it just occurred to me: he’s become Roger from Season Two. Alcoholic, fooling around with secretaries, blind to his own problems that are totally apparent to everyone else…right? He totally judged Roger for that and distanced himself from him, so it’s interesting to see now that they have flipped but Roger has more empathy.

In closing, there is one new hot mama in Don’s life: Miss Blankenship! Can you do a seminar on how to pick up a crusty old Brooklyn dame who is hard of hearing and wears four layers of wool even in the summer?


2 GK August 17, 2010 at 12:46 pm

I had to look again, but you’re right about Don being shaky for a drink. I have a hunch he hasn’t hit rock bottom, either — like Roger, his health may be about to take a hit after all that abuse.

I absolutely think Don has somewhere to go, though. He can become Don 2.0 — all the charm with half the self-loathing, and with a real relationship.

Rachel would be great for Don, but I’m rooting for the blonde shrink! Imagine the mind games they could play on each other.

I’m not sure exactly how to pick up Miss Blankenship, but it must involve a warm glass of milk and long nights of bingo. She and Don could be a great comedy team.

3 Tre Tre August 19, 2010 at 12:05 pm

GK, you’re a smart cookie. Good to talk to you about this last night. I have some thoughts to piggy-back on your sage advice.

I cannot emphasize how much giving a woman inattention can drive them to outright hatred of you. A little strategic withdrawal to create some tension can be called for, but anything prolonged will have that woman digging deep into her insecurities and she’ll lash back like

Early on, Don was mysterious. He sat upright, sipped from his Rye, smoked his cigarette and looked his target in the eyes. His targets, in turn, prattled along and sought to get inside this man of mystery’s head. Just at the precipice of this wonder, Don would turn soft and empathetic, and the next sound you heard were panties hitting the floor.

Next, a big turn off is when a woman feels like someone assumes that they are their’s. This isn’t confidence; it is conceit and can kill the mood in the same way two improperly digested burritos would. Conceit is insecurity and insecurity is repellent. Just as you want your target to make an effort, she needs to see you making the effort to winning her over.

Don was once in a boring marriage with an attractive woman who had the personality of driftwood. When he had his mojo, he LOVED the ritual of seducing a woman. He was bored as hell at home and the game these women were playing with him gave him excitement. Don is now so self-absorbed that women just see themselves as a means to an end.

Piggy backing of the last comment, Don has forgotten the give-in-take in human interactions. This is relevant for him in work and at play. At one time, he listened to his clients and their needs, now he demands subjugation. His only card, “his brilliance,” has become a one-way street. Whereas he can bully his office workers, he cannot bully people that retain the choice and need to feel like he is listening to them. The interaction with Conrad Hilton demonstrated that Don has forgotten what made him so brilliant in the first place. He was once subtle: asking “Negro” bus boys why they smoked the cigarette they did; now it’s a bully on the playground shouting down to a “bunch of prudes” that the reason why they aren’t selling enough bikinis is because they won’t listen to him.

4 GK August 19, 2010 at 2:21 pm

You really HAVE caught up on the whole show, Tre Tre! :) Outstanding analysis. Don’t gotta learn how to listen again.

5 Andreas August 21, 2010 at 2:26 am

You are a great writer Greg, and this is the only pick up blog I need. Mad Men is my fav show and I really enjoyed this post. Keep them coming. Karma points from Norway=)

6 Tre Tre August 23, 2010 at 1:47 pm

Um…is our boy Don making his way back to redemption? Not saying anything more, but did you see what happened this week?

Episode 5 is sne of the best episodes they’ve written, imho.

7 GK August 23, 2010 at 7:14 pm

Andreas: Thanks a lot! I’ll take all the Norwegian good karma I can get.

Tre Tre: I had the same thoughts myself! I’ll write a blurb about that in a day or two. Go Don Go.

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