(Part 1 here.)
Some say that the desire to be Don Draper is really the desire to live in a simpler time with established gender roles, a romanticizing the past. That's a girl talking. When a guy fantasizes about living in the Middle Ages or a different planet of Don Draper's America, they're not wishing for a different environment, they're wishing for a different movie. It's not the setting, it's the plot. No one wants to live in 500 AD; they want to be in King Arthur's court, with a certain kind of adventure, or relationship, or... they want to be somewhere where most of the plot is already known: I want that to happen to me.
Even when it's a real historical time, even one as well detailed as the one in Mad Men, what you want isn't to be alive then, but to be in that show. They want a movie in which the main character (you) already possesses a character that everyone accepts (you don't have to be like Don Draper, you are Don Draper, and everyone knows you as that kind of person), act in any way you want; and though there will always be consequences and miseries and laughter and whatever, no matter what happens it always happens about you.
A key plot point in Mad Men is that Draper's coolness and masculinity is artificial, it is an act. That's fine, everyone has an act of some kind, why not be cool? But when you choose your own act, be careful you do not choose to act like someone else who is themselves acting.
This is why, whenever someone tries to affect the style and mannerisms of a character in a movie that other people have seen, it makes the other people cringe; it always looks horrifically fake. We already know what the original looks like. If you're get on a bus to go to a sci-fi convention and are dressed like some kind of alien, you're judged by the, well, coolness of your costume. But if you dressed like an existing alien-- like a Dalek-- people on the bus will think you're an idiot. The better your costume, the more people will hate you.
It's even more difficult to emulate Don Draper, because Don Draper is already emulating something else (forget about Jon Hamm for the moment.) Draper (on the show) can get away with it because no one is familiar with what he's pretending to be (some construct in his head) so they can believe it's really him. You can't be Draper because we already know Draper.
Being someone else is very hard. Sometimes, even if you are actually who you say you are, it can still be fake. When an aging rocker tries to dress all cool and rock starry, it's creepy, because even though he is authentically a rock star authentically himself, he is still faking it: he's pretending to be who he was 30 years ago. We already know who he was 30 years ago, and that's not him now, so this impersonation is obviously, pathetically fake. Stop it.
The only time we tolerate this is if we are at an aging rock star's concert: because we're all aged by that point, and we'd all like to pretend, if only for a little while.
It goes both ways. Don Draper is 36. If you are 26, is there any way you could be Don Draper and make it legitimate? It only works if you're in your late 30s, because the game he is playing is "I've seen it all." You haven't. You can't fake it, any more than you can fake playing the guitar. It's fake. She can tell. She may not tell you, but she can tell.
"Can't I just borrow some of his characteristics?"
I know, it helps your social anxiety; I'm pretty sure no one wants to be Don Draper because they think it will help them pass a midterm. Ok, so what will being Don Draper get you?
Suave? Cool? Sophisticated? Because I've written those three words, it appears that those are three things you could copy. But Draper doesn't actually possess those three things, he is conveying those three things. He has branded himself as a guy with those three things; just as Nike has branded itself as a certain kind of shoe that isn't made of inferior leather in a sweatshop. Draper the brand is a guy with a nice suit, but that suit is a brand, too (Hickey Freeman?)
Note how uncanny it is to see him in bed in the morning, without a suit.
If you want to emulate Don Draper, you will get the same exact outcome a) if copy his persona but wear your clothes, and b) if you wear his clothes while keeping your own persona. They're all brands, they're all equivalent, and no matter what you choose the girl will figure it out the moment she purchases you.
"No, you're wrong, you've misunderstood me, I feel like you're almost giving me an answer, but you're missing something, you're not getting what I'm asking. He is cool and sophisticated. That's why he can pick up girls so easily. I want to do that, I want that secret."
You can't emulate Don Draper, and you think the problem is that I've misunderstood?
I understand you very well, I've seen you in action. When I'm in a bar-- and I have been in a great many bars-- I watch the show. Life has become so much a copy of TV that I sometimes forget to pee because a commercial hasn't come on. In one show I watched you were standing with a beer, staring but not staring, talking with your friends about things that interest you, but trying to figure out the right conversation to have with the girl across the way who probably would not be interested in those things. I saw you. I saw that there were the female equivalents of you in that bar, too, but you didn't see them.
In every case the problem is the same: you don't want what you think you want. And the type of girl you think you want sensed this the moment she saw you. That's why she was pretending she didn't see you. Or did you think hot girls have no peripheral vision?
So you want to be Don Draper? You are. No, that's not a motivational speaker's empowerment mantra, it's a sad, unfortunate truth. Or a warning, if you choose to listen.
Look at your suave, sophiticated, masculine Don Draper. He married a beautiful woman; you will, too; and like him, when you get her you won't be happy.
But forget about marriage, who has this well hung lothario seduced? Has he had affairs with sexy secretaries, bedded underwear models?
No, he's had none of that; the three affairs he's had in two seasons are a hippie artist with numerous other men in her life that she likes more than him; a beautiful owner of a department store-- hardly one night stand material-- who actually hopes it is going to turn into a marriage; and a woman as marginal as she looks. These are the conquests of the great Don Draper. Real women, to be sure, but none of them are who you'd want, right?
And in every case, these women dump him the moment he reveals to them the black, infinite, starving neediness inside him. "I need you now!" he says to his mistress. She does not mace him because it had not yet been invented.
Don Draper is that worst of all possible men. Cosmo warns its future starlets to beware the heartbreaker, but what girl doesn't want her heart to get broken by a great guy? None of Draper's conquests have their hearts broken; they have their spirits broken. He's not a cocksman, he's not a player, he's not a ladies man. He is a serial monogamist, incapable of committing entirely to one person, but similarly incapable of at least committing to the playful lightness of physical intimacy and then just taking a nap. At least she'd know where you stand. They destroy the lives of everyone around them not limber enough to leap out of the moving car. Tuck and roll, that's the secret Cosmo never tells you. Tuck and roll; but at least get out; he is driving you nowhere with a full tank of gas.
These men stay with the girl-- sometimes for years, without cheating-- but their inner eye is always on something else. No matter how desperately they think they love, they also know, simultaneously and without contradiction, that they're not really in love, and that this, too, will pass. They are immortal; there is always a future, because... because this can't be it. But they fear the future, so instead of pursuing it, they wait for it, along with the girl they've handcuffed with inertia.
These men are already Don Draper, they think because they lack his facility with gab they aren't-- but in every way that counts, at a genetic level, they are the same. If you want to see how it all turns out, watch the show.
Now maybe you understand: when a guy with moussed hair and a seashell necklace starts staring at the girl's chest and rubbing his own, it must feel to her like some kind of immense relief.