Last updated: June 28, 2017

3 Takeaways About Game from Don Draper in Mad Men



Yeah, yeah, I know—I’m really, really late to the Mad Men party. The show ended years ago, and I just got around to watching them.

It started at the end of May, when I had a long train and plane ride ahead of me. I got my hands on the first season of the show, threw them on my iPad, and figured I’d watch them during transit. Well, needless to say—I was hooked.

Just the raw, authentic masculinity of the show made me wish I was born in a different era. Alas, there is nothing I can do about that. Nothing will change. Still, there are things this show taught me, or re-affirmed to me, that just about any man living in this day and age could learn from.

With that being said, here are 10 things I learned from watching all 7 seasons of Mad Men in a month.

#1: Don’t Fucking Apologize

Don Draper cheats on every girl, stomps on every heart, is a ruthless businessman who gives no fucks, and—is selfish, borderline-psychopathic man who never seems to change.

And yet…

Does he apologize once for it?

Not really. Even when he does apologize it’s in a clever way that says, “I’m sorry for the action behind it, but there’s no damn way I’m apologizing for being who I am.”

And there’s a huge lesson in there. You’re going to screw up, whether it be in romantic relationships, business, or whatever it may be. It’s okay to apologize when you do so.

But you can’t apologize like a dweeb. You need to be sorry that the decision or action you took didn’t work—you don’t need to be sorry that you actually took that action. That makes people respect you a hell of a lot less.

#2: If She Loves You, You Can Get Away With Murder

Again, no apologies. Don cheats on both of his wives on the show. Both times they just turn a blind eye.

He runs a harem across multiple states, all the girls in said harem know it, and they just don’t care because that’s who he is. However, there is one fatal flaw in his game—he falls in love a bit too often.

He could definitely iron out the finer points of his harem game.

A woman in love is blind. She can, and will, change her ways for a man. Even her beliefs. Even if it hurts. A girl who changes for a guy is one in love. The opposite means the guy is a pussy. Throughout seven seasons, Don never truly changes his ways in regards to women.

And they love the hell out of him for it.

#3: Failure to Separate Love + Business Will Bite You

Another flaw in his game? Mixing a bit too much business with pleasure.

The problem with being a suave player and leaving a wake of destruction is the fallout. Easy to let some girls go—harder to do when you work with them, or they’re your neighbor (and friend’s wife).

Eventually it’ll come back to bite you. Either that or you’ll be walking on eggshells. But of course—adhere to #1.

Don’t ever apologize for being a man.

PS: In part 2 of this post, I’ll be dropping some business lessons I learned from watching Mad Men. To learn the basics of online business and make your first $100, click here (it’s a free 6-part video series).

PSS: Get my FREE book about getting laid while traveling here.

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  1. Great show, I’m in Season 4 right now. Don is what you call an Uber Alpha, he has the whole package. There’s so many little things he does with the girls you could write a series of posts on it. What’s really interesting is the stark contrast between him and the other guys, there’s only a few Uber Alphas in the whole series. Last thing to put out is he isn’t afraid to get angry and communicate this to the girls, keeps them in their place.

    1. Absolutely. He does have these moments though with some of the flings that he’s actually quite the dweeb. Falls in love a bit too easily.

  2. Hey Kyle,

    Exceedingly interesting comment there by you: “He does have these moments though with some of the flings that he’s actually quite the dweeb. Falls in love a bit too easily.”

    Of course talking about the character Don Draper.

    But it is the observation that he is a dweeb for falling in love too easily that really has me, well, “troubled” for lack of a better phrase.

    See, I like falling in love. I want to be in love. But it has, unanimously 100% of the time resulted in me getting jilted/rejected by the women of my desires.

    It frustrates me to no end. I can get laid all I want, by the women I “DON’T” want! Because I don’t want them.

    And the women I do want? It is only by somehow not realizing that I want them, that ends up with me having sex with them. Later, when I realize I want them, they flee like mad!

    Any advice??? Thanks in advance

    1. I’m pretty sure you answered your own question here, Michael.

      Keep your emotions in check with girls. Give up the illusion of love.

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