I Dated A Don Draper

Women may be drawn to the Don Draper types, says Christan Marashio, but he’s an illusion.

As he left my apartment he said that he didn’t want me to write about him.

“But if you do write about me…” he tossed over his shoulder in his crisp British accent, “…call me Don Draper.”

He was referring, of course, to the lead character in AMC’s prolific series Mad Men. Forget Mr. Big. Now women are scouring their city for the fiercely arrogant but self-loathing creative head of Sterling Cooper Draper Pryce.

That should have been a huge red flag to me. Any man who identifies with a television character infamous for his duplicity, arrogance, and fragile ego should be avoided. But as many of us are wont to do when we meet a Don Draper type, we’re too dazzled by their supposed charm or sophistication to pay attention to the warning signs.

I remember being initially captivated by my Don’s career. He would speak of film projects he worked on and refer to actors by first names as though they were close friends. I found his vague job title puzzling but not problematic. It wasn’t Director or Producer or even Manager of Something. That, too, should have been a tip off.

While out of bed Don was cloaked in mystique, in bed he was completely transparent. Once his clothes were off, his submissiveness shocked me. His moves were tentative and hesitant. While I wouldn’t categorize him as clumsy, he was clearly unskilled and inexperienced. This was incongruous to his claim that friends often came to him for dating advice because of all of his relationship experience. 

I’ll never know what our encounters were truly like for him. He would say complimentary things and send arousing messages, but that’s where Don Drapers truly excel. They are master wordsmiths. They are so skilled at crafting a message that you become blind to the lies.

You could date a Don Draper for months and never know the “real” him. Their ability to compartmentalize is crucial for carrying on their ruse. The whole reason they create this character is to mask who they really are. I once compared his constant need to be mysterious and reveal nothing of substance about his life to that of an international spy. He took that as a compliment.

In December 2010, the time of our last go-round, Facebook made one of their many layout changes. In the process they tampered with user’s privacy settings, unlocking pages and albums that members had set as private. For the first time in the three years since I met him, I finally had access to Don’s online world. There were no snaps of him out at a trendy bar holding an Old Fashioned, a gorgeous woman on his arm. Instead I saw photos of his cat, awkward looking shots of him singing karaoke with his friends, and pictures of Iron Man memorabilia.

Don Draper was a nerd? That didn’t compute. His Twitter stream made it sound like he ran in enviable social circles, with days spent on penthouse rooftops and nights out in the Meat Packing District.

As it turns out, his job wasn’t as glamorous as he made it sound, either. He wasn’t rubbing elbows with Hollywood elite. His job was an amalgamation of grunt work and various other modest marketing responsibilities.

This guy wasn’t Don Draper. He was Pete Campbell—immature, defensive, and always posturing.

“Everyone makes mistakes, but the fact that you’re the kind of person who cannot accept blame is egregious,” says Joan Holloway.

Don had asked me if he could pen an essay for my website. In it he detailed the value of relationships and how much he had learned from me. Two days later, after one of our tense back-and-forths that had come to define us, I received an extensive missive from him explaining why we wouldn’t be seeing each other again. “If a month were to pass and we didn’t speak, I almost certainly wouldn’t contact you,” he said. Ever the polite Brit, he closed with, “I wish you well.”

There is no such thing as a genuine apology from a Don Draper. They must cling to the moral high ground at any cost. At best they offer a non-apology. It typically goes something like this:

I’m very sorry if I caused you some profound hurt. I don’t quite understand it but…

The “but” loosely translates as “I may have screwed up…but you screwed up too.” That’s not an apology. That’s an attempt to shift the blame. Like Joan said, Don Drapers will do anything to avoid being accountable so that they can keep their flimsy sense of righteousness intact.

In the early summer of 2011, when all was said and done with my aforementioned Don Draper, he typed up a 1,500-word message attempting to make amends. Despite what I had thought, he assured me that he did not consider me some mistake that needed to be erased and didn’t want to forget me. I thanked him, finally feeling like he had taken ownership of how poorly he had treated me and wished him well. Three weeks later I unblocked him on Facebook, reversing a childish action that was originally borne of anger and hurt. A few days later, having made no attempts at conversation or contact since accepting his apology, I made the mistake of trying to pull up his Facebook page.

He had blocked me.

With the click of a button he erased all the good will he had generated. He said he blocked me because he read a recent article I had written—that had nothing to do with him—about Facebook and how the social media platform had complicated break-ups. He closed his explanation by saying that his decision wasn’t personal (Huh?). He saw nothing confusing about the polarity of his behavior. There was no point in trying to explain to him why, again, I felt humiliated and foolish.

Introspection is not in a Don Draper’s vocabulary. The one thing they staunchly refuse to do is look inward. They can’t, because doing so awakens their guilty conscience. That is what eventually does them in. They become paranoid that their worlds will collide and their lies will be revealed.

I have theorized that Don Drapers are inexplicably drawn to, but terrified by, a dominant woman. Their desire to fuck her is almost as great as their desire to break her. They resent her refusal to buy in to their charade. The closer she gets to ripping off that mask, the more trapped Don feels.

It took me some time to figure out why this relationship scarred me the way it did. There was never any kind of emotional component to it, no affection or care. He had treated me like I was disposable and didn’t matter. Which, truth be told, is the very thing I tell myself in my deepest moments of doubt. That was the trigger. The shame I still at times feel for trusting him and so desperately seeking his approval sometimes overwhelms me.

I think many of us have those experiences that we carry with us in our dating arsenal. The ones we refer to or use as a blueprint. My experience with Don taught me a very important lesson: The red flags are always in the inconsistencies.

While a guy with a sexy accent is still my weakness, I know now to look past an impressive exterior. Beneath that tailored suit often beats the heart of a profoundly insecure young boy struggling to become a man.

Christan is an NYC based writer and columnist. Her work and advice has been featured in media outlets such as Match.com, YourTango, MSN’s GLO Network and The New York Post. You can find more of her work at And That’s Why You’re Single. As a 40-something dating in Manhattan she can teach you that sometimes the love of your life is the love of your life. Follow her on Twitter at @ATWYSingle

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