Why Do I Like Don Draper?

Warning – This Post Contains Mad Men Season 6 Spoilers

A male friend — who isn’t a Mad Men fan — watched the Season 6 premiere with me. Afterwards, he turned to me and said, referring to Don Draper, “I don’t understand why you like this character.” As a writer, I always want to understand what makes a particular character compelling or likable, or both or neither. As to Don, for me, it’s both. The puzzle is, why? Don Draper is a womanizer, he treats my favorite character (Peggy) badly much of the time, and he’s a fraud, literally and figuratively. And yet…

Don Draper is a good friend. In many ways — and I won’t even try to count them — Don Draper’s behavior toward women is horrendous. It’s not great toward men either. At the same time, when Peggy suffers a breakdown early in the show, Don tracks her down, finds her in a psych ward (or mental hospital — I’m not clear on that), and says what she needs to hear to get back on her feet. He doesn’t tell anyone where he found her, he doesn’t ask what happened, he doesn’t ever suggest maybe she can’t handle things because she once was hospitalized. That is particularly striking given the much stronger stigma that attached to depression and mental health issues in the 50s and 60s. Don also mentors Peggy to become a copywriter despite the prevailing wisdom against women having careers. When Don realizes his artist girlfriend Midge has the potential to fall in love with someone available, he not only steps out of the relationship, he hands her the money he was going to use to take her to Paris. And Don tries to help Lane, even covering the check Lane forged and agreeing not to reveal Lane’s actions. While it’s not enough to save Lane, Don does it solely to try to alleviate Lane’s embarrassment, not because he expects a return favor. 

Don Draper loves his work. One of the first times we see Don, if not the first time, he’s drinking in a bar, and he’s working. Not in the sense of reviewing or creating ad copy or debating points with colleagues. He’s asking a server about how that man feels, what he thinks, and why. Whenever Don Draper talks with anyone or does anything, it somehow later factors into a pitch to clients. I suspect part of why Don loves his work is that deep down he longs to understand people, and he’s found a business where he’s rewarded when he’s able to do that. Which may also be why he’s most honest when he’s pitching. Sometimes it hurts him (as when he tells a client the real reason he loves Hershey Bars), but usually it’s why his ads resonate with people. He excels at expressing what people want and need but didn’t know they wanted and needed. I can’t help liking a character so good at what he does and who loves doing it.

Don Draper keeps trying. I find Don’s mix of self-deception and self-analysis fascinating. His whole business focuses on tapping into people’s needs and desires, especially the unconscious ones. His ads also often stem from his own desires and experiences. So on some level he always engages in self-analysis, understanding what motivates him and therefore other people. Yet, when we first see him, Don spends little, if any, time questioning why he cheats on Betty, whether that’s right, or what that does to both of them. Still, Don inches toward self-awareness and change. He forms two on-going honest relationships with women — with his first wife Anna and then with Peggy. (Interestingly, two women he never sleeps with, which suggests to me his issues are less with women and more with sex.) He also tells Faye the truth about who he is. Ultimately, he veers toward Megan, who initially seems more willing to accept him without question. But even that isn’t a complete step back, as he does tell Megan the truth about himself. He also plans to be faithful to her, and is faithful for some time, most likely longer than he ever was to Betty. That he goes back to his old ways isn’t admirable, but it is realistic. Change is difficult, and most people don’t even attempt it. Don Draper does. He tries, he fails, he slips back, yet he tries again.

I wouldn’t want my son, if I had one, to grow up to be Don Draper. Nor would I want to be his wife or his girlfriend (well, OK, maybe for one trip to Paris, but that’s it). I wouldn’t want him for a boss for much longer than Peggy did. But as a friend or colleague, he’d be fascinating to spend time or work with, and he’d come through in a crises.

And, yes, I like him.

Lisa M. Lilly is the author of Amazon occult bestseller The Awakening.  A short film of the title story of her collection The Tower Formerly Known as Sears and Two Other Tales of Urban Horror was recently produced under the title Willis Tower.  Her poems and short fiction have appeared in numerous print and on-line magazines, including Parade of Phantoms, Strong Coffee, and Hair Trigger.  She is currently working on The Awakening, Book II: The Unbelievers.