This question originally appeared on Quora.
By Rahul Shankar, Technology Consultant, KPMG
If you want a short answer -- At a personal level, Don Draper is a deeply flawed human being.
The symbolism in the show's opening credits is quite telling. It starts off with Draper walking into his office, staring for a second at all his professional accomplishments. This is when things begin to fall apart. It pictures him falling; passing by pictures of many, many women. One of the last images is that of a family, with two children; a boy and a girl. His fall however doesn't end with him crashing to the ground. It ends with him comfortably seated on a couch. Smoking another post coital cigarette. Rewind and repeat. That is essentially his life.
He lives a life that is practically devoid of any rules. He usually doesn't take no for an answer. He wants what he wants and he does what he needs to do to get it. Damned be the possible repercussions of his actions.
Some of his quotes from the first episode are indicative of this. He doesn't respect the concept of love and doesn't believe that rules exist in general.
"You're born alone and you die alone and this world just drops a bunch of rules on top of you to make you forget those facts, but I never forget. I'm living like there's no tomorrow, because there isn't one."
The one factor that stands out in Don's escapades is that like many powerful men pictured at the time he loves a domineering woman. You can see a similar tendency in Roger Sterling's behavior. Betty of course does not fit this mold and this is one of the reasons he looked elsewhere. We could talk about the fact that he was near abandoned and unloved as a child. I can see how that partially relates to his relationship with Betty. She filled in a void in his life when he needed it.
But the truth is that his needs and wants have changed over time. He cares about each one of the women in his life at one point in time. But each time he sees something more desirable he wants it. His needs have continued to "mature" over the course of the seasons.
When he was younger and starting his career, he probably wanted someone like Betty; a trophy wife. As things began to move on Don moved up the professional ladder and life got less interesting with Betty. That's when he found Midge Daniels, a hippie artist who is described best by her quote --
"You know the rules, I don't make plans and I don't make breakfast."
He then proceeded to Rachel Menken, a ambitious Jewish store owner. Moving on we see Bobbie Barrett. Married, mildly unhappy and somewhat similar in nature to Don. Bobbie Barrett even makes a passing reference to how word had got her that Don was famous for his extra-marital escapades. Then there's his daughter's teacher, Suzanne Farrell, a little different from the rest, but who still has the free spirited touch to her. None of these affairs lasted too long of course.
Some of these women actually cared for him and he did reciprocate their feeling for a brief period. Once his impulses desired something else he would act on them irrespective of who was getting hurt. I'm reminded of this quote from the Kennedy vs Nixon episode where Rachel Menken character essentially calls him out when he says he wants to run away with her.
"This was a dalliance, a cheap affair. You don't want to run away with me; you just want to run away. You're a coward!"
This captures him quite well. An absolute lack of respect for the consequences of his actions. Think about Faye Miller. He actually proposed to Megan while Faye was under the false impression they were in a relationship. I know this doesn't relate to his relationship with Betty but it is indicative of his primal nature.
Don't get me wrong. Don Draper does have his qualities that women want him and men aspire to be him. He is a genius at his work. He holds true to many of the adjectives describing him -- suave, sophisticated and highly intelligent. In spite of all his faults and indifference he is a relatively loving father who tries to protect his children from what he faced. (Think back to the conversation where he told Betty about how he was beaten as a child.) He mentors a young Peggy Olsen and generally dislikes the conniving Pete Campbell. But this doesn't distract from the fact that in terms of personal relationships, he is a highly dysfunctional human being.
Let's see how the current season and his relationship with Megan affect this. The one positive from his relationship with Megan is that he wanted someone who could be a mother to his kids. Maybe this is a sign of him maturing in a positive direction this time. I'm excited for what this season has in store for us.