After five seasons of surreal, understated drama, one might be left to wonder what Mad Men could possibly do to make each of its characters even more complex and interesting. The short answer is: Elevating the show to the closest thing TV has to a philosophical examination of life. As season six opens on a woman’s belly button, Don’s voiceover reads from a passage in Dante’s The Inferno, reciting, “Midway in our life’s journey, I went astray from the straight road and found myself alone in a dark wood.” We then briefly assume that the belly button in question could belong to Don’s latest conquest in adultery, but then see that it belongs to none other than Megan (Jessica Paré). On a business/pleasure trip to Waikiki Beach, it is immediately evident that Don is far from paradise. Set in December of 1967, Megan has by now become a successful TV actress on what is presumably some sort of trashy soap. Although Don appears to be supportive, his late night drinking at the hotel bar would suggest that his dissatisfaction level has increased since the beginning of his second marriage. Promo still from Mad Men Season 6

The episode, appropriately titled “The Doorway,” is all about how, as Roger (John Slattery) puts it to his analyst, life is nothing but doors and windows and bridges and then more doors ultimately leading to nothing. It sounds bleak, yes, but fairly accurate for the generation of over 30 adults in the late 1960s. The death of Roger’s mother in this episode also serves as a backdrop for the larger motif of the storyline, which is, reconciling getting further and further away from youth and, in turn, becoming less relevant and more anachronistic. Betty (January Jones), too, suffers from an intense desire to feel relevant or, at least, somehow in control. Her attentions are focused on Sally’s friend Sandy, a 15-year-old violin prodigy slated to attend Juilliard in the coming months.

Will Fat Betty find fulfillment with black hair?

After Betty makes a highly inappropriate joke to Henry about how he should just go into the next room and rape Sandy with a gag in her mouth, she goes into the kitchen to find none other than Sandy smoking a cigarette. As the two begin to talk, Sandy confides in Betty that she didn’t get accepted to Juilliard. Betty tries to console her by telling her that she can always apply next year, but Sandy insists that she’s already too old to be a notable violinist. The two get to talking about the city and how Sandy yearns to go to the East Village. Betty assures her that it isn’t romantic or glamorous to live in poverty-stricken conditions. This later leads Betty to search for Sandy in a tenement building in which one of the runaways seethes, “We don’t like your life any more than you do, lady.” Perhaps this is the moment that causes her to continue her psychological spiral by dying her hair black—because maybe looking like someone else will make her feel like someone else.

Promo poster for Season 6

Where Peggy (Elisabeth Moss) is concerned, it was perhaps to be expected that she would begin to usurp Don as the guru of advertising and all its associated crises. In her case, a joke about G.I.s wearing the cut off ears of Vietcong soldiers as necklaces ruins an upcoming headphones commercial for the Super Bowl in which a man dressed in a toga says the line, “Lend me your ears.” Confident under pressure, Peggy solves the problem efficiently as her boyfriend, Abe Drexler (Charlie Hofheimer), patiently waits for her to finish while also helping her by sampling the product for himself. It is clear that where happiness is concerned, Peggy is quite possibly the only character even remotely close to achieving it.

Additional promo still

The persistent theme of death is continued when Don comes up with the ad slogan for the hotel in Hawaii. Presenting the clients with the image of footprints in the sand and a removed coat and tie strewn near the shoreline, Don dreamily recites the tag: “Hawaii. The jumping off point.” The two men delicately mention to Don that their first association with the image and tag is suicide. Don gets somewhat heated in defending it until Pete (Vincent Kartheiser, who is rocking the sideburn look hard this season), greases the wheels in his usual way by saying that they can come up with something else.

Reading The Inferno in paradise.

Don’s “jumping off point,” comes, it seems on New Year’s Eve during a small gathering at their home with Dr. Rosen and his wife, Sylvia (Freaks and Geeks’ Linda Cardellini). Don, who has recently come to admire Dr. Rosen after seeing him rescue their doorman from a heart attack, is fascinated with Rosen’s ability to control life and death. Watching him cross country ski through the snow to handle a hospital emergency, Don is somehow aware that he will never possess that level of goodness. And it isn’t necessarily that he isn’t good, per se, but his hollowness—his inability to embrace whoever it is he may be—is what keeps him in a perpetual inferno, a hell on earth with no escape to paradise. This much is obvious when we see Don doomed to a life of repeating the same sins as we view in the final scene that he is having an affair with Rosen’s wife.