There's a lot of things to consider about Mad Men's journey from Manhattan, NY to Los Angeles, CA. While the series hasn't been shy of taking trips to places such as Kentucky or France, they have been momentary visits. Don Draper is there with an inability to enjoy himself. He is there representing the advertising agency Sterling Cooper and cannot break protocol. He is professional and talks the same way. These are just extensions of his conflicting past, which has included identity theft and whorehouses. Towards the end of season two, there's a new city that changes everything. In "The Jet Set," Draper heads for Los Angeles with the familiar routine of attending meetings for potential clients. The conservative suit looks immediately ridiculous alongside the more liberal society that he finds. As he passes by a pool with coworker Pete Campbell, there's temptations everywhere including the general idea of relaxing in the sun and looking at scantily clad women. It is a wonderful difference from New York's buttoned up style where everyone looks ready to have a meeting even as they sleep.
This is when Draper meets a woman named Joy, whose throwaway line "Why would you deny yourself something you want?" summarizes the temptation for Draper. As he loses interest in his wife Betty, he uses some of the free love that was starting to appear. Joy's family has a casual relationship without any conservative boundaries. Compared to the Sterling Cooper ethics of the time, it is scandalous. The journey becomes a baptism into a new way of life based on this one night. We never see Joy again, but her influence remains integral.
It could also be that the show is finally being honest. Where creator Matthew Weiner did phenomenal work to cover up the New York locations that were actually shot in Los Angeles on sound stages, he decides to have more open and honest set pieces. The city is allowed to breathe and characters venture outdoors more frequently. Draper experiences the frivolous life that he wants. Despite this, his old methods of seduction aren't nearly as successful in his new environment. Everyone he flirts with rejects him, as if he is only an old man in a suit.
In the season seven opener in which a ride through the airport imitates Mike Nichols' The Graduate, it subverts the manliness of the protagonist as he is being picked up by his wife Meghan. While he has been a dominating force, the moment is emasculating as he cannot even drive to their home in the hills. It also summarizes the desperation of happiness that Draper faces, especially as the film's characters end not with a necessarily happy ending, but one of complacency. At worst, this defines Los Angeles for Draper. It is a place where he tries to be happy without fear of running into his legacy of lies that made him successful.
This is where Draper's story feels honest and has less to hide from. Los Angeles has yet to be overtaken by corporate powers. Sterling Cooper considers a west coast office. It isn't a popular notion because as coworker Pete Campbell would note, it's a nice city but he wouldn't want to live there. It is antithetical to New York's forced happiness through advertisements. It is the land of free love. It is where he experiences his greatest joy and while on a family trip that includes visiting Disneyland, he marries the babysitter Meghan of whom he's known for mere days. While she continues to work at Sterling Cooper as his secretary, Draper refuses to express any happiness around his coworkers.
Even his complicated back story gets its most honest moment when Draper meets the mother of the man whose identity he stole named Anna Draper. They have long accepted the odd situation. Due to a growing illness, Anna dies. The news is not received in person, but over the phone in New York, where his past remains a mystery to everyone. The news throws him into a drinking binge with days indecipherably passing into each other. He has lost the only person he has been entirely honest with. Still, there's very little of direct misery in the series associated with the city.
Draper changes in Los Angeles. California is where he feels most free because it is progressive and not based on competitive capitalism. He learns to love life. There's businesses forming, but they subscribe to hip new trends and features the frivolous behaviors that Draper desires. As evident by the season seven poster of Mad Men, there are psychedelic elements. He's sitting in his familiar suit, unsure if he will ever fully embrace the new culture.
While there's moments that reflect Draper's inability to escape his past, he seems genuinely happier because of Los Angeles. It serves as therapy. He can clear out his toxins. He is more open with his daughter, whose relationship had soured over time. He watches everyone he knows grow up without him. Nobody recognizes the Draper whom we first met in "Smoke Gets in Your Eyes." Too many people know him in New York. In Los Angeles, it is nothing but open-minded strangers.
Most of all, the first half of season seven ends with a certain contemplation on if Draper should move to California full time and attempt to find happiness or stay with the old hat that is reliant on younger and edgier writers but is essentially clueless. Mad Men depicts the shift of culture from conservative to more liberal. Draper is a reflection of the old times begging for relevancy. He helped to build the company but destroyed his reputation. The people he encounters in Los Angeles are youths who have yet to suffer from major regrets. For Draper, it is a perfect form of escapism. If there's one side to Los Angeles that is constantly reflected in the series, it is that of eternal youth and happiness. Draper tries capturing it in advertisements, but it is impossible. Happiness isn't something that can be pitched or sold. It's about being honest with yourself.