Spoilers ahead! If you have not finished watching season five, DO NOT READ FURTHER.
At the start of the season Don was happily remarried to Megan, his former secretary. Obviously she couldn't continue to be the boss's secretary and also be the boss's wife, so she got a promotion to copywriter and was taught how to do the job by Peggy. Megan turned out to have a natural ability for the work, and Don was pretty pleased with himself, but Megan didn't enjoy it because her dream of being an actress was going unfulfilled, so she quit.
Don didn't know how to handle this, because he thought he had come up with a way to make Megan happy, which made him happy. He also couldn't grasp the concept of someone not enjoying the thing that he enjoys so much. Megan's ambition was something new to him, and it upset the balance in their marriage. On the other hand, Megan's departure from the agency seemed to reignite Don's passion for work, so what does that say to us?
Looking back at some of their arguments during the course of the season, it seems obvious now that her dissatisfaction with her own life was at the root of many of them. Hmm, that sounds familiar. Many people have expressed their dislike of Megan, and I will allow that she can be a bit childish and annoying at times, but their relationship makes sense to me. However, now that Don has helped her get started on her acting career, their future together may be somewhat questionable.
Roger's marriage to his own former secretary (which always seemed like a worse idea, given the even wider age difference) sputtered to an end in the aftermath of a memorable LSD trip. Roger's new-found enlightenment inspired his own renewed interest in work and the agency (and in Megan's mother), but let's not forget that earlier in the season he was buying off people left and right to do extra work for him and generally keep him looking good. In hindsight, the episode of Joan's partnership is just a far more egregious example of this behavior.
However you feel about Joan's decision to have sex with a man in exchange for an ownership stake in the agency, I got the sense that this was a sort of transaction Joan was familiar with and had quite possibly been involved in previously in her life. It may have been distasteful, but it was her decision, and she made it willingly. For a single mother, or really any woman in 1967, to reach that level of achievement is significant, and I think that regardless of how she got there, we know Joan keeps the place running; she deserves it.
Pete continued to be a whiny little sourpuss who has everything and is still unhappy. Pete has been very successful at work, but in his personal behavior he has become much more like Don. He racked up several carnal trysts this season, even making a move on an underage girl in his driver-ed class before being cock-blocked by her hunky classmate. Instead he went after the unhappy wife of a commuting acquaintance, whom we later learned was depressed and undergoing shock therapy. (I guess this explains
Perhaps the boldest move was made by Peggy, who tired of Don's treatment of her and left the agency for a promotion and significantly more money at a rival shop. I was greatly relieved when we got the scene in the season's last episode of Peggy chewing out junior copywriters in a very Don Draper way; it was the show's way of telling us that we will continue to follow Peggy's journey, which for me has always been one of the best and most important aspects of the show. And as soon as we saw Don entering a movie theater, I knew he was going to find Peggy there. It allowed Don to say the things he should have said to Peggy when she told him she was leaving, and to express his pride in her accomplishments.
Things didn't end so well for Lane, who tried to solve his financial problems by borrowing from the agency via a forged check. When Don learned what Lane had done, he had no choice but to fire him, but he tried to soften the blow by allowing Lane to resign. The shame and defeat were too much for Lane, who chose to take his life in his office for the others to discover.
Betty is much more of a peripheral character now, which makes sense given the circumstances, but she was at least able to reassert herself when Sally needed her, and showed that she can be a good mother, sometimes.
The agency is now prosperous enough to make the once-apocryphal second floor a reality, and I loved the image of the five partners standing in the raw space, looking out the windows. I wish the season had ended with that, but the final moment with Don in the bar was equally powerful.
I'm sorry that I couldn't make things work with the weekly writeups this season, but life has been just a bit unsettled of late, and that combined with some travel and some poor planning on my part. Maybe by next season things will have sorted themselves out.