During one eventful trip to California, Don dealt with his past, went to Tomorrowland, and decided that the future is now. But has he confused "looking ahead" with "living in the moment"?
So yeah, Don asked Megan to marry him.
The episode started with a meaningful conversation between Don and his supposed girlfriend Faye. He confessed that he had a terrible feeling in the pit of his stomach about his upcoming trip to California—to square away Anna's estate—with his kids. Faye knows about Dick Whitman, and knows that this trip was something of an anti-vacation. With his children in tow, he wouldn't be able to escape the reality of who he used to be and who he's become. Faye said, "Maybe that sick feeling will go away if you take your head out of the sand about the past."
But there were some speed bumps on the way to California. The Drapers' nanny Carla was supposed to go with Don and the kids to the West coast. However, Betty—the queen of misdirected anger—fired her, after Carla let Glen into the house to say goodbye to Sally.
When Henry learned that Betty wouldn't even give Carla a letter of recommendation, he began to see his new wife's true colors—how she's bristling with entitlement (in an argument with him she literally said, "I'm entitled to that!"), how she thinks of life as being a big game with sides and teams, and how she's very petty. Between her emotional relationship with a neighborhood boy, her insistence on seeing a child psychologist, and her desire to be rescued from bad situations rather than figure out a way of rescuing herself, it's been obvious for some time that Betty's behavior is beyond immaturity. Mentally, she's a child. But it wasn't until she curled up on her daughter's stripped bed, confused over why life, again, isn't as perfect as she was told it should be, that it was revealed just how lonely it is being a little girl in an adult world.
With Carla out of the picture, Don decided to convince his secretary Megan to join him on his trip to watch his kids. Unlike Faye, Megan is a natural with children, leaving Don somewhat awestruck. Having been raised by an abusive father, and having lived with Betty, he didn't seem to know that people could be around kids and still be at ease. He marveled at how Megan didn't get pissed off or even flustered when Bobby and Sally misbehaved. He genuinely seemed stunned that the girl didn't cry over spilled milkshake.
The primary reason for Don's trip was to square away Anna's estate. Her niece Stephanie was waiting at the house for him, and gave him Anna's engagement ring from the real Don Draper, saying, "She wanted you to have it. She didn't play around with that."
Before she left, Don asked Stephanie if she'd be returning to college and she told him no. He asked what her plans were and she said she wasn't sure, adding, "That's the best part, right? I've got the rest of my life ahead of me. So do you."
Don returned to the hotel and grumpily refused to play in the pool with Megan and the kids. He sat on his bed, and perhaps thought of Stephanie's parting words. He has the rest of his life ahead of him. Maybe he found that notion scary instead of inspiring.
He's been grappling with the giant issue of his identity. Who is he? What is his life? Who's life is it? He decided to quit pondering these questions and just take a big cannonball of a jump into the fun part of life.
Sitting on the bed with his kids, going over their game plan for Disneyland, and how they'll manage the Dumbo ride with Euguene around, Bobby says, "I want to go to Tomorrowland. I don't want to ride an elephant. I want to fly a jet."
That seemed to give Don an idea. He, too, wants to go to Tomorrowland. He's sick of trying to reconcile his past with his present. And he doesn't want to be on the ground. He wants to shoot for the stars. While he maybe needed Faye, he wants Megan—the girl who is competent, ambitious, and good around children. She's everything that Betty never was and Faye never wanted to be. He began buying into Stephanie's sentiment that his life is ahead of him. It makes sense that he was reading John le Carré's The Spy Who Came in from the Cold when he decided he was going to take Faye's advice and take his head out of the sand (and straight up into the clouds), as the novel deals with methods being morally inconsistent with values. Remember when Megan said, a few episodes back, that she and Don are both alike because neither of them value the sentimental?
Later, in a post-coital conversation with Megan at the hotel, he told her that she doesn't know anything about him.
"But I do," she said. "I know that you have a good heart. And I know that you're always trying to be better."
"I've done a lot of things," he said.
"I know who you are now."
That appealed to him. Perhaps more so because Megan doesn't know who he used to be. And unlike Betty, she doesn't know who he was supposed to be. She just knows who he is. And that's more than Don's ever been able to figure out about himself.
Back in NYC, Don was again pondering life at the foot of his bed.
Maybe he was wondering why Anna was so insistent on him receiving her engagement ring. He seemed to take it as a sign that she wanted him to get married. So he basically asked the first girl he saw.
Meanwhile, back at SCDP, Cassandra from America's Next Top Model Cycle 5 walked in to Peggy's office, having been again asked, as a model, to pack her bags and leave.
Instead of helping out the wayward model, Peggy jumped on the girl's inadvertent tip about a pantyhose company that was displeased with its ad agency, and managed to land the first new account in 10 weeks. But her great work was somewhat trumped by Don's big news. She was clearly freaked out by it and she and Joan had a nice little bitchfest about how stupid the guys in the office are.
BTW, Joan never got that abortion. She's still carrying the "mugging" baby she made with Roger, and she's going to pass it off as her husband's.
Don, of course, had to call Faye and let her know that in the couple of days he's been away, he fell in love with someone else. This is probably going to be in her Hall of Fame of relationship horror stories for years to come: the drunken asshole who asked her to compromise her ethics, cried on her shoulder, and then dumped her for his perfect secretary.
Speaking of perfect, Betty is finally admitting to Don (and more importantly, herself) that "things aren't perfect." Don didn't seem to realize the severity of her confession, thinking that she was speaking about her new house, rather than her new household. Still, his response fit into both contexts, saying, "So, you'll move again." Because that's what these two people know how to do—move on to the next one.