Ironically, the only women with whom Don has a remotely healthy relationship are the ones that he's never slept with. Namely, Anna and Peggy. With Anna, he didn't have to be someone that he's wasn't, and he and Peggy have such a level of respect between the two of them that sex never even enters the conversation. But Megan? She's another story. It starts off so promising, with the adorably fresh relationship with her and his children, after the train wreck of emotional neglect that was the Betty and Don Draper Experience. But then they actually got married, and as soon as the honeymoon was over...well, the honeymoon was over. Don is at least honest with her about his past, which is a step in the right direction. But he really struggles to be supportive in Megan's desire for a career of her own, especially since she wants to be an actress, which means his wife putting herself on display for everyone else instead of just him. It's indicative of the larger generational differences between the two -- Don is of the generation that expects their wives to stay at home and have dinner on the table when they get home from work, and Megan knows that's she's capable of much more than that. Of course, the fact that Don can't seem to stop himself from committing adultery doesn't help matters, and it looks like the writing is on the wall for this couple.