What’s actually interesting about this, and even about my rant of a question, is just how “nuts” operates. Don, like most of the characters, like many humans, is not lacking in introspection. But, like most of the characters, like most humans, his introspection lands him exactly where he’s always been. We search and search and come up with the answer we want to hear. Ain’t it the truth.
Don is self-searching and intelligent. Maybe “rebound” wasn’t a thing yet, but he certainly gets it, and he knows, to a degree, what that looks like. What he doesn’t know is it’s the big ones; the ones that move him; the ones that feel like The One–those are the true rebounds. Rebounds from his childhood, I suppose. He’ll always find another one; a woman he can rescue; a woman who can be his savior.
He doesn’t know it isn’t about which woman it is he screws over. He doesn’t know it’s about more than keeping it in his pants.
Diana: Can’t you see I don’t want anything?
Don: Look, I’m pretty sure I had a worse day than you. Please don’t be in a mood.
He might try listening for a change. Just once. To one of these women. Listening to who they are, what they say, and what they want.
Diana: I’m not in a mood. And you’ve never had a worse day than me.
Don: You don’t think I’ve felt grief. You knew that about me the first night we met.
Honestly nearly every line Diana utters, Don counters with an assumption or a negation.
Don isn’t in that room with Diana. It is his big fat narcissistic ego, and woman-for-whom-the-world-must-stop-turning. If he would just leave ego in the umbrella stand, there might be an opportunity for actual Don, the human, (Don, Dick, whatever), and actual Diana, who has something to say. And maybe they could have a chance.
But for now, he’ll continue to not-so-secretly mock Betty’s choice to get her Masters, all while believing he’s made his mistakes, sown even more wild oats, and that now, he is ready. Everything is status quo.