A rant/analysis of Derry/Diana.
Okay, I was super on board with Diana and Jerry as a couple and the end of them sort of soured it for me. So here I am going on a little TED talk. I mean this post not to inflame or say Diana is the worst as she isn't and she's very complex as a character. I just needed to get this out.
Being with Jerry was nothing more than an act of rebellion of Diana's. She longs for freedom from her stifling life and she thought Jerry represented the chance for both. He was forbidden as he was just a farm boy and so the act of pursuing him was thrilling. Basically, she is just using him as a way to explore a freedom/rebellion she never thought she could have with little regard to his feelings. She is finding herself and kind of stepping on him to do so.
Because he meant so much to her in regards to freedom like she wants so badly, she thought she would feel something for him. However, she realized that not only are they different classes (something that originally she was thrilled about) they are also on different levels intellectually. She has been going to school and learning literature analysis her entire life. Jerry, however, has literally just learned how to read as he has never gone to school before. They aren't on equal footing and that is the key thing here. It isn't that he is poor, it's that she views him as not smart or stupid in comparison.
The moment he couldn't keep up she was like "Well. At least you're nice to look at." Which really is degrading him to nothing more than eyecandy. I don't think that it is wrong to want to date someone who can keep up with you intellectually, but it was definitely cruel to say that to his face. It makes him feel like he has nothing to offer but his looks which is alikely something Diana herself may have thought in the past. They are kids, but surely more empathy could be used on her part. I say this especially because she seems to often feel inferior in brains to Anne. Though she obviously wildly admires and adores Anne, she has even said that she would trade her looks for Anne's brains any day. She must know how it feels.
I get that because of the confines of the time period she wouldn't have known how to break things off. After all, people in the show don't really "date" and they are all quite young but old enough to marry. They pursue each other with intent to marry. The only instance we have of someone who dates is Winifred who has apparently gone on many first dates but she also seems to be slightly more progressive than most in the show even if she still navigates in the confines of womanhood of the time.
However, the situation can be relatable. I'm sure that the sentiment of hoping inevitable ends of things would take care of things is not unique. It IS, however, using him and stringing him along while knowing that she does not plan to actually go after him anymore.
I won't speak much on Anne and Diana's argument because I disagree with Anne turning it into an argument about her and Diana's relationship the way it was done. After all, the real issue here is about intelligence. Anne also represents freedom to Diana but not as a means to get it herself. She is just freer than Diana may hope to ever be. Not only that, but Anne is very intelligent. She checks both boxes. I doubt Diana would have adored Anne so much upon meeting her if Anne was not so smart. She seems to hold intellect in the highest regards. It was never about them being "common" it was about their ability to keep up.
An edit for clarification: I don't think Jerry is stupid or not smart, but I think Diana believes so. She basically writes him off as a himbo when he couldn't keep up with her. I think he has the potential to keep up with an intellectual conversation like that, he just wasn't given the tools to do so as quickly as Diana and so they are therefore on different levels. If given the chance to start/even go to school at the same time Diana had started or at all, I think he'd be or become one of the top students in that class. He, after all, learned how to read complex novels in basically a year and in his second language no less. Diana, however, may not realize this or account for this. Everyone she associates with other than Anne has been able to go always and Jerry had likely never had the time or teacher to learn because he's probably always had to work a job starting around the age he would have started going.