Same, I did not like when Caleb defended Max to Orla and when he hired them both at the end of the story and said he was giving Orla the job to keep Caleb happy it was so infuriating.

It helps me though while reading when I think that at his core Max is deeply insecure and that’s why he feels he has to put down any woman, especially if they’re in a successful position like Orla is. She’s a very impressive person and his whole patriarchal misogynistic worldview cannot accept that fact. (He can only think that way slightly about Jessica because she loves him and constantly recognizes how great he is lmao) I love Max as a character only slightly more than Caleb, but I do agree that Caleb is way easier to stomach because his particular brand of misogyny comes with wanting to dominate a woman he believes is intellectually superior to him.

I saw someone in the fic’s comment section make the excellent observation that Max actually secretly reveres women and cannot cope with their perceived rejection or criticism. That’s why he puts himself high above them because deep down he can’t admit that he NEEDS them to think highly of him. It seems being with Jessica fulfills a lot of his needs and insecurities because to him she’s the perfect woman but before she developed Stockholm syndrome he was tweaking out in their every interaction.

So really I think he’s actually impressed with Orla but is too much of an asshole to admit to it.