The story is really weird but it is possible to read it from his perspective (bolded parts added):
"But he kept asking, so I said, ‘I want to fuck you Next time.’ And he goes, ‘Oh, you mean second date?’ and I go, ‘Oh, yeah, sure,’ and he goes, ‘Well, if I poured you another glass of wine now, would it count as our second date?’”
Here he may think he is being funny.
“I want to fuck you but I don’t want to feel forced because then I’ll hate you, and I’d rather not hate you" ‘Oh, of course, it’s only fun if we’re both having fun.’ He sat back and pointed to his penis and motioned for me to go down on him.
Here he may think she is saying he was too aggressive, so by sitting back he is doing the most non-forceful move possible.
There is no way we can know if he picked up on what she actually meant and ignored it, or genuinely perceived it in a way where he was acting ok. I can understand how her perception of events would be entirely different than his. So I'm mainly blaming the writer because they are the one who sought out the story and framed it how they did, and they are the one who exploited it for personal gain.