Welp, at least we now address the elephant in the room that is the female half of our couple being basically just an escort without the perks. Can't wait for the chapter where he wonders whether her overly nice and accommodating personality is just a phony act to get him to come back.
I kind of want this to turn really dark in some ways, because I couldn't even begin to guess what'd cause a wacko like her to consider compensated dating of all things as a part-time job. That's not a low hurdle I'd imagine, when less socially dangerous stuff like waiting tables or whatever is on the menu.