The story happened to my close friend who lives and punts in Russia.
He saw a WG, booked her for a second time, but she didn't take the money. From then, she started inviting him over and that's how the relationship started. He isn't able to provide for her financially, hence they agreed that she will not exit the industry and he has no problems with it whatsoever.
In the social setting, they don't talk about her line of work etc., but with close friends they're open, and she tells about her punting experience. Great relationship, both parties are happy, and while talking to him privately, he said it's more about emotional connection and vibe with her. So i reckon to each their own, communication and personal boundaries.