It's tricky. I like spending time with my regulars. With one of them, I contribute wine, and she brings a spliff. We chill, chat, smoke, eat, drink, fuck. The meetings end up lasting for 2-3 hours. I pay for the hour, which I really appreciate. Inevitably, I get to know aspects of her real life and she does mine. We might chat every now and then between meets but nothing major. I don't know about her background but I know what she aspires to now and what she's all about now. Pretty much the same with my other regular, who is an incredible fuck and is quite open about what she uses the money for and her background. It's not one of severe poverty / disadvantage etc. I feel from these two that being a WG is, as has been said by others, a lifestyle choice. They charge high rates for what they actually do. I'm interested in them as people but avoid the emotional baggage by maintaining more than 2 regulars at a time and not seeing them too often, as well as seeing civvie girls on the side.