An omega / gamma acquaintance texted to brag about banging a "hot" escort. He then stated that she even wanted him to take her out to dinner, as if this were a good thing.

Why would a hooker want to be taken out to dinner?

I surmise that she figures she can get an extra free, possibly expensive meal at a restaurant of her choosing prior to the trick, or after the trick, when she has to eat anyway. It would also be an opportunity for her to do more intel on this guy, and maybe lock in more tricks, or figure out ways of extracted more money from him.

This guy is a push-over with really low self-esteem.

On the other hand, she could always just ask for more money and have dinner by herself. She could say the first trick was done at a discount, and then she could charge an extra $50-$150 and treat herself to a nice meal.

Although I've gone to the occasional strip club in the past, I have zero experience with hookers, so I'm curious to hear from the guys that know something about these matters.