If you really want a long response: he was raised mostly by a single mother who was so insane and controlling she really did a number on him. His dad, who was around at least but did not have full custody, was a total betamax despite looking more than a little like Sting.

I'll give you a super brief example of his mother's behavior: once he washed his hands in a theater bathroom and was freaking out because he was headed home right after that. The soap was very floral scented, and he worried that she would think he was doing drugs when she smelled his hands. I stopped him, "smells your hands? Why would she be able to smell your hands?!" He told me that she does that to see if he's been doing "things he shouldn't." Which probably meant more than he realized at the time, and grosses me out now.

So he's always had a preference for girls who direct the relationship. This one is probably the worst in the feminism department. She works for an non-profit and is very wealthy. She comes from a household with an extremely beta father. And she has no grip on what reality looks like. If they didn't spoon feed it to her in college, she isn't interested.

(Aside: she and I have had the women vs men earning rate argument, only because I wanted to rile her. She couldn't accept those numbers either, and we pulled them directly from the BLS.)

So that's your answer. He is with a girl who is roughly as controlling as his mother, just in different ways. He's seen my success with women over the last few years, and listens to me to some extent, so he isn't totally averse to the red pill ideals. But he constantly says "I don't want to do it that way." So he gets what he gets. I'm hoping this one is crazy enough to make him reconsider.