Sorry, I'm confused. Why does he have to do what you do? Why does he have to be pushed out of the nest? He is his own man and can do things his own way I think.
PN and I are completely different in how we date and find others... I don't even know what he does. It isn't my business and if someone comes along that is interesting and he is excited about, I know he will tell me. That is all that needs to happen. Meanwhile I do my thing, he does his. I give him advice and guidance from my own experience but he doesn't have to take it or even ask me for it... often he doesn't.
He hasn't dated since last summer and shows no signs of getting on it. He is just not into it for now... with your man, why not leave him alone to do his own flying and get on with what you want to do. I don't see how his lack of dating has anything to do with you... ?