I've learned to only go out of my way because I want to, not because I think he'll take that into consideration. I also will no longer let draining clients carry on doing it, I inform them and will stop seeing them if things don't change. I saw someone who would always invite me for a meal after each and every session, working it into the conversation every time. He boundary pushed in other ways, always encroaching. I'd made it clear I had other commitments for my time, and much of the time a meal wouldn't be something I'd chose to do in my free time, even with closest of friends.
In the end I told him I was fed up of asking him to not do things, as quick as he'd stop doing one thing, he'd push in a different way - things such as serviced that I'd already made clear were not on the cards.
The regulars I do see are great, no pushing, they book, pay, enjoy their time with me, leave without fuss. It's brilliant.