I used to go to a coffee shop near where I worked fairly regularly. I deliberately tried to mix up what I ordered every time because I enjoy trying new things. One day, one of the baristas acknowledged me as a "regular" and made a note of what I had ordered, and from that day forward, that is what they started making me when they saw me walk in. If she wasn't working, I would still mix it up, but I never had the heart to tell her that the random drink I ordered one arbitrary day wasn't really my favorite. I think at some point I appreciated being remembered more than I cared about the coffee.
I have a usual order at a coffee place on my way to work. This morning I walked in and it was already ready. not because I was expected but because the owner was just making one for herself.
You know you've made it when you walk in and they start making your drink.
When I was a big drinker and sat at my pub a lot, by the time I'd walk in and sit down I'd have a drink waiting in my spot, it felt kind of nice knowing someone thought about me.
A bar is the only place I wouldn't mind them know my usual. It was a problem when the McDonald's person knew my order. I had a busy job and they were right next door...the convince was handy. But i stopped going once I realized they knew me that well.