Maybe what's also important is that the hospitality "relationship" grows on both sides and the customer has an understanding why the staff knows them.

I'm a regular at a few coffee shops near my home and I know the staff there "know" me - it's enough to have a pleasant conversation sometimes. But that works, because we have gotten to the "familiar face" part over a longer period and at the same time.

What the restaurant owner wants is that his staff somehow treat everyone like a regular and have spirited conversations about their life events, even if they just entered the restaurant for the first time.

The staff might even be able to pull that off, with a hefty dose of online profiling - but even then, I cannot see how anyone who isn't a completely detached business type wouldn't find this extremely creepy.