Definitely when I'm eating out alone I like it when he/she says they remember me from last time...it makes me feel more welcome and perhaps reduces the loneliness factor. There's a couple places I go to where that happens sometimes.
But I realized recently that if I am with dining companions I'd sometimes feel funny if the server said they remembered me from before. I went for lunch recently with a former coworker and I noticed that the guy who brought our soup had waited on me once before. I don't know if he remembered me or not but oddly I found myself silently praying he wouldn't say anything about my previous visit. (He didn't--either he didn't remember me or he decided not to "intrude" because I was with someone else--see my question at the end).
This might be because I know what my dining companion is like and if the waiter had acted like he remembered me I was worried my friend would have thought, "WTF? Why does John know this waiter? How often does he come here?" My former coworker doesn't eat out much.
Are my feelings about this normal? Also, I'm curious, is there some sort of unwritten rule among servers that says they shouldn't personally greet a familiar customer if the customer is not alone?