I am known as a regular in a couple of places but they all know better than to guess at what I might order.
When I didn’t work from home it was common for the wait staff to know me. I am courteous without being too friendly and I tip well. When I was in the hospital two different places had a card for me when I came back. It is always nice to be well-thought of.
I’ve had many places where they know me well. The only real problem is when they assume your order and bring it to you when you really did want to mix it up that day. I always feel like a jerk when I send something back (usually just a drink or something) that I’ve ordered 100 times.
Generally I don’t mind being recognized as a regular. I had one owner take it a little to far as being chummy chummy with me though while I was eating to the point it made it uncomfortable eating there so I stopped going. The conversation was fine until it got to the subject of him telling me about his affairs, cheating on his wife, the fine hash he smoked the other night etc… Then he asked me to go out with him and his buddies after work one time, hmm no thanks.
I used to work in a Restaurant for 5 years, so If I find a good eatery I’ll be a repeat customer who tips well.
I hate it. To quote a great writer, (paraphrase, actually), “When the staff knows what I want, it’s time to start buying my bread somewhere else.”
I just want my order, no chit-chat.
Joe
I go to a taco place every Saturday. I’m inevitably the only gringo in their and the staff always seem to dissolve into fits of giggles when I try and order in my hilariously awful Spanish. They always get the order right, however, and I don’t complain at the 83ȼ price tag 
I can relate to this. The worst is being asked ‘Where have you been?’ if you haven’t gone in for a while. I don’t mind being greeted warmly, and I do try to support smaller businesses and restaurants, but I hate feeling obligated to do it (or guilty, somehow, if I don’t, as if my business is supporting the whole thing).
I do like knowing the bartender or chef of a successful place, on a personal level and outside of work. Those perks are okay. Not quite the same thing, though.
Recognizing my face and knowing my order is nice. I don’t care if they know my name or not though.
The baristas at the not-Starbucks near my apartment got used to me last summer because I had no internet at the apartment (just not there long enough for it to be worth it) because I came in every other day or so and ordered the cheapest non-coffee thing on the menu: iced tea. Then I’d sit around for a couple hours and surf the web, so they eventually got to the point of giving me free refills (I mean, I’m not there for the tea, but I’ll take the refill) and day-old bagels as they closed up. Never knew their names, nor they mine, but they did know my order, and it was handy to have it ready by the time I got to the front of the line.
I like it. My boyfriend and I have one local place we go to once or twice a month for almost 8 years now. It’s not terribly often, but we tip well and we’ve been going since the first 6 months or so they were open. The staff is friendly but unobtrusive which is just the way we like it. They know my usual drink is an Arnold Palmer but they’ll always ask before they serve it.
ETA: I think we’ve been there through about 3 different sets of waiters now.
I don’t get the entire “I don’t want people to know my order or face or anything about me” stuff.
I used to go into the same 7-11 for an obscure brand of cigarettes, 2 or 3 times a week, for months. It got to the point where the guy would just automatically put a pack of them down on the counter when I walked in. One time a new employee there asked me ‘you want… what kind of smokes, again?’ and my regular cashier guy who was putting things on a shelf went behind the counter, found a pack, tossed it to me, and told the employee, ‘she’s buying Magna Lites, code # blah blah’… I go through the bank drive through twice a week, like clockwork. If I go inside, the tellers say, ‘Sali! I didn’t recognize you without your car around you!’
I love it. In certain food places in our mall, the employees know me so well that if they see me in line they just start getting my order together. My orders are usuall small so if I actually want to change, they’ll not have gotten anything extra ordered up.
In a lot of cases I have found that you start getting worse service when you become a regular. I think the staff starts to think of you as somebody who is always there, like the furniture, and that they don’t have to take as much trouble to please you as they would with a new customer. So eventually you have to find someplace else to go, and the cycle starts again at the new place. This isn’t a problem if the staff turnover rate is high enough.
I’m a regular at a few places. In one place, in particular, the servers say “Iced tea?” as they seat me, and then ask if I’m having my usual. They know that I will wave away the butter and warm fresh corn tortillas, and the chips. It’s not that I don’t want those items, but rather because I want to restrict my carbs. The servers seem to treat me as a very valued customer, in contrast to Manduck’s experience.
In another place, some of the servers know that I want some spearmint in my iced tea.
I’ve found the exact opposite at a place I’m a regular at (though nowhere near as regular as my friend who works next door and eats lunch there almost every day). The staff seems to go to extra trouble to see that we always get seated together and right away. They show us their holiday pictures, we send them postcards from vacation.
There’s an awesome 24-hour greasy spoon about 30 minutes from my house. When I’m delivering in their area, I’ll always make it a point to stop there for lunch. Nobody there knows my name, but they certainly recognize me. And it’s sort of amazing/comforting to know that I’ve been seeing most of these waitresses there for approximately the last 7 or 8 years.
When we go out for a curry, we always go to the same restaurant and the waiters know us by sight if not by name. We always get a really good table, the service is excellent and the food is terrific. They don’t presume to know our order though, because we like to try different things so although they probably know that he perfers pakora for a starter and that I have rice rather than naan bread or chappati, they won’t know what else we’re going to order.
When I was working away from home for some months, I had a regular round of restaurants and pubs. And when I walked in the door, they’d pour me a pint of my usual tipple. Very nice. They didn’t go so far as to presume my food order, though.
I go with one of my workmates to a restaurant where we share a bowl of Beef Rendang, a pot of coconut rice and a jug of iced water. When we walk in we are shown to a table and everything just turns up. We don’t get a bill and whoever has to pay leaves the money when we leave.
One time when they had a new waitress, the usual guy came over and told her what we wanted before she gave us the menus.