We kept trying to befriend the servers at the local pub we went to every week. Just as a project. Also because we thought it would be super-cool if, when they saw us come in, they would immediately put in an order for the cheese sticks we'd invariably ask for. We always seemed to get different waitrons, though, and then we stopped going as regularly.
My mother tried that for years at a place we used to go to a lot when I was a kid. She finally gave up trying to become "a regular."
I always want the bartenders to get to know me, but servers not so much. Mostly because I was disinclined to make friends when I *was* a server, so expecting more than like a nod of recognition (and that only if if I go there a lot) feels presumptuous.
There is a person at my neighborhood BaskinRobbins who knows me and my order and there is one person at my work BK who does also, but she is rarely on register anymore.
Wisconsin always ranks high on lists of drunkenness.
And has for a long time. Some years ago (say, around 25), I read a list of the cities with the most bars per capita. The top 5 were all in Wisconsin. OK, smaller cities like Green Bay and La Crosse, but still....
I try not to get into a rut at the deli near my office, because they guys there are really good, and if they know your order, they'll start making it before you even open your mouth to say "Wait, actually, today I was going to have--"
The lovely bartenders at the pool hall where DH plays always remember me. As I walk in the door they are already pouring my glass of wine with a tall ice water on the side. It rocks that they remember.
No, really?
I know, it's crazy unbelievable.
I feel like in this city service familiarity happens a lot. I've rotated among 7-8 coffee/bagel carts on my way to work to avoid creating some kind of expectation. I can't even go to the starbucks in my building anymore b/c I'll get shit for my long absence!
When I was at the bagel shop in NC, we totally would start making up the order as soon as we saw someone's car pull into the lot.
It's kinda' amazing how much getting drunk figures into small town culture in Wisconsin. Also, drinking and driving was no big deal when I was growing up (although I never did it myself). OK, it was not a big deal until kids got killed in drunk driving accidents - then people talked about the problem for a few weeks. But nothing would change.
I always love the cranky diner/convenience store people. The crankier they are, the more I love them. Inevitably, they always turn out to be really nice.