This is a phrase I like to hear. It's more a reiteration of a known fact than a question, and it's only said by people who know you have patterns. There is some comfort in it because it delineates you, gives you more than your standard two dimensions, and shows that someone, somewhere, is paying attention to you.
Most people who dine with me notice that I order the same thing at each place we go. At Semolina's it's chicken parmesan. At La Madeline's, it's tomato basil soup. At Denny's it's the Southern Slam (chicken fried steak and sausage gravy, yum). At Shogun it's usually the rainbow roll, crunchy roll, and shrimp tempura roll. At Juan's Flying Burrito, a local dive that every noder who's visited me here has eaten at lease once, I get chicken quesadillas. And so on. Of course I don't frequent any of these places often enough that the wait staff knows what I want before I order, but that's ok.
People who eat with me often question, with slight irritation, why I don't try something new. I guess I'm a creature of habit and economics. I go for what I know will sate me. I mean, really, any Italian place will have the same ingredients in variations throughout their fare, just like many ethnic restaurants.
In fact, the only time I've had this statement said to me, it wasn't even those words. A bar on Decatur Street in the Quarter called Molly's on the Market was a bar I frequented in a few weeks last summer, and after enough visits, the bartender knew what I wanted and would simply ask, "Abita draft?" It was the kind of rapport you gain as a local, where you can simply point at your empty mug and get a refill, or turn it over and get your tab, usually short a round or two, even though Abita drafts are only a $1.50. But, nowadays, I wouldn't want to be quite so regular at any bar. I'd rather drink at home.