I've noticed in the midwest the dietitians pretty much always drink milk with lunch. in other locations they rarely do.

I agree that the issue is the "with the meal" part moreso than the request for milk. It seems like the $15-$25/plate restaurants I eat at rarely have my server run my food. Usually my server follows up in a couple minutes, but the person running food may not know that you want milk.

I think you need to grow up to beverages like white russians