Within the past couple months two situations of similarity have happened to/around me.
The first: Friends and I were at a pretty swanky restaurant/lounge inside a Ritz Carlton hotel. A friend of a friend ordered some shots and the waitress made sure to tell him how much the shots were. It was something absurd like $20 per shot. (I had also payed $5 for ONE cheeseburger slider...but I digress lol). The friend of the friend was offended that the waitress felt the need to tell him the price of the shots, as if she was trying to imply that he couldn't afford the shots. I personally felt that she probably just wanted to let him know that they had hiked up prices, around double of the price of a non-Ritz Carlton hotel lounge type of place.
The second: This weekend at the grocery store. I walked up to the seafood freezer (I know, I shouldn't be buying frozen shrimp I should be buying fresh. I haven't gotten there yet lol) and the fishmonger said "hey, you're looking for the shrimp over here, the shrimp on sale is over here." I thought, why does she think I'm looking for the sale shrimp? I'm no fool, I checked out the sale shrimp, but they weren't pealed, and I hate taking the tails off the shrimp, forget about pealing. So I went back to the other freezer and grabbed my full-priced shrimp. In my mind I questioned, is she assuming I can't afford the full price shrimp, or is she just trying to help me out?
Both cases are sticky situations, because there really is no way to truly understand someone's intentions. Are they trying to save you money, or are they assuming you don't have any?