I would not have assumed anything - I would have looked at the menu before agreeing to purchase the bottle.You assume the hundred, the others assume a decimal. The price was not articulated in a manner which one can discriminate what the waiter meant. . 99.99% of Americans who drink wine are more likely to order a $37.50 bottle of wine before a $3750 bottle of wine.Thirty-seven fifty is before the decimal - shame on you for assuming there is a decimal in the price of a bottle of wine at an over-priced restaurant.I'm too frugal to have not known exactly what the wine cost before I agreed to it, but if I ask for a recommendation after saying I don't know much about wine and they suggest a $3k+ bottle, there's likely to be some sort of a scene at my table.
And Sinn, if thirty-seven fifty is $37.50 in our minds, then fifty is $50, not .50. You start before the decimal.
But I also know that grammatically, the word "and" in a number indicates a decimal. I also know a bit about pricing, and would find it very odd for anything to be priced $XXX.50 at a restaurant, where things are likely to be priced in whole dollars at an upscale restaurant, or at the deceptive $XXX.99