At what was otherwise a pleasant dinner recently (in the sky in Toronto, Canada) an ill prepared waiter panicked when I asked him for a wine recommendation and he started to ask me about the price I wanted to pay for a bottle with my dinner. We all know you can't put a price on a great bottle of wine, but to get serious for a moment:
I found it awkward and unnecessary to discuss such a matter in from of the rest of my party. Staff need to be trained properly to confidently discuss the wine cellar.
MY TIP: Ask me about region, pair it with my meal, and direct me to the price with your hand while pointing out suggestions on the wine list.