I know it’s hard out there, but there’s no percentage in hitting on the waitress. You are one of many people who will have this idea today. You will get no points for originality or out-goingness.
Better to chat up the person in line with you at the grocery store, they have no monitary obligation to stay in that grocery store all day, and they might not have been hit on in the last thirty minutes.
Don’t let this advice crush your hopes. The world is ful of people like you. If you can point yourself toward another lonely person like yourself they may be flattered by your attention, the waitress is almost certainly not.
The question of cute waiters is a different one. As a large man I have about fifty pounds on the average man or woman who hits on me. I rarely feel uncomfortable/threatened. Smaller, more attractive men, may feel differently about this. That said, there’s still no percentage in it.