Restaurant Worker Fail

Not-Knowing-When-To-Let-The-Parent-Strategically-Omit-Things-From-The-Menu Fail

Server: "What does he want to drink?" (looking at me and talking about Jack)
Me: "Jack, do you want milk or water?"
Server: "Or a Coke, or Sprite, or Root Beer?"
...later...
Me: "We'll take a kid's ice cream for him."
Server: "What kind?"
Me (with Jack's input): "Vanilla"
Server: "And whipped cream and a cherry and hot fudge and caramel?"

Time-Lapse Fail

Hostess: "How many?"
Me: "Three and a booster seat" (said while pointing at Ryker, who I'm carrying)
H: "Follow me"
(walks 20 feet to a table)
H: "Does he still need a booster?"
("No, lady, in the last 7 seconds he grew two feet and developed the impulse-control necessary to not jump off the chair to get something he sees on the ground.")