My boss recently took the department out for lunch. He treated us to a holiday lunch back in December and wanted to do it again as our department has been doing well. We’re a small group: my boss, our admin, myself, and a coworker who is one of my peers. These lunches have been at fairly nice sit-down restaurants, and my boss always tells us to order whatever we want. I’ve always interpreted that as order whatever I want within reason, and I typically order something similar to what he’s having (i.e., no dessert for me if my boss doesn’t get dessert).