We have done several cruises but rarely ask for anything special at dinner. I have seen a few comments about people making fun and interesting requests at dinner. That said, I would love to hear everyone's tips and tricks for changing it up in the dining room.
Here's a trick most people don't use: just because it seems "directed" meals, doesn't mean they are. You can literally start with desert, and go up the menu. You can have a 3-entree dinner, if you choose. You can even order stuff not in the menu at all. You can order a sample of all the deserts. You can order every one's meal and then ask them to take it to your stateroom. Your main and assistant servers will gladly oblige. That said, if you request any of the above, be cool and leave a nicer tip that you usually would.