How to impress the headmaster on Sims 2?

Make sure every room in the house is completely clean. You can also try and get him into the hot tub, that adds extra points. When eating, make sure you have sims at the table with him. Make sure all of their needs is up. And don't schmooze him until near the end. As you already know, it could make you lose points, so it's better to do that last. You don't have to cook lobster, that doesn't matter. Are you calling him to dinner? Or are you just letting him do everything on his own? If not, then that could bea problem too. Good Luck. I usually don't have a problem with the headmaster, they always get in when I do it.