Love your name, BandMom! (Former band director here.)
For your anniversary dinner, how about:
The Wave at the Contemporary---very cool atmosphere, fantastic food. I love this place!
Coral Reef---another fantastic atmosphere because of the enormous aquarium...if you don't have a problem with eating fish while watching fish!

Since I always travel with kids, the romantic restaurants haven't been on my radar!
If it were my anniversary, I'd pick California Grill for the great reviews of the food and for the fireworks view.
Your teenager will probably like Sci-Fi Drive-In at DHS...if you stick with burgers, fries, and milkshakes, the food is pretty good. Again, the atmosphere is fantastic here--like an old-fashioned drive-in theater with a 'B' movie loop playing. The tables are fashioned to look like cars.