Last year we took him to River Cafe. He loved it, but doesn't particularly need or care about $$$$ dinner. I guess I'd just like to give him an experience that is memorable, not necessarily pricey. He lives in Williamsburg so something great there would be nice (we've done Peter Luger to death and we've been to Reynard) maybe El Almacen or Bamonte? Or Manhattan would be fine, probably more lower than upper for his tastes.
We parents are ancient, so prefer someplace where we don't need to bring an ear horn to hear.
Someplace special-ish but not fussy.