"Slice shops are great, but if you bring your date to one, it might seem as if you don't value their time. So go to Leo instead. This is a sit-down pizza place in Williamsburg, and the personal-sized sourdough pies are mostly in the $20 range. The room feels like a casual, minimalist wine bar, partly due to the fact that they take their wine seriously here. Get a few glasses, split a chopped salad, and eat a few pies, and you should just skate under the $100 threshold. " - neha talreja, bryan kim