Spread cauliflower florets onto a baking sheet; season with salt and pepper.
Bake in the preheated oven for 10 minutes. Stir cauliflower and continue baking until golden brown around the edges, about 20 more minutes.
Heat butter in a small skillet over medium-low heat; cook and stir pine nuts until golden brown, about 5 minutes. Add dates and garlic to pine nuts; cook until dates are softened, 2 to 3 minutes. Season with salt.
Transfer hot cauliflower to a serving bowl. Drizzle pine nut mixture over cauliflower and toss to coat. Serve warm or at room temperature.